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•

reviewing, accessing and making recommendations to our board of directors with respect to director compensation;



•

reviewing, approving and overseeing any stock ownership guidelines applicable to executive officers;



•

reviewing and discussing with management the compensation discussion and analysis required to be included in our filings with the SEC and recommending whether the compensation discussion and analysis should be included in such filings;



•

preparing the compensation and HR committee report required by the SEC;



•

making recommendations to our board of directors with respect to management succession planning, including planning with respect to our chief executive officer;

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overseeing compliance with applicable laws and regulations affecting employee compensation and benefits, including regarding stockholder approval of certain executive compensation matters; and



•

reviewing the risks associated with our compensation policies and practices.

Compensation Committee Interlocks and Insider Participation

None of the members of our compensation and HR committee is or has at any time during the past fiscal year been an officer or employee of Ironwood. None of the members of our compensation and HR committee has formerly been an officer of Ironwood. None of our executive officers serve, or in the past fiscal year has served, as a member of the board of directors or compensation committee of any other entity that has one or more executive officers serving as a member of our board of directors or compensation and HR committee. None of the members of our compensation and HR committee had any relationship with us that requires disclosure under any paragraph of Item 404 of Regulation S-K under the Exchange Act.

TheUnder our director compensation policy, effective May 2019, the majority of the compensation that our non-employee directors receive for service on our board of directors is paid in the form of restricted shares of our Class A common stock. Vesting of these shares of restricted stock is contingent on each non-employee director continuing to serve as a member of the board of directors on the last day of each applicable vesting period. If a director ceases serving as a member of our board of directors at any time during the vesting period of a restricted stock award, or RSA, unvested shares will be forfeited on the date of such director's termination of service.

Director Compensation Plan, effective January 2014

From January to May 2019, our directors were compensated pursuant to our prior director compensation plan, which became effective January 1, 2014, or the 2014 Director Compensation Plan. Under this plan, at each annual meeting Shares of stockholders, our non-employee directors received an annual grant of the number of restricted shares of our Class A common stock calculated by dividing (i) the dollar amount for total director compensation approximating the 25th percentile of our current peer group on the date of grant, by (ii) the average closing price of our Class A common stock on the Nasdaq Global Select Market for the six months preceding the month in which the applicable annual meeting of stockholders occurs. Such restricted shares vested 25% on each three-month anniversary of the grant date over a nine-month period and the remaining 25% on the day before the date of the annual meeting of stockholders for the next calendar year.

Under our 2014 Director Compensation Plan, if a non-employee director was elected other than at an annual meeting of our stockholders, on the start date of such non-employee directors service on the board of directors, such non-employee director was granted the number of restricted shares of our Class A common stock granted to non-employee directors at the most recent annual meeting of our stockholders, prorated based on the number of days between the last annual meeting of our stockholders and the date on which the non-employee director began service with us. In connection with their election to the board, on April 1, 2019, each of Mses. Kessler and Moukheibir, Dr. Currie and Mr. Duane were issued 2,995 restricted shares of our Class A common stock, which vested in full on the day before the date of our 2019 annual meeting of stockholders.

In addition, pursuant to our 2014 Director Compensation Plan, the chair of our board and each of the committee chairs received annual compensation of $10,000, payable quarterly in unrestricted stock or cash at the individual director's election. Shares of our Class A common stock issued to our directors2020 under our 2014 Director Compensation Plandirector compensation policy were granted under our Amended and Restated 2010 Employee, Director and Consultant2019 Equity Incentive Plan, or the 2010our 2019 Plan. Further, whether the shares of restricted stock are vested or not, no director may transfer any shares of restricted stock granted pursuant to our 2014 Director Compensation Plan while such person is a director of Ironwood, subject to limited exceptions.

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Under our 2014 Director Compensation Plan, non-employee directors also were reimbursed for reasonable travel and other expenses incurred in connection with attending meetings of the board of directors and its committees.

Non-Employee Director Compensation Policy, effective May 2019

Following a competitive assessment of market data related to non-executive director compensation provided by Pearl Meyer & Partners, LLC, or Pearl Meyer, our compensation consultant at the time, our compensation and HR committee approved our non-employee director compensation policy, or the 2019 Director Compensation Policy, effective in May 2019. Under our 2019 Director Compensation Policy,Plan, the aggregate value of all compensation paid or granted to any director for his or her service as a director in any calendar year may not exceed $600,000.

Under our director compensation policy, at each annual meeting of stockholders, our non-employee directors are granted restricted shares of our Class A common stock with a grant date fair value of $250,000, determined based on the average closing price of our Class A common stock on the Nasdaq Global Select Market (or the stock exchange on which our stock is being actively traded) for the six months preceding the month in which the award is granted, rounded down to the nearest whole share. Such restricted shares vest in full on the date immediately preceding the date of the next annual meeting of stockholders.

UnderEach non-employee director who is first elected to our 2019 Director Compensation Policy,board of directors will, upon his or her initial election, be granted restricted shares of our Class A common stock with a grant date fair value of $250,000, determined based on the average closing price of our Class A common stock on the Nasdaq Global Select Market (or the stock exchange on which our stock is being actively traded) for the six months preceding the month in which the

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award is granted, rounded down to the nearest whole share. Such restricted shares vest in three equal installments on the first three anniversaries of the grant date. In addition, under our director compensation policy, if a non-employee director is elected other than at an annual meeting of our stockholders, then upon his or her initial election to our board of directors, such director will be granted the number of restricted shares of our Class A common stock granted to non-employee directors at the most recent annual meeting of our stockholders, prorated based on the number of days between the last annual meeting of our stockholders and the date on which the non-employee director began service with us. Such restricted shares will vest in full on the date immediately preceding the date of the next annual meeting of stockholders. In addition, each non-employee director who is first elected to our board of directors will, upon his or her initial election, be granted restricted shares of our Class A common stock with a grant date fair value of $250,000, determined based on the average closing price of our Class A common stock on the Nasdaq Global Select Market (or the stock exchange on which our stock is being actively traded) for the six months preceding the month in which the award is granted, rounded down to the nearest whole share. Such restricted shares vest in three equal installments on the first three anniversaries of the grant date.

Shares of restricted stock that were granted to our directors under our 2019 Director Compensation Policy in connection with our 2019 annual meeting of stockholders were granted under our 2010 Plan. After May 2019, shares of restricted stock granted to directors under our 2019 Director Compensation Policy will be granted under our 2019 Equity Incentive Plan, or our 2019 Plan.

In addition to equity grants, each non-employee director receives an annual retainer under our 2019 Director Compensation Policydirector compensation policy for his or her service on our board of directors, as well as additional fees for board chair, committee or committee chair service as follows:

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All cash fees are payable quarterly in arrears and will be prorated for any quarter of partial service, and fees payable under our 2019 Director Compensation Policy were retroactive to April 1, 2019.service. Each non-employee director may elect, prior to January 1 of the year with respect to which such election will be effective, to receive fully vested shares of our Class A common stock at no cost in lieu of his or her annual cash retainer and any additional cash retainers for board chair, committee or committee chair service set forth above. The number of shares of our Class A common stock to be issued will beis determined by dividing the applicable cash retainer(s) the director would be eligible to receive by the closing price of our Class A common stock on the Nasdaq Global Select Market (or the stock exchange on which our stock is being actively traded) on the date the cash fees would otherwise be paid, rounded down to the nearest whole share. Further, non-employee directors are reimbursed for reasonable travel and other expenses incurred in connection with attending meetings of the board of directors and its committees.

Director Compensation Table

The following table sets forth information regarding the compensation earned during the year ended December 31, 2020 by each of our directors who served in 2020 other than Mr. Mallon, our former chief executive officer and former member of our board of directors. Mr. Mallon did not receive compensation for his service on our board of directors.

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Additional Chair Compensation

In connection with Mr. Mallon's resignation as our chief executive officer and a member of our board of directors, Ms. McHugh is spending additional time providing counsel and guidance to the Company's senior leadership team. In connection with her expanded responsibilities and additional time commitment, the compensation and HR committee recommended and the board of directors approved (i) additional cash compensation of $10,000 per month for Ms. McHugh, retroactive to February 15, 2021, for the period in which she serves in this expanded role (as determined by the board of directors), up to a maximum of six months, and (ii) a grant of 2,500 shares of restricted stock, to vest in full in March 2022, subject to Ms. McHugh's continued service on our board of directors through such vesting date. In making its recommendation to the board, the compensation and HR committee took into account a number of factors, including the scope of additional responsibility and anticipated duration and additional time associated with the expanded role, as well as market data provided by our compensation consultant, Rewards Solutions, Aon, which we refer to throughout this proxy statement as 'Aon,' related to board chair compensation.

Director Stock Ownership Guidelines

In May 2019, we instituted stock ownership guidelines as part of our director compensation policy that provide that each non-employee director must accumulate and continuously hold shares of our Class A common stock with a value equal to or greater than three times the amount of the then-current annual retainer paid to the non-employee director for service on our board of directors (excluding any additional board chair, committee, or committee chair retainers). Non-employee directors are required to achieve this level of ownership by the later of (a) May 30, 2021 (the date which is two years from the date of our 2019 annual meeting of stockholders) and (b) two years from the date the individual began service with us, or the Ownership Date.

Compliance with the stock ownership requirements will be measured on the date of the annual meeting of stockholders each year based on the annual retainer then in effect. Following the Ownership Date, until a non-employee director holds the required ownership level and if such director does not hold the number of shares of our Class A common stock to meet the stock ownership requirements at any time thereafter, such director will be required to retain 100% of any shares of our Class A common stock held or received upon the vesting or settlement of equity awards or the exercise of stock options, in each case, net of shares sold to cover applicable taxes and the payment of any exercise or purchase price (if applicable). Further, following the Ownership Date, to the extent a non-employee director does not hold the number of shares of our Class A common stock that meets this threshold, such director will be automatically deemed to have elected to receive any cash retainer for service on our board of directors or a committee thereof in the form of shares of our Class A common stock in an amount that satisfies the threshold shortfall.

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In addition to the stock ownership guidelines described above, the non-employeeno director sharemay transfer restrictions described above under our 2014 Director Compensation Plan remain in effect with respect to any shares of restricted stock granted underpursuant to our director compensation policy that plan.was effective between January 2014 and May 2019, whether the shares of restricted stock are vested or not, while such person is a director of Ironwood, subject to limited exceptions.

We believe our stock ownership guidelines and other transfer restrictions ensure that the interests of our directors, each of whom has equity in the business, are aligned with those of our stockholders and further focus our directors on maximizing long-term value.

Director Compensation Table

The following table sets forth information regarding the compensation earned during the year ended December 31, 2019 by each of our directors who served in 2019 other than (i) Mr. Mallon, our current chief executive officer and current member of our board of directors, (ii) Peter Hecht, our former chief executive officer and former member of board of directors, and (iii) Mark Currie, our former senior vice president, chief scientific officer and president of R&D and current member of our board of directors. Neither Mr. Mallon nor Dr. Hecht received compensation for his service on our board of directors, and Dr. Currie's compensation for service on our board of directors is included in theSummary Compensation Table available elsewhere in this proxy statement.

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On April 1, 2019, each of the non-employee directors who was on our board of directors prior to the date of the Separation held 4,056 unvested shares of our Class A common stock, which represented 25% of the annual restricted stock award of 16,223 shares of our Class A common stock granted on the date of our 2018 annual meeting of stockholders. In connection with the Separation, on April 1, 2019, each such director received a dividend of 405 shares of unrestricted shares of Cyclerion common stock, which amount was determined according to a fixed ratio of one share of Cyclerion common stock for every 10 shares of unvested Ironwood Class A common stock. In addition to receiving 405 shares of Cyclerion common stock, the Separation had the following impact on unvested restricted stock held by directors at the time of the Separation:

Furthermore, the directors who joined Ironwood's board of directors in connection with the Separation (Mses. Kessler and Moukheibir, Dr. Currie and Mr. Duane) also received 405 shares of Cyclerion common stock in addition to the award of 2,995 shares of restricted Ironwood Class A common stock granted on April 1, 2019 in connection with joining our board of directors. Further information on the impact of the Separation on directors' equity is available elsewhere in this proxy statement under the captionCompensation Discussion and Analysis—Equity Impact of the Separation.

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OurIn furtherance of the phased-in board declassification process described elsewhere in this proxy statement under the caption Board Size and Terms, our board of directors has nominated each of our current Class I directors—Dr.Drs. Currie and Messrs. DuaneDenner and Mallon—Mr. Duane—and Class II directors—Mses. Kessler and Moukheibir, Dr. Olanoff and Mr. Shepard—for election at the 20202021 annual meeting. Each of Dr.Drs. Currie, Denner and Olanoff, Messrs. Duane and MallonShepard and Mses. Kessler and Moukheibir has indicated his or her willingness to serve if elected and has consented to be named in the proxy statement. Should any nominee become unavailable for election at the annual meeting, the persons named on the enclosed proxy card as proxy holders may vote all proxies given in response to this solicitation for the election of a substitute nominee chosen by our board of directors.

Vote Required

The threeseven nominees for director with the highest number of affirmative votes will be elected as directors to serve for one year and until their successors are duly elected and qualified or until their death, resignation or removal. Because there is no minimum vote required, abstentions and broker non-votes will not affect the outcome of this proposal.

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Our Executives

The following table sets forth certain information, as of April 21, 2020,22, 2021, with respect to each of our executive officers, other than Mr. Mallon, whose biographical information is included elsewhere in this proxy statement under the captionOur Board of Directors:officers.

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Executive Compensation

Dear Ironwood stockholders,

2019 was a transformative year for Ironwood, underscored by the clear execution from the Ironwood team in driving forward our mission to advance treatment of GI diseases and redefine the standard of care for millions of GI patients. Ironwood is undeniably a very different company today than it was a little over a year ago.

In line with the changes in the company's focus, strategy and leadership team marked by the Separation, we took the opportunity in 2019 to refresh a number of the company's significant plans and policies. At our 2019 annual meeting of stockholders, our stockholders approved our 2019 Equity Incentive Plan, which, among other features that we believe will advance the interests of our stockholders, did not continue the "evergreen" feature of our prior equity incentive plan and limited share recycling under the plan. Additionally, in early 2019, we adopted a clawback policy that provides that our board of directors may recover from our current and former executive offers certain incentive compensation under certain conditions upon a financial restatement. We also instituted formal stock ownership guidelines for directors to further align our director compensation program with the long-term performance of the company.

We also made several important changes to Ironwood's executive compensation program. As we discuss further below, we developed a competitive compensation package to recruit Mark Mallon, who became our CEO in connection with the Separation. We adopted a new executive compensation peer group that includes similarly sized commercial biopharmaceuticals peers (based on market capitalization, median revenue, number of employees, as well as other factors) to align to our post-Separation profile. In addition, for our 2020 executive equity compensation program, we decided to replace stock option grants with performance-based stock unit awards that are designed to further align executive pay with our performance, including stock price performance. We believe this important adjustment will motivate our executive team and further tie our executives' compensation to stockholder value.

As always, we are open to your feedback. Thank you for the privilege of serving as your compensation and HR committee chair.

Sincerely,

Andrew Dreyfus

Chair, Compensation and HR Committee

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Compensation Discussion and Analysis

In 2019 and 2020, ourOur executive equity compensation program has evolved along withcontinued to evolve in 2020 and 2021. One key highlight is the changes to our business marked by the Separation. Two key highlights, described further below, were: (1) the transitionaddition of our chief executive officer in connection with the Separation, and (2) the introduction of performance-based restricted stock units, or PSUs, into our 2020 equity compensation program for our executive officers in lieu of stock options.

1.

Chief Executive Officer Transition
In January 2019, our board of directors hired Mark Mallon to be our chief executive officer, or CEO, effective upon the Separation. Our previous CEO and founder, Peter Hecht, became the CEO of Cyclerion in connection with the Separation. Compensation for Mr. Mallon in 2019 includes certain one-time cash and equity awards granted to compensate him, in part, for outstanding equity he forfeited by leaving his previous employer and therefore is not representative of our expectations for Mr. Mallon's compensation on a go-forward basis. Additional information on Mr. Mallon's compensation is provided under the caption2019 CEO Transition Compensation, below.

2.

Introduction of PSUs into 2020 Executive Equity Program
To further tie executive compensation to corporate performance and stockholder value, in 2020, 50% of annual equity-based compensation awarded to our named executive officers was in the form of PSUs, with the remaining 50% of grants in the form of restricted stock units, or RSUs (based on the grant date fair value of equity awards, with PSU awards measured at target).officers.

In 2020, PSUs replaced stock options in our 2020 executive compensation program to further drive accountabilitytie executive compensation to achieve key milestonescorporate performance and deliver stockholder returns.value. The PSUs awarded in March 2020 to our named executive officers may be earned over a two to three-year performance period based on corporate achievement in three categories: (1) completing clinical pipeline new drug application, or NDA, submissions togaining the U.S. FDA acceptance of one or more additional NDAs through internal development or acquisition of development-stage or commercial-stage programs, (2) achieving target cumulative adjusted organic EBITDA goals, and (3) realizing specified levels of relative stockholder return, or rTSR.

In 2021, to further tie the compensation of our named executive officers to stockholder value, our compensation and HR committee determined to have an rTSR performance goal as the sole PSU performance metric in our 2021 executive equity compensation program, as measured over a three-year performance period against an expanded peer group.

Additional information on our PSU program, including the PSU awards grantedPSUs awarded to our named executive officers in 2020 and 2021 is provided under the captionrespective captions 2020 Annual Equity Awards and Shift to 50% Performance-Based Stock Units2021 Annual Equity Awards, below.

Feedback from stockholders is an essential part of our executive compensation decision-making processes.process. Our company engages with many of our largest stockholders on an annual basis. We invite feedback on a wide variety of topics including corporate strategy, capital allocation, governance, and executive compensation. In 2019,2020, senior management met with nearly allthe majority of Ironwood's largest 20 stockholders, which represented over 90%85% of our outstanding shares as of December 31, 2019.2020. In addition, Alexander J. Denner, Ph.D., who is the chief investment officer of Sarissa Capital Management LP, one of our largest stockholders, joined our board in November 2020.

Our stockholders also have the opportunity to cast a non-binding advisory vote on named executive officer compensation, or a "say-on-pay" vote, every year. This allows our stockholders to provide us with regular, timely and direct input on our executive compensation philosophy, policies and practices. We believe this enables us to further align our compensation programs with our stockholders' interests and to enhance our ability to consider stockholder feedback as part of our annual compensation review process. We sought stockholder input on our executive compensation programsprogram through the say-on-pay vote at our 20192020 annual meeting of stockholders and approximately 87%84% of votes cast by our stockholders voted in support of our named executive officer compensation.

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Compensation Decisions for 2019Named Executive Officers: Goals and 2020Accomplishments

Named Executive Officers for 20192020

This section discusses the principles underlying our policies and decisions with respect to the compensation of our executive officers who are named in theSummary Compensation Table, or our named executive officers. Provided below are material factors we believe are relevant to an analysis of these policies and decisions. Our named executive officers for 2019, which include executives who served the company prior to the Separation,2020 were:

Ironwood executive officers:

•

Mark Mallon, former chief executive officer;



•

Gina Consylman, chief financial officer and senior vice president;



•

Thomas A. McCourt, president;president and



•

Halley E. Gilbert, former chief administrative officer and senior vice president, corporate development.

Ironwood executive officers prior to the Separation:

•

Peter M. Hecht, Ph.D., former interim chief executive officer; and



•

Mark G. Currie, Ph.D., former senior vice president, chief scientific officer, and president of research and development.

Ms. Gilbert resigned from her position with Ironwood effective February 28, 2020. Additional information is provided under the captionPost-Employment Arrangements elsewhere in this proxy statement. Drs. Hecht and Currie each resigned from their respective positions with Ironwood in connection with the Separation in April 2019. Dr. Hecht is no longer an officer or director of Ironwood. Dr. Currie joined our board of directors in April 2019. Additional information is provided under the captionCompensation of Named Executive Officers Who Transitioned to Cyclerion, elsewhere in this proxy statement.

2019 CEO Transition Compensation

Mr. Mallon joined the company as a senior advisor to the board of directors on January 4, 2019 and was named chief executive officer of Ironwood on April 1, 2019 in connection with the completion of the Separation. In order to compensate him, in part, for outstanding equity he forfeited by leaving his previous employer and to align his interests with stockholders, Mr. Mallon's 2019 compensation includes certain one-time cash and equity awards. For this reason, the total compensation that Mr. Mallon received in 2019 is higher than the total compensation that we expect Mr. Mallon will receive on a go-forward basis.

The terms of Mr. Mallon's offer letter provide for the following:

•

an initial base salary of $750,000 per year;



•

an annual bonus target of 75% of his base salary, subject to achievement of individualJason Rickard, chief operating officer and corporate goals;senior vice president; and



•

a one-time new hire bonusMichael Shetzline, M.D., Ph.D., chief medical officer, senior vice president and head of $880,000, subject to certain clawback provisions if he terminates his employment for any reason or the company terminates his employment for Cause (as defined in hisdrug development.

Mr. Rickard and Dr. Shetzline became executive severance agreement described below) within two yearsofficers of his start date;

•

an initial equity grant consisting of:

o

an option to purchase 171,526 shares of our Class A common stock that vest over four years, with 25% of the options vesting on the first anniversary of his start date and 1/48th of the options vesting each month thereafter for the next 36 months;



o

93,036 RSUs that will vest over four years as to 25% of the RSUs on each approximate anniversary of the applicable grant date, and

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•

certain relocation benefits, also subject to certain clawback provisions if effective April 17, 2020. Effective March 12, 2021, Mr. Mallon terminatesresigned from his employment for any reason or the company terminatesposition as Ironwood's chief executive officer and Mr. McCourt became our interim chief executive officer in addition to his employment for Cause, in each case within 12 months following the payment date of his last relocation reimbursement.

continued service as our president. For a description of the impact of the Separation on the number of stock options and RSUs, and the exercise price of stock options, awarded to Mr. Mallon in January 2019 in connection with the commencement of his employment with Ironwood, please seeEquity Impact of the Separation and the footnotes to theGrants of Plan-Based Awards table elsewhere in this proxy statement.

Per his offer letter, upon becoming CEO on April 1, 2019, Mr. Mallon received an additional option to purchase 423,049 shares of our Class A common stock and an additional grant of 206,873 RSUs. As with his initial equity grant, 25% of the options vested on the first anniversary of his start date, with 1/48th of the options vesting each month thereafter for the next 36 months, and the RSUs vest as to 25% of the RSUs on the approximate first four anniversaries of the date of grant. This grant was made on April 1, 2019, the effective date of the Separation. In addition, the company has entered into an indemnification agreement and an executive severance agreement with Mr. Mallon, the terms of each of which are consistent with the forms of indemnification agreement and executive severance arrangements described elsewhere in this proxy statement. Additionalmore information on the factors considered in determining Mr. Mallon's initial compensation package is available under the captionour chief executive officer transition, please see Role of the Compensation and Human Resources CommitteeChief Executive Officer Transition elsewhere in this proxy statement.

The following table presents a summary of the payments made, and value of awards granted, to Mr. Mallon as part of his initial compensation package:

​	​	​	​	​	​	​	​
			New Hire Package (effective January 4, 2019)			CEO Compensation (effective April 1, 2019)
​	​	​	​	​	​	​	​
Base Salary		$	750,000		​		(1)
Sign-on Bonus		$	880,000			—
Restricted Stock Units(2)		$	1,146,204	(4)	$	2,546,607	(4)
Stock Options(3)		$	999,516	(4)	$	2,804,815	(4)
Total		$	3,775,720		$	5,351,422
​	​	​	​	​	​	​	​

(1)  Mr. Mallon's base salary did not change when he became CEO in April 2019 in connection with the Separation.

(2)  Mr. Mallon's RSUs vest over four years as to 25% of the RSUs on each approximate anniversary of the grant date.

(3)  Mr. Mallon's stock options vest as to 25% of the options on the first anniversary of the vesting commencement date and 1/48th of the options each month thereafter for the next 36 months.

(4)  Reflects the fair value of time-based RSU and stock option awards on the date of grant calculated in accordance with Financial Accounting Standards Board issued Accounting Standards Codification Topic 718,Compensation—Stock Compensation. For a discussion of the assumptions used in the valuation of awards made in 2019, including these awards to Mr. Mallon, see Note 15 to our consolidated financial statements for the year ended December 31, 2019 included in our Annual Report on Form 10-K that we filed with the SEC on February 13, 2020. All values reported exclude the effects of potential forfeitures.

Mr. Mallon was not eligible to receive an annual equity award in fiscal year 2019 and instead received initial equity grants in early 2019 as described above.

For information on the cash bonus award paid to Mr. Mallon in 2020 for 2019 performance, as well as Mr. Mallon's base salary increase in 2020 and equity awards granted to Mr. Mallon in 2020, seeNEO Compensation Program, below.

NEO Compensation Program

As in prior years, the three primary elements of our executive compensation program are base salary, cash bonus and long-term equity incentive compensation. Unless the context suggests otherwise, "named executive officers" as used in this section refers to our named executive officers who remained at Ironwood through 2019.

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Goals and Accomplishments

In late 2019, allocations of cash and equity awards to our named executive officersboard, with input from senior management, established what it believed were in large part, dependent upon our meeting certain weightedchallenging corporate performance goals. We work thoughtfully with our compensation and HR committee and other membersgoals for 2020, the achievement of our board of directors to establish what we believe are challenging corporate goals thatwhich would further the accomplishment of our long-term business plan. These goals included LINZESS net sales growth as well as the attainment of certain financial targets, in each case, based on the Company's board-approved operating plan for 2020. In early 2019,2020, our compensation and HR committee approved the relative weighting of our corporate performance goals for 2019. 2020.

Our named executive officers (other than our CEO)(except Mr. Mallon) were evaluated based on the level of achievement of the 20192020 corporate goals and their achievements in 2020, including additional individual goals that contributed toward, and related directly to, the accomplishment of the 20192020 corporate goals. The compensation and HR committee and board determined to equate Mr. Mallon's individual performance with the company's overall corporate performance, and, as a result, assessed Mr. Mallon's performance based on the full setachievement of the 2020 corporate goals.performance goals and accomplishments. Performance measured against the 20192020 corporate and individual goals (as applicable) was used, in part, in determining compensationsalary adjustments and cash bonus awards and adjustments for our named executive officers in early 2020.2021.

The 2019As described in more detail elsewhere in this proxy statement under Compensation Determination Process, beginning in 2021, our board became responsible for assessing the Company's performance against its pre-determined corporate goals, and the level of achievement against these goals, as determined by our compensation and HR committee, was as follows:

​	​	​	​	​	​	​	​	​	​	​	​
Corporate Goal		Stockholder Impact		Achievements			Target Percentage (%)			Actual Level of Achievement (%)
​	​	​	​	​	​	​	​	​	​	​	​
Grow the value of our IBS/constipation franchise		Grows the revenue base		• Delivered target U.S. LINZESS net sales with compliance excellence • Obtained top-line Phase III abdominal symptom data and executed a compliant marketing plan to achieve 2019 volume targets			40	%		51	%
​	​	​	​	​	​	​	​	​	​	​	​
Create value from our innovative pipeline		Advances future business growth and profitability		• Advanced enrollment in Phase III pivotal studies in rGERD, including enrollment of patients with erosive esophagitis • Initiated MD-7246 Phase II study of abdominal pain associated with IBS-D and completed study enrollment well in advance of goals			30	%		22	%
​	​	​	​	​	​	​	​	​	​	​	​
Strengthen our financial profile		Transitions to cash generation		• Delivered target adjusted EBITDA from continuing operations* • Raised a total of $400 million in convertible notes due 2024 and 2026, and used proceeds to pay for associated capped call transactions, redeem all the outstanding principal balance of our 8.375% notes due 2026, and repurchase $215 million aggregate principal amount of our convertible notes due 2022			15	%		15	%
​	​	​	​	​	​	​	​	​	​	​	​
Achieve value-creating corporate milestones		Supports potential for long-term growth and profitability		• Successfully executed the Separation • Entered into commercial partnerships in 2019 with Allergan to continue to promote Allergan's VIBERZI® and with Alnylam for Alnylam's GIVLAARI™			15	%		18	%
​	​	​	​	​	​	​	​	​	​	​	​
				Totals			100	%		106	%
​	​	​	​	​	​	​	​	​	​	​	​
		Stretch Goals for Additional Potential Achievement					50	%		24	%
​	​	​	​	​	​	​	​	​	​	​	​
				TOTALS			150	%		130	%
​	​	​	​	​	​	​	​	​	​	​	​

* Adjusted EBITDA from continuing operations was calculated by subtracting net interest expense, taxes, depreciation, amortization, fair value of remeasurement of contingent consideration, mark-to-market adjustments on derivatives related to Ironwood's 2.25% convertible notes due 2022, impairment of intangibles, restructuring expenses, separation expenses, and loss on extinguishment of debt from GAAP net income (loss) from continuing operations.

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In addition to the above corporate goals, the company achieved certain stretch goalsgoals. Thus, in 2019, including higher LINZESS brand profitability compared to target and outperformance relative to adjusted EBITDA from continuing operations expectations. As a result,January 2021, our compensation and HR committeeboard determined that the 20192020 company performance achievement multiplier, which was used as a key consideration in determining executive compensation awarded for 20192020 performance, was 130%101%. When assessing corporate performance for 2020, our board noted that certain of our corporate goals for 2020 were met or exceeded despite the challenges posed by the COVID-19 pandemic. No COVID-19-related adjustments were made to goals, expectations or compensation targets for our named executive officers in 2020.

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The level of achievement against our 2020 corporate performance goals, as determined by our board in early 2021, was as follows:

​	​	​	​	​	​	​	​	​	​	​	​
Corporate Goal		Stockholder Impact		Achievements			Target Percentage (%)			Actual Level of Achievement (%)
​	​	​	​	​	​	​	​	​	​	​	​
Drive LINZESS Growth		Grows the revenue base		• Exceeded target U.S. LINZESS net sales of $892 million with compliance excellence • Obtained U.S. FDA approval of sNDA to include IBS-C overall abdominal symptoms data LINZESS label			30	%		40	%
​	​	​	​	​	​	​	​	​	​	​	​
Advance our Pipeline		Advances future business growth and profitability		• Obtained Phase III data from IW-3718 program and made data-driven "go/no go" decision to discontinue development of IW-3718 • Obtained Phase II data from MD-7246 clinical trial ahead of schedule and made data-driven decision to discontinue development of MD-7246			30	%		30	%
​	​	​	​	​	​	​	​	​	​	​	​
Expand our impact in GI		Supports potential for long-term growth and profitability		• In connection with a U.S. disease education and promotional agreement with Alnylam Pharmaceuticals, Inc., Ironwood efforts contributed to >25 patients starting on GIVLAARI® (givosiran) treatment			20	%		6	%
​	​	​	​	​	​	​	​	​	​	​	​
Invigorate Ironwood		Helps to attract, motivate and retain top talent		• Built new GI capabilities and expertise • Strengthened and advanced equality, diversity & inclusion (ED&I) initiatives			5	%		5	%
​	​	​	​	​	​	​	​	​	​	​	​
Strengthen our financial profile		Enables Ironwood to invest thoughtfully without reliance on capital markets		• Exceeded target revenue of $372 million, target adjusted EBITDA* of $105 million, and target cash from operations of $135 million • Delivered 2nd full year of profitability			15	%		20	%
​	​	​	​	​	​	​	​	​	​	​	​
				Totals			100	%		101	%
​	​	​	​	​	​	​	​	​	​	​	​
		Stretch Goals for Additional Potential Achievement					50	%		0	%
​	​	​	​	​	​	​	​	​	​	​	​
				TOTALS			150	%		101	%
​	​	​	​	​	​	​	​	​	​	​	​

* Adjusted EBITDA from continuing operations was calculated by subtracting net interest expense, income taxes, depreciation, amortization, mark-to-market adjustments on derivatives related to Ironwood's 2.25% convertible notes due 2022, restructuring expenses, from GAAP net income (loss) from continuing operations.

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In support of the 20192020 corporate goals identified above, our compensation and HR committeeat the beginning of 2020 as well as throughout 2020 in response to changes in the business, Mr. Mallon assigned ownership of a specific subset of goals to each of our named executive officers, as follows:

​	​	​
Name		Summary of Individual Goals
​	​	​
Gina Consylman		• Deliver target adjusted EBITDA from continuing operations • Execute onGenerate cash from operations, requiring substantial management judgment and discipline, including efficient decision-making and cost-center level accountability across all aspects of the Separation, including setting up two independent companies with separate financial systemsbusiness • Strengthen our balance sheetEvaluate inorganic opportunities in effort to drive further value including completing three GI deep dives and improve cost of capitalidentifying a potential mid/late-stage asset • Improve our financial performance monitoring capabilities • Gain board approval ofLead corporate strategy, investor relations and corporate communications activities to gain alignment on a refreshed strategic framework to drive future growth
​	​	​
Halley E. Gilbert		• Execute on the Separation, including establishing transition services and executing development plan • Establish a commercial partnership that increases enterprise value • Maintain our culture of compliance • Provide high quality intellectual property advice, including relating to abbreviated new drug application litigation ongoing in 2019corporate strategy
​	​	​
Thomas A. McCourt		• Deliver target LINZESS net trade sales with compliance excellenceand total revenue targets • Strengthen LINZESS profile with releaseGrow the value of Phase III abdominal symptom dataIW-3718 in refractory GERD and advance MD-7246 IBS-D pain program and additional early-stage pipeline assets • Refresh LINZESS life cycle management plan inMaximize the value delivered from our salesforce optimizing our GIVLAARI partnership with AllerganAlnylam Pharmaceuticals, Inc. and securing an additional commercial product • Advance enrollment of the Phase III clinical studies of IW-3718Establish one new innovative payer contract working with our commercial partner for LINZESS, AbbVie, during 2020 in rGERDan effort to stabilize and ultimately improve net price • Initiate MD-7246 Phase II abdominal pain studyBuild needed capabilities aimed at becoming the recognized leader in IBS-D patients, positioningGI including optimizing our sales force, enhancing healthcare provider engagement, and certain talent upgrades
​	​	​
Jason Rickard		• Lead the company's response to deliver top-line data readout in 2020the COVID pandemic* • Strengthen commercialFacilitate the smooth transition of all linaclotide international supply responsibilities to AstraZeneca AB and Astellas Pharma Inc. • Execute operations relative to IW-3718 and MD-7246 programs including pharmaceutical development, supply chain and GxP quality • Further IT operational efficiencies including optimizing certain enterprise systems • Lead the company's reduction in force effort* • Deliver on our people priorities; inspire through our mission and strategy, advance our equality, diversity and inclusion program and grow/challenge our people with targeted individual development programs
​	​	​
Michael Shetzline, M.D., Ph.D.		• Gain approval of sNDA to reflect results of Phase IIIb trial in LINZESS label, negotiating and securing additional language with the U.S. FDA documenting the relief of overall abdominal symptoms of IBS-C in the LINZESS product label • Obtain IW-3718 top-line Phase III data in refractory GERD, implementing programs to accelerate screening and participant recruitment and gaining U.S. FDA consent to certain trial design changes to strengthen the overall program • Make go / no go decision on IW-3718 based on the clinical outcomes with a thorough assessment on strategic implications under various scenarios • Complete the data analysis and make go / no go decision on MD-7246 based on the clinical outcomes with a thorough assessment on strategic implications under various scenarios • Co-lead the GI landscape assessment to evaluate the existence and accessibility of GI assets across the industry, identifying and prioritizing potential assets • Establish a team of world class experts and trusted opinion leaders in gastroenterology to provide valued insight and advice to the drug development capabilities through completion of a number of targeted program initiativesand commercial teams
​	​	​

* Additional goal added during 2020 in response to changing business needs.

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34    Ironwood

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In early 2020,2021, Mr. Mallon evaluated the individual performance in 20192020 of each of the named executive officers listed above(other than himself) and provided feedback and made recommendations to our compensation and HR committee. The committee then determined the named executive officers' compensation, taking into account Ironwood's level of achievement of its corporate goals as well asdetermined by our board and the fact that each named executive officer exceededstrongly met or far exceeded performance expectations for 2019.2020, as well as peer group and other market data from the competitive assessment undertaken by our compensation and HR committee's independent compensation consultant, Aon, as discussed below.

Additional information on the basis for compensation decisions in 2019about 2020 compensation relating to our named executive officers is available throughout this section and elsewhere in this proxy statement under the captionsRole of the Compensation and Human ResourcesHR Committee andRole of the Compensation Consultant: Benchmarking and Peer Group Analysis.

Compensation Decisions for 2020 and 2021

Named Executive Officer Compensation Program

As in prior years, the three primary elements of our executive compensation program are base salary, cash bonus and long-term equity incentive compensation.

Base Salary

Base salaries are determined at an executive's commencement of employment and are generally re-evaluated annually and adjusted, if warranted, to realign salaries with market levels or in connection with promotions or other changes in role and to reflect the performance of the named executive officer. In determining whether to adjust or recommend an adjustment to a named executive officer's base salary, our compensation and HR committee takes into consideration factors such as our corporate performance in prior years, general economic factors and compensation parity among our named executive officers, as well as the abilities, performance and experience of the named executive officer. Our compensation and HR committee also reviews our named executive officers' past compensation at the company and market data. Beginning in 2021, our compensation and HR committee recommends, and our board approves, compensation determinations for our chief executive officer. Please seeRole of the Compensation and HR Committee and Role of the Compensation Consultant: Benchmarking and Peer Group Analysis for further information.

In January 2020, our compensation and HR committee reviewed and approved base salaries for 2020 for Mr. Mallon, Ms. Consylman and Mr. McCourt. The increases in base salary for Mr. Mallon, Ms. Consylman and Mr. McCourt were based on our compensation and HR committee's determination that we achieved 130% of our corporate goals in 2019 and, in the case of Ms. Consylman and Mr. McCourt, recognition that each executive far exceeded all or substantially all of her or his respective individual goals for 2019. These base salary determinations also took into account peer group and other market data from the Aon competitive assessment discussed below. In addition, the increase in base salary for Mr. McCourt in 2020 includes an adjustment to better align his base salary with the external market in his role as the company's president. In April 2020, the compensation and HR committee also ratified and approved 2020 base salaries for Mr. Rickard and Dr. Shetzline, in connection with their respective designation as executive officers of the company. In ratifying and approving Mr. Rickard and Dr. Shetzline's respective base salaries, our compensation and HR committee considered a number of factors, including each of Mr. Rickard and Dr. Shetzline's backgrounds, the compensation paid to executives in similar positions at our peer group companies and other benchmark data, and executive compensation parity within Ironwood, as well as input from Aon.

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20202021  Proxy Statement    35

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Base salary information for 2020 compared to base salary information for 2019 for our named executive officers, as applicable, is as follows:

​

​

​

​

​

​

​

​

​

​

Named Executive Officer

​

2019 Base Salary

​

2020 Base Salary

​

Increase ($)

​

Increase (%)

​

​

​

​

​

​

​

​

​

​

​

Mark Mallon

​

​

$

750,000

​

​

​

$

772,500

​

​

​

$

22,500

​

​

​

3

%

​

Gina Consylman

​

​

$

480,000

​

​

​

$

494,400

​

​

​

$

14,400

​

​

​

3

%

​

Thomas McCourt

​

​

$

520,000

​

​

​

$

556,400

​

​

​

$

36,400

​

​

​

7

%

​

Jason Rickard

​

​

*

​

​

​

$

456,750

​

​

​

*

​

​

​

*

​

​

Michael Shetzline, M.D., Ph.D.

​

​

*

​

​

​

$

448,050

​

​

​

*

​

​

​

*

​

​

​

​

​

​

​

​

​

​

​

​

* Mr. Rickard and Dr. Shetzline became executive officers of Ironwood effective April 17, 2020.

In January 2019,February 2021, our compensation and HR committee reviewed and approved the following base salaries for 2019 for our named executive officers (other than Mr. Mallon, whose compensation was set when he commenced service with us, as described above): Ms. Consylman received a $65,000 increase infor 2021. Base salary information for 2021 compared to base salary from $415,000 to $480,000, Ms. Gilbert received a $20,000 increase in base salary from $460,000 to $480,000, and Mr. McCourt received a $20,000 increase from $465,000 to $485,000. The increase in base salaryinformation for Ms. Consylman, Ms. Gilbert and Mr. McCourt was based on our compensation and HR committee's determination that we achieved 100%2020 for each of our corporate goals in 2018 and in recognition that each such named executive officer met or exceeded all or substantially all of his or her respective individual goals for 2018. This determination also took into account peer group and other market data from the Pearl Meyer competitive assessment discussed below. In addition, the increase in base salary for Ms. Consylman in 2019 also includes adjustments to better align her base salary with the external market and her internal peers. In May 2019, Mr. McCourt received a $35,000 increase in base salary from $485,000 to $520,000 in connection with his promotion to president, which increase was effectiveofficers is as of April 1, 2019.follows:

​

​

​

​

​

​

​

​

​

​

Named Executive Officer

​

2020 Base Salary

​

2021 Base Salary

​

Increase ($)

​

Increase (%)

​

​

​

​

​

​

​

​

​

​

​

Gina Consylman

​

​

$

494,400

​

​

​

$

509,400

​

​

​

$

15,000

​

​

​

3

%

​

Thomas McCourt

​

​

$

556,400

​

​

​

$

573,200

​

​

​

$

16,800

​

​

​

3

%

​

Jason Rickard

​

​

$

456,750

​

​

​

$

484,200

​

​

​

$

27,450

​

​

​

6

%

​

Michael Shetzline, M.D., Ph.D.

​

​

$

448,050

​

​

​

$

484,000

​

​

​

$

35,949

​

​

​

8

%

​

​

​

​

​

​

​

​

​

​

​

In January 2020, our compensation and HR committee reviewed and approved the following base salaries for 2020: Mr. Mallon received a $22,500 increase in base salary from $750,000 to $772,500, Ms. Consylman received a $14,400 increase in base salary from $480,000 to $494,400, and Mr. McCourt received a $36,400 increase from $520,000 to $556,400. The compensation and HR committee did not recommend, and the board did not increase, Ms. Gilbert'sMr. Mallon's base salary in 2021 because Ms. GilbertMr. Mallon had provided notice of herhis intent to resign from the company at the time salary determinations for 2021 were made. Information on Mr. McCourt's salary for his service as our interim chief executive officer beginning in February 2020.March 2021 is available elsewhere in this proxy statement under the caption Chief Executive Officer Transition.

Cash Bonus

Our cash bonus program is designed to reward the achievement of our annual corporate goals and individual goals. The program is also intended to foster and support our performance-driven culture by setting clear, high-value goals, rewarding outstanding performers and making sure our employees know clearly that we value their contributions. Each cashtarget bonus award, expressed as a percentage of an executive's base salary, is madedetermined annually and is based on the extent to which we achieved our corporate goals for the preceding year, as well as the executive's individual performance in that year against his or her individual goals. In 2019,2020, Mr. Mallon's target bonus was 75% of his base salary, Ms. Consylman's target bonus was 50% of her base salary, and Mr. McCourt's target bonus was 60% of his base salary,salary. Upon their designation as executive officers in April 2020, the compensation and Mses. ConsylmanHR committee ratified and Gilbert'sapproved Mr. Rickard and Dr. Shetzline's target bonus percentages for 2020, which for Mr. Rickard was 50% of their respectivehis base salaries.salary and for Dr. Shetzline was 40% of his base salary. We believe that these target bonus percentages align the target cash compensation of our named executive officers with that of our peers, place appropriate emphasis on achievement of our annual performance objectives and facilitate recruiting, retaining and motivating our executive officers.

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For each of our named executive officers, 70% of each cash bonus award paid in 20202021 for 20192020 performance was based solely on the achievement of our corporate goals and 30% was based on the named executive officer's achievement of his or her individual goals, which, as described above for named executive officers other than Mr. Mallon, included specific accountability for certain of our corporate goals. In determiningrecommending for approval by the board the amount of Mr. Mallon's cash bonus to be paid in 2021 for 2020 for 2019 performance, theour compensation and HR committee equated Mr. Mallon's individual performance to the company's 20192020 performance achievement multiplier of 130%101%.

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36    Ironwood

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Table The board reviewed and followed this recommendation in approving Mr. Mallon's cash bonus award for 2020 performance, which he remained eligible to receive as a result of Contentsbeing employed as our chief executive officer on the date cash bonus awards for 2020 performance were paid in 2021.

​

​

The following summarizes the calculation of our named executive officers' cash bonus awards paid in 2021 for 2020 for 2019 performance:

​

​

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​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

Component Calculation

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

Company Performance Only Component (Weighted 70%)

70% Weighting

×

Target Bonus

×

Corporate Performance Achievement Multiplier

=

Company Performance Only Component Payout

+

Company and Individual Performance Component (Weighted 30%)

30% Weighting

×

Target Bonus

×

Corporate Performance Achievement Multiplier

×

Individual Performance Achievement Multiplier

=

Company and Individual Performance Component Payout

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

Total Annual Bonus Payout

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

This approach was intended to closely align cash bonus awards toaward payouts with the achievement of our corporate goals, while taking into account individual performance (or, in the case of Mr. Mallon, equating company performance with individual performance) and providing equity and transparency to the calculation of our executive bonuses.making bonus determinations in a transparent way. As described above, the company performance achievement multiplier for 20192020 was 130%101%. In February 2020,2021, our compensation and HR committee determined that each of our named executive officers, exceededother than Mr. Mallon, strongly met or far exceeded performance expectations for 2019,2020, resulting in the following individual performance achievement multipliers:multipliers and bonus ratios to target bonus percentage (after applying the 70%/30% weighting and taking into account the company performance achievement multiplier of 101%): Ms. Consylman, 150%120% individual performance, resulting in actual bonus to target bonus ratio of 107%; Ms. Gilbert, 130% and Mr. McCourt, 120% individual performance, resulting in actual bonus to target bonus ratio of 107%; Mr. Rickard, 140% individual performance, resulting in actual bonus to target bonus ratio of 113%; and Dr. Shetzline, 125% individual performance, resulting in actual bonus to target bonus ratio of 109%. OurAs described above, our compensation and HR committee also recommended and our board determined that Mr. Mallon's individual performance achievement multiplier was 130%101% on the basis that such multiplier was equal to the 130% corporate performance achievement multiplier.multiplier of 101%. The compensation and HR committee (or the board, in the case of Mr. Mallon) reviewed and approved the following bonuses for 20192020 performance for our named executive officers:

​	​	​	​	​	​	​				​
Named Executive Officer			Annual Cash Bonus for 2019 Performance		​	Annual Cash Bonus for 2020 Performance				​
​	​	​	​	​	​	​				​
Mark Mallon		$	797,063		​	​	$	585,169	​	​
Gina Consylman		$	358,800		​	​	$	264,652	​	​
Halley E. Gilbert		$	340,080
Thomas A. McCourt		$	454,272
Thomas McCourt					​	​	$	357,409	​	​
Jason Rickard					​	​	$	258,338	​	​
Michael Shetzline, M.D., Ph.D.					​	​	$	194,588	​	​
​	​	​	​	​	​	​				​

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In addition to the annual cash bonus for 20192020 performance described above, in May 2019, Mses. Consylman and Gilbert eachJanuary 2020, Dr. Shetzline received a special $250,000 cash award in recognitionpayment of their significant contributions to and performance in connection with$100,000, reflecting the Separation and, with respect to Ms. Gilbert, for her expanded role overseeing our corporate development function.second installment of his sign-on bonus under the terms of his employment offer letter.

Long-Term Equity Awards

Long-term equity incentive compensation granted in 2020 represented, on average, approximately 70% of each named executive officer's total compensation for the year (based on the grant date fair value of equity awards, with PSU awards measured at target). We believe this emphasis on equity, and particularly performance-based equity, strongly reinforces the principle of "pay for performance", and closely ties our executives' pay outcomes to stockholder value creation. We also use equity awards as our incentive vehicle for long-term compensation to attract, reward and motivateretain our named executive officers in a manner that is intendedand to align theirthe interests of our named executive officers with those of our stockholders. We typically grant equity awards in the first quarter of each year based on our performance in the prior year. Throughout the year, our compensation and HR committee may award additional grants as circumstances warrant. Our compensation and HR committee does not apply a rigid formula in allocating equity awards to our named executive officers as a group or to any particular named executive officer, but sets an equity pool each year based on achievement of our corporate goals forpeer group and other market data from the prior year, which for 2018 was 100% of our corporate goals, including certain stretch goals, and our expectations for future performance. Individual equity award amounts are then determined based on, among other factors,Aon competitive assessment discussed below. In addition to peer

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group and market data, and our compensation and HR committee adjusts these amounts after consideringalso considers other factors, including input from compensation advisorsAon and amount of unvested equity held by a named executive officer, in determining the size of individual performance.equity awards.

20192020 Annual Equity Awards

In 2019, our named executive officers had a choice of the composition of their annual equity awards and could select from the following choices: 100% stock options; 75% stock options and 25% RSUs; or 50% stock options and 50% RSUs. The size of executive equity grants was determined based on the factors described above and each of our named executive officers, other than Mr. Mallon (who joined Ironwood in January 2019), was awarded the following stock option and RSU awards under our Amended and Restated 2010 Employee, Director and Consultant Equity Incentive Plan, or 2010 Plan, in January 2019:

Named Executive Officer			2019 Annual Stock Option Grant (# of Shares of Class A common stock Subject to Stock Options)			2019 Annual RSU Grant (# of Shares of Class A common stock Subject to RSUs)
​	​	​	​	​	​	​	​
Gina Consylman		​	145,000		​	72,500
Halley E. Gilbert			145,000			72,500
Thomas A. McCourt		​	345,000		​	—
​	​	​	​	​	​	​	​

On the date of grant, the stock options had an exercise price of $12.90 per share (the closing price of our Class A common stock on the Nasdaq Global Select Market on the grant date). Generally subject to the executives' continued employment with the company. The stock options vest monthly over four years as to 1/48th of the options following the date of grant and the RSUs vest as to 25% of the RSUs on each approximate anniversary of the date they were granted. For a description of the impact of the Separation on the number of stock options and RSUs, and the exercise price of stock options, awarded to our named executive officers in January 2019, please seeEquity Impact of the Separation and the footnotes to theGrants of Plan-Based Awards table elsewhere in this proxy statement.

In connection with the Separation in April 2019, Mr. McCourt was promoted to president and was granted an additional 45,704 stock options and 22,852 RSUs, each for shares of our Class A common stock under our 2010 Plan. The stock options have an exercise price of $11.78 per share (the closing price of our Class A common stock on the Nasdaq Global Select Market on the grant date). Subject to Mr. McCourt's continued employment with the company, the stock options will vest monthly over four years as to 1/48th of the options following the date of Mr. McCourt's promotion, and the RSUs will vest as to 25% of the RSUs on each approximate anniversary of the date they were granted.

Equity awards granted to Mr. Mallon in 2019 are described above under the caption2019 CEO Transition Compensation.

Retention Grants

In December 2019, we made special retention awards of RSUs to our named executive officers, other than Mr. Mallon, which vest as to 100% of the RSUs after two years generally subject to the executives' continued employment with the company. Mses. Consylman and Gilbert received 41,150 RSUs and Mr. McCourt received 115,220 RSUs. In establishing the size of these grants, our compensation consultant, Rewards Solutions, Aon (or Aon), presented peer group data and assisted2020, our compensation and HR committee with approximating the value that another organization could potentially offer in a sign-on equity grantdecided to recruit our executive talent. In connection with her resignation from the company in February 2020, the 41,150 RSUs granted to Ms. Gilbert in December 2019 terminated in their entirety.

2020 Equity Awards and Shift to 50% Performance-Based Stock Units

We believe that creating long-term shareholder value requires our executive team to balance their efforts on driving LINZESS growth and advancing our late-stage development programs while at the same time progressing on milestones necessary to expand future product offerings. Accordingly,introduce PSUs into our 2020 executive equity compensation program is comprised of 50% PSUsin an effort drive accountability to achieve key milestones and 50% RSUs.deliver stockholder returns. In introducing PSUs in 2020 and providing for an equal mixnumber of PSUs and RSUs by grant

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date fair value (with PSUs measured at target),to our named executive officers, the compensation and HR committee sought to design a 2020 executive equity compensation program that provides the appropriate combination of equity awards to incentivize performance, align executive interests with those of our stockholders, and encourage executive retention.

As in 2019, long-term equity incentive compensation grantedTo facilitate the transition in 2020 is expectedfrom the use of stock options, which vested on a monthly basis, to represent a majority of eachPSUs, which were subject to two or three year performance periods, 2020 RSU grants to our named executive officer's total compensation forofficers vest as to approximately 33% of the year (basedunderlying shares on each approximate anniversary of the grant date fair value of equity awards, with PSU awards measured at target). We believe this emphasis on equity, and particularly performance-based equity, strongly reinforces the principle of "pay for performance," and closely ties our executives' pay outcomes to stockholder value creation.

Goalsaward. Performance goals underlying 2020 PSU awards were set tomust be achieved over a two to three-year performance period based, in part, on our long-range operating plan. Our compensation and HR committee selected the following performance goals for our 2020 PSU awards, which we believewere intended to drive executive accountability for delivering value to our stockholders:

1)

Gaining the U.S. FDA's acceptance of one or more additional NDAs;NDAs through internal development or acquisition of development-stage or commercial-stage programs, or NDA Acceptance PSUs;

2)

Growing revenue and controlling expenses as measured by cumulative adjusted organic EBITDA;EBITDA, or Adjusted EBITDA PSUs; and

3)

Realizing rTSR goals.goals, or 2020 rTSR PSUs.

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The 2020 PSUs use the following metrics, weighting and vesting opportunity:

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​

Performance Metric

Weight

Performance Period

Threshold Goals (50% attainment)

Target Goals (100% attainment)

Stretch Goals (200% attainment)

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​

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​

​

​

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NDA Acceptance PSUs

40%

Ending December 2022

N/A

Acceptance by the U.S. FDA of an NDA for IW- 3718IW-3718 or other internal or external development program

Acceptance by the U.S. FDA of two NDAs, including IW-3718 and/or other internal or external development programs

Adjusted EBITDA PSUs

30%

2020 - 2021 Cumulative Target

Threshold cumulative adjusted organic EBITDA through 2021

Target cumulative adjusted organic EBITDA through 2021

Stretch target cumulative adjusted organic EBITDA through 2021

2020 rTSR PSUs

30%

Ending December 2022

rTSR at the 25th percentile compared to rTSR peer group through 2022

rTSR at the 50th percentile compared to rTSR peer group through 2022

rTSR at the 75th percentile compared to rTSR peer group through 2022

​

​

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​

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​

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Our compensation consultant, Aon, assisted our compensation and HR Committeecommittee with assessing our profile and market characteristics versus several potential benchmarks and then identifying an expandeda peer group of commercial biopharmaceuticalpharmaceutical and biotechnology companies for purposes of the 2020 rTSR measurement goal under these PSUs. At the time they were designated, the peer group identified for the purposes of the 2020 rTSR PSUs ranged between $750 million and $10 billion in market capitalization; Ironwood's market capitalization at that time was at the 47^th percentile relative to this custom peer group. Our compensation and HR committee then approved the following custom rTSR measurement peer group for the 2020 rTSR PSUs, which included all of our executive compensation peers at the time the custom rTSR peer group was designated:

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committee then approved the following custom, rTSR measurement peer group, which includes all of our current executive compensation peers:

ACADIA Pharmaceuticals, Inc.		Ionis Pharmaceuticals, Inc.
Aerie Pharmaceuticals, Inc.		Jazz Pharmaceuticals plc
Agios Pharmaceuticals, Inc.		Karyopharm Therapeutics Inc.
Akcea Therapeutics, Inc.		Ligand Pharmaceuticals Incorporated
Akebia Therapeutics, Inc.		Momenta Pharmaceuticals, Inc.
Alkermes plc		OPKO Health, Inc.
Amicus Therapeutics, Inc.		Pacira BioSciences, Inc.
Amphastar Pharmaceuticals, Inc.		Perrigo Company plc
bluebird bio, Inc.		Portola Pharmaceuticals, Inc.
Blueprint Medicines Corporation		Prestige Consumer Healthcare Inc.
Catalent, Inc.		PTC Therapeutics, Inc.
Coherus BioSciences, Inc.		Radius Health, Inc.
Corcept Therapeutics Incorporated		Sage Therapeutics, Inc.
Eagle Pharmaceuticals, Inc.		Sarepta Therapeutics, Inc.
Emergent BioSolutions Inc.		Spectrum Pharmaceuticals, Inc.
Endo International plc		Supernus Pharmaceuticals, Inc.
Exelixis, Inc.		Taro Pharmaceutical Industries Ltd.
Flexion Therapeutics, Inc.		Theravance Biopharma, Inc.
GW Pharmaceuticals plc		Ultragenyx Pharmaceutical Inc.
Halozyme Therapeutics, Inc.		United Therapeutics Corporation
Heron Therapeutics, Inc.		Vanda Pharmaceuticals Inc.
Horizon Therapeutics Public Limited Company		Veracyte, Inc.
Insmed Incorporated		Vericel Corporation
Intercept Pharmaceuticals, Inc.
​	​	​

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In February 2020, our named executive officers were granted the following equity awards under our 2019 Equity Incentive Plan, or 2019 Plan:

Named Executive Officer

2020 Annual PSU Grant (# of Shares of Class A common stock Subject to PSUs) (at target)

2020 Annual RSU Grant (# of Shares of Class A common stock Subject to RSUs)

​

2020 Annual PSU Grant (# of Shares of Class A common stock Subject to PSUs) (at target)

​

2020 Annual RSU Grant (# of Shares of Class A common stock Subject to RSUs)

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Mark Mallon

​

221,061

​

221,061

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221,061

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221,061

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Gina Consylman

68,327

68,327

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68,327

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68,327

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Halley E. Gilbert

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—

​

—

Thomas A. McCourt

100,482

100,482

Thomas McCourt

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100,482

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100,482

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Jason Rickard

​

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60,289

​

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60,289

​

​

Michael Shetzline, M.D., Ph.D.

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48,875

*

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48,875

*

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​

Equity awards* Comprised of 28,135 PSUs and 28,135 RSUs granted to Messrs. Mallonin February 2020, as well as an additional 20,740 PSUs and McCourt had target values based approximately on20,740 RSUs granted in April 2020 in connection with Dr. Shetzline's designation as an executive officer of the peer group 50^th percentile. Equity awards granted to Ms. Consylman were 13% above the 50^th percentile in recognition of her outstanding performance in 2019.company. The compensation and HR committee did not make anapproved this additional award based on Aon's input and in order to further align Dr. Shetzline's unvested equity awardposition with that of the other executive officers. The PSUs and RSUs granted to Ms. Gilbert because she had provided noticeDr. Shetzline in April 2020 were subject to the same terms as described above related to equity grants to named executive officers in 2020.

In connection with their designation as executive officers of her intent to resign from the company in April 2020, the compensation and HR committee ratified and approved the PSU and RSU grants listed above for Mr. Rickard and Dr. Shetzline.

As of the date of this proxy statement, none of the PSUs granted in 2020 had vested.

2021 Annual Equity Awards

In early 2021, our compensation and HR committee again determined, as it had in 2020, that the annual long-term equity incentive compensation awards for our named executive officers should consist of an approximately even number of PSUs and RSUs. The compensation and HR committee chose rTSR performance as the sole PSU performance metric in our 2021 executive equity compensation program to further tie the compensation of our named executive officers to stockholder value. Aon assisted the compensation and HR committee with identifying a peer group specifically for purposes of the rTSR measurement goal related to the PSUs granted in 2021, or the 2021 rTSR PSUs, which group differed from the peer group selected for the 2020 rTSR PSUs. At the time they were designated, the peer group identified for the purposes of the 2021 rTSR PSUs consisted of commercial pharmaceutical and biotechnology companies that ranged between $750 million and $10 billion in market capitalization; Ironwood's market capitalization at that time was at the 39^th percentile relative to this custom peer group. Our compensation and HR committee then approved the following custom rTSR measurement peer group for the 2021 rTSR PSUs, which included all of our executive compensation peers with the exceptions of Akcea Therapeutics, Inc., which was acquired, and Horizon Therapeutics plc, which had exceeded the market capitalization range at the time the 2021 rTSR PSU peer group was designated:

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ACADIA Pharmaceuticals, Inc.		Jazz Pharmaceuticals plc
Acceleron Pharma Inc.		Karyopharm Therapeutics Inc.
Agios Pharmaceuticals, Inc.		Kronos Bio, Inc.
Alkermes plc		Ligand Pharmaceuticals Incorporated
Amarin Corporation plc		MannKind Corporation
Amicus Therapeutics, Inc.		MiMedx Group, Inc.
Amphastar Pharmaceuticals, Inc.		Neurocrine Biosciences, Inc.
Biohaven Pharmaceutical Holding Company Ltd.		Ocular Therapeutix, Inc.
bluebird bio, Inc.		Omeros Corporation
Blueprint Medicines Corporation		OPKO Health, Inc.
Coherus BioSciences, Inc.		Pacira BioSciences, Inc.
Corcept Therapeutics Incorporated		Perrigo Company plc
Deciphera Pharmaceuticals, Inc.		Prestige Consumer Healthcare Inc.
Emergent BioSolutions Inc.		PTC Therapeutics, Inc.
Endo International plc		Radius Health, Inc.
Epizyme, Inc.		Revance Therapeutics, Inc.
Esperion Therapeutics, Inc.		Sage Therapeutics, Inc.
Exelixis, Inc.		Sorrento Therapeutics, Inc.
Global Blood Therapeutics, Inc.		Supernus Pharmaceuticals, Inc.
GW Pharmaceuticals plc		Taro Pharmaceutical Industries Ltd.
Halozyme Therapeutics, Inc.		Theravance Biopharma, Inc.
Harmony Biosciences Holdings, Inc.		United Therapeutics Corporation
Heron Therapeutics, Inc.		Veracyte, Inc.
Insmed Incorporated		Vericel Corporation
Intercept Pharmaceuticals, Inc.		Viela Bio, Inc.
Ionis Pharmaceuticals, Inc.		Zogenix, Inc.
​	​	​

In February 2020. In addition,2021, our named executive officers (other than Mr. Mallon) were granted RSUs and, in March 2021, our named executive officers (other than Mr. Mallon) were granted PSUs, in each case under our 2019 Plan. Unlike the RSUs granted in 2020, which vest in equal installments over three years to facilitate thea transition in 2020 away from stock options that vested on a monthly to PSUs that are generally subject to two or three year cliff-based vesting, 2020 RSU grants to our named executive officersbasis, RSUs granted in 2021 vest as to approximately 33%25% of the underlying shares on each approximate anniversary of the grant date.date of the award, which is the vesting schedule typically used for RSU awards granted to employees. As stated previously, the 2021 PSU awards are subject to a single rTSR performance goal, which is measured over a three-year performance period ending December 31, 2023.

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The RSU and PSUs granted to our named executive officers (other than Mr. Mallon) in February and March of 2021, respectively, were as follows:

Named Executive Officer			2021 Annual PSU Grant (# of Shares of Class A common stock Subject to PSUs) (at target)			2021 Annual RSU Grant (# of Shares of Class A common stock Subject to RSUs)
​	​	​	​	​	​	​	​
Gina Consylman		​	84,541		​	84,951
Thomas McCourt			144,927			145,631
Jason Rickard		​	84,541		​	84,951
Michael Shetzline, M.D., Ph.D.			57,971			58,252
​	​	​	​	​	​	​	​

In making its determinations with respect to the size of equity awards awarded to each of our named executive officers, our compensation and HR committee took into account peer group and other market data from the Aon competitive assessment discussed below, as well as other factors including each executive's current equity holdings, expected future contributions and retention. Mr. Mallon did not receive equity awards in 2021 because he had provided notice of his intent to resign from the company at the time annual equity awards were granted.

Executive Severance Agreements and Benefits in the Event of a Change of Control

SeveranceThe severance arrangements that we have with our named executive officers, as well as other benefits provided in the event of a change of control, are described elsewhere in this proxy statement under the captioncaptions Named Executive Officer Severance Arrangements.Arrangements and Benefits in the Event of a Change of Control and Potential Payments Upon Termination or Change of Control. Severance benefits are only payable if the named executive officer has complied with all of our rules and policies, has executed a separation agreement that includes a release of claims and complies with his or her post-employment nondisclosure, noncompetition and nonsolicitationnon-solicitation obligations. We believe that offering these payments and benefits assists us in recruiting, retaining and motivating executive officers, facilitates the operation of our business, allows our named executive officers to better focus their time, attention and capabilities on our business, and provides for a clear and consistent approach to managing departures with mutually understood separation benefits. A further description of the severance arrangements is set forth elsewhere in this proxy statement under the captionsPost-Employment Arrangements,Named Executive Officer Severance Arrangements andPotential Payments Upon Termination or Change of Control.

Other Compensation

We maintain broad-based benefits, that are provided to all employees, including health insurance, life and disability insurance, dental insurance, fitness and transportation stipends, and a 401(k) plan with a 75% matching company contribution on the first $8,000 of an employee's annual contribution.contribution, which are provided to all employees.

We also maintain a relocation program under which we make certain benefits available to newly hired and existing employees, including our named executive officers, who are relocating to accept a new position with the company. Our relocation program covers reasonable expenses associated with the move and certain relocation services, including, as applicable, temporary housing assistance payments and a lump-sum relocation allowance, departure home sale assistance, rental assistance, new home search assistance, home purchase assistance, moving of household goods and vehicles assistance, and reimbursement of final trip expenses to the new area. We also provide tax assistance to our relocating employees to cover the costs associated with certain non-deductible relocation expenses, as we believe that this benefit is important to our ability to attract employees. Under our relocation program, participants are required to pay back the full amount of all relocation reimbursements in the event that they voluntarily terminate their employment or are terminated for "cause" within 12 months following the payment datespecified repayment periods.

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2021  Proxy Statement    43

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Table of their last relocation reimbursement.Contents

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​

Other than our broad-based benefits, or as otherwise described herein, none of our named executive officers receive perquisites of any nature.

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2020  Proxy Statement    41

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Post-Employment ArrangementsChief Executive Officer Transition

Effective March 12, 2021, Mr. Mallon resigned from his position as our chief executive officer and a member of our board of directors to pursue another opportunity. Mr. Mallon did not receive severance in connection with the termination of his employment. In February 2019,addition, Mr. Mallon forfeited 282,231 options, 354,796 RSUs and 221,061 PSUs in connection with his resignation.

In connection with his appointment as interim chief executive officer effective upon Mr. Mallon's resignation, our compensation and HR committee amendedrecommended and restated Ms. Gilbert's severance agreementour board determined to among other things, provide Ms. Gilbert the rightincrease Mr. McCourt's annual base salary from $573,200 to resign for any reason by February 2020,$775,000 and to have that resignation be treatedincrease Mr. McCourt's annual cash incentive bonus target from 60% (of $573,200) to 75% (of $775,000). The increase in annual base salary and annual cash incentive bonus target was intended to align Mr. McCourt's compensation for his service as our interim chief executive officer with Mr. Mallon's compensation as our chief executive officer. Mr. McCourt's increased salary and annual cash incentive bonus target will remain in place for a "good reason" terminationminimum of six months and for purposesso long as Mr. McCourt is serving as our interim chief executive officer. Mr. McCourt's severance arrangements and benefits in the event of her severance and other entitlements under her severance agreement. Ms. Gilbert resigned from the company effective February 28, 2020. For a descriptionchange of the payments and other benefits Ms. Gilbert receivedcontrol did not change in connection with herhis appointment as interim chief executive officer. In making its recommendations to the board relating to these compensation changes for Mr. McCourt's service as our interim chief executive officer, the compensation and HR committee considered competitive market practice and a desire to recognize Mr. McCourt for his willingness to assume the interim chief executive officer role and the increased responsibility associated with such role.

2021 Retention Awards

In light of Mr. Mallon's resignation seeas the company's chief executive officer in March 2021, in an effort to promote business continuity, our compensation and HR committee approved a cash retention bonus and an RSU retention award to our other four named executive officers who remained employed with the company on the date of the grant. Cash retention bonuses were valued at 50% of the named executive officer's 2021 base salary, and RSU awards were valued at 33% of each executive officer's 2021 annual equity target. In establishing the size of these grants, Aon presented market data and assisted our compensation and HR committee with approximating the value that another organization could potentially offer as a sign-on grant to recruit our executive talent relative to the current, unvested Ironwood equity held by our named executive officers.

Cash retention bonuses were awarded in the following amounts: Mr. McCourt (whose cash and RSU retention grants were made in his capacity as president, and not as interim chief executive officer) received a cash retention bonus of $286,600, Ms. Consylman received a cash retention bonus of $254,700, Mr. Rickard received a cash retention bonus of $242,100 and Dr. Shetzline received a cash retention bonus of $242,000. The cash retention bonuses are payable in two equal payments with 50% of the cash retention bonus paid in September 2021 and 50% of the cash retention bonus paid in June 2022, subject to the officer remaining an employee of the company in good standing on each payment date. Each executive also will receive both payments in the event of an involuntary termination of employment prior to June 1, 2022.

RSU retention awards were made in the following amounts: Mr. McCourt received 96,638 RSUs, Ms. Consylman received 56,372 RSUs, Mr. Rickard received 56,372 RSUs and Dr. Shetzline received 38,665 RSUs. The RSU retention awards are subject to provisions relating to the acceleration of time-based equity awards under each executive officers' severance agreement, as described elsewhere in this proxy statement under the captions Named Executive Officer Severance ArrangementsAgreements and Benefits in the Event of a Change of Control andPotential Payments Upon Termination or Change of Control elsewhere in this proxy statement..

In February 2020, the company entered into a consulting agreement with Ms. Gilbert under which Ms. Gilbert agreed to advise the company on various corporate development projects and governance matters. The agreement has a term of three months from the effective date, unless earlier terminated pursuant to its terms, and the company will pay Ms. Gilbert $90,000 for her services under the agreement.

Compensation of Named Executive Officers Who Transitioned to Cyclerion

Two of our 2019 named executive officers, Peter Hecht and Mark Currie, became Cyclerion employees in April 2019 in connection with the Separation. Prior to their transition from Ironwood to Cyclerion, the compensation and HR committee made decisions relating to Drs. Hecht and Currie's compensation in line with those made for the other named executive officers, including as described below under the captionCompensation Determination Process and elsewhere in thisCompensation Discussion and Analysis.

In January 2019, our compensation and HR committee reviewed and approved a base salary of $100,000 for Dr. Hecht, which amount was unchanged from his 2018 base salary. Dr. Hecht consistently declined increases in his base salary and he continued to earn the salary of $100,000 per year that he was first awarded in 1998. The compensation and HR committee also reviewed and approved Dr. Currie's base salary and provided him with a $15,000 increase in base salary from $485,000 to $500,000. Because they were only employed by Ironwood through March 2019, actual base salaries paid to Drs. Hecht and Currie for 2019 were $25,000 and $125,000, respectively.

In January 2019, our compensation and HR committee also awarded 1,000,000 stock options to Dr. Hecht and 600,000 stock options to Dr. Currie, which options vested as to 1/48th of the underlying shares on each monthly anniversary of the vesting commencement date until fully vested. On the date of grant, the stock options had an exercise price of $12.90 per share (the closing price of our Class A common stock on the Nasdaq Global Select Market on the grant date). For a description of the impact of the Separation on the number and the exercise price of stock options awarded to Drs. Hecht and Currie in January 2019, please seeEquity Impact of the Separation and the footnotes to theGrants of Plan-Based Awards table elsewhere in this proxy statement.

For 2019, Dr. Hecht's bonus, with an individual bonus target of 50% of his base salary, was to be determined primarily based on the achievement of our corporate goals. Dr. Currie had an individual bonus target of 50% of his base salary, 70% of which was tied solely to the achievement of our corporate goals for 2019 and 30% of which was tied to the achievement of corporate and individual performance goals (though our compensation and HR committee did not assess Dr. Currie's achievement of his individual goals in 2019 because of Dr. Currie's anticipated transition to Cyclerion). Neither Dr. Hecht nor Dr. Currie received a cash bonus for 2019 performance because they were not employed by Ironwood on the date in 2020 that cash bonuses for 2019 performance were paid. Further, the Separation did not trigger payments under Drs. Hecht and Currie's respective severance agreements with the company.

In connection with the Separation, Dr. Currie joined our board of directors on April 1, 2019. Upon joining our board of directors, Dr. Currie received a restricted stock grant of 2,995 shares of our Class A common stock for his service on our board of directors between April 1, 2019 and the 2019 annual meeting of stockholders pursuant to our 2014 Director Compensation Plan. In May 2019, Dr. Currie then received a restricted stock grant of 22,706 shares of our Class A common stock pursuant to our 2019 Director Compensation Policy for service on our board of directors from the date of our 2019 annual meeting of stockholders to the date of our 2020 annual meeting of stockholders. Dr. Currie also received a cash retainer of $37,500 for his service on our board of directors from April 1, 2019 through December 31, 2019. Compensation for Dr. Currie's service on our board of directors in 2019 following the Separation, as well as his

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compensation for services as an Ironwood employee in 2019 prior to the Separation, are included in theSummary Compensation Table, below.

Additional information on the basis for compensation decisions in 2019 relating to Drs. Hecht and Currie is available elsewhere in this proxy statement under the captionsRole of the Compensation and Human Resources Committee andRole of the Compensation Consultant: Benchmarking and Peer Group Analysis.

Equity Impact of the Separation

The employee matters agreement executed in connection with the Separation provided that outstanding Ironwood equity awards held by Ironwood and Cyclerion employees, including equity grants made in 2019 prior to the Separation to our 2019 named executive officers, were adjusted in accordance with the following principles:

•

For each award, the intent was to maintain, immediately following the distribution date, the economic value of the award immediately before the distribution date.



•

For both Cyclerion and Ironwood employees, except as noted below, vested Ironwood equity awards were converted into equity awards of both Ironwood and Cyclerion using the "basket approach" (as described below).



•

For Cyclerion employees, except as noted below, unvested Ironwood equity awards were converted into Cyclerion equity awards using the "concentration approach" (as described below).



•

For Ironwood employees, unvested Ironwood equity awards remained as Ironwood equity awards using the "concentration approach."



•

For non-employee directors of Cyclerion who had been non-employee directors of Ironwood, unvested Ironwood restricted stock were converted into unvested Cyclerion restricted stock using the "concentration approach."



•

For non-employee directors of Ironwood who remained non-employee directors of Ironwood, unvested Ironwood restricted stock continued as unvested Ironwood restricted stock, adjusted using the "concentration approach."



•

To the extent any adjustments to outstanding equity awards resulted in fractional interests in shares, the fractional interests were rounded down to the nearest whole share and Ironwood or Cyclerion, as the case may be, made cash payments to its respective employees in lieu of such fractional interests.

Basket Approach

Following the distribution, the number of shares underlying converted Cyclerion equity awards (whether held by Ironwood or Cyclerion employees) was determined according to a fixed ratio of one share of Cyclerion common stock for every 10 shares of Ironwood Class A common stock. The exercise price associated with converted Cyclerion equity awards (whether held by Ironwood or Cyclerion employees) was determined according to formulas based on the 10 day volume weighted average trading price of Ironwood Class A common stock for the 10 days immediately preceding the distribution and the purchase price of $175.0 million for Cyclerion common stock paid in a private placement Cyclerion executed in connection with the distribution.

Concentration Approach

Following the distribution, the number of shares underlying converted Cyclerion equity awards and any associated exercise prices was determined according to formulas based on the 10 day volume weighted average trading price of Ironwood Class A common stock for the 10 days immediately preceding the distribution and the purchase price of Cyclerion common stock paid in the private placement referenced above.

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2020  Proxy Statement    43

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The following table containsExecutive Officer Stock Ownership Guidelines

Following a summarycompetitive assessment of market data related to executive officer stock ownership requirements provided by Aon and guidance published by Investor Advisory Service, in October 2020, our compensation and HR committee recommended and, in December 2020, our board approved, Executive Officer Stock Ownership Guidelines. We believe our Executive Officer Stock Ownership Guidelines further align the interests of our executive officers with those of our stockholders and also incentivize executive officers to focus on maximizing long-term value.

Our Executive Officer Stock Ownership Guidelines, which apply to each of our executive officers as defined in the Exchange Act, provide that our chief executive officer is required to hold shares of the treatmentCompany's Class A common stock with a value equal to at least four (4) times his or her annual base salary and that other executive officers are required to hold shares of each typethe Company's Class A common stock with a value equal to one (1) times his or her annual base salary. Executive officers are required to achieve the applicable level of Ironwood equity award inownership by the Separation:

​	​	​	​	​
Typelater of December 2025 (five years from the date of adoption of the Executive Officer Stock Ownership Guidelines) or the fifth anniversary of the date a person was initially designated as an executive officer of the Company. Shares that count towards satisfaction of the Executive Officer Stock Ownership Guidelines include, among other forms of ownership, shares held outright by the executive officer or a member of his or her immediate family and the in-the-money value of Ironwood Award		Cyclerion Employees		Ironwood Employees
​	​	​	​	​
Vested Stock Options (other than Vested Incentive Stock Options granted under the Ironwood 2010 Incentive Plan)		Continued to hold vested Ironwood stock options and certain other vested and received a pro rata portion of vested stock options of Cyclerion, each as equitably adjusted to reflect the distribution		Continued to hold vested Ironwood stock options and received a pro rata portion of vested stock options of Cyclerion, each as equitably adjusted to reflect the distribution
​	​	​	​	​
Vested Incentive Stock Options granted under the Ironwood 2010 Incentive Plan		Substituted with vested Cyclerion incentive stock options, unless employee elected to convert to non-qualified stock options of both Ironwood and Cyclerion, each as equitably adjusted to reflect the distribution		Continued to hold vested Ironwood incentive stock options, unless employee elected to convert to non-qualified stock options of both Ironwood and Cyclerion, each as equitably adjusted to reflect the distribution
​	​	​	​	​
Unvested Stock Options		Substitute with unvested Cyclerion stock options of comparable value		Continue to hold unvested Ironwood stock options, as equitably adjusted to reflect the distribution
​	​	​	​	​
Restricted Stock Units (other than July 2018 Recognition Restricted Stock Units)		Substituted with Cyclerion restricted stock units of comparable value		Continued to hold Ironwood restricted stock units, as equitably adjusted to reflect the distribution
​	​	​	​	​
July 2018 Recognition Restricted Stock Units		Continued to hold Ironwood restricted stock units, as equitably adjusted to reflect the distribution		Continued to hold Ironwood restricted stock units, as equitably adjusted to reflect the distribution
​	​	​	​	​

Each Ironwood equity award that was converted into a Cyclerion equity award is subject to substantially the same terms and vesting conditions as were applicable to the Ironwood equity awards prior to(other than unearned performance-based awards), net of applicable taxes and the distribution. Please seeOutstanding Equity Awards at Fiscal Year-End—Ironwood Equity Awards at Fiscal Year-End andOutstanding Equity Awards at Fiscal Year-End—Cyclerion Equity Awards at Fiscal Year-End for detailed informationexercise price (if applicable).

Compliance with the stock ownership requirements will be measured on the impactdate of the Separationannual meeting of stockholders of the company each year based on the annualized salary then in effect for each officer. Failure to comply with the Executive Officer Stock Ownership Guidelines will (among other things, as may be determined by the compensation and HR committee) require executive officers to retain at least 100% of the shares, net of applicable tax withholding and the payment of any exercise or purchase price (if applicable), received upon the vesting or settlement of equity awards held by our 2019 named executive officers, including equity grants made in 2019 prior toor the Separation.exercise of stock options.

Basis for Our Compensation Policies and Decisions

Our Values and Goals

The objective of our compensation policies is to provide compensation and incentives that align employee actions and motivations with the interests of our stockholders; attract, retain, motivate and reward outstanding talent across Ironwood through well-communicated programs that are aligned with our vision and mission; and support a positive company culture.

We are guided by the following principles with respect to our compensation determinations:

•

design compensation and incentive programs that align employee actions and motivations with the interests of our stockholders, support our business objectives and hold employees accountable for the achievement of key goals and milestones;



•

foster and support our performance-driven culture by setting clear, aggressive, high value goals, rewarding outstanding performers to the extent these goals are achieved, and making sure our best performers know clearly that we value their contributions;



•

as with all spending, serve as careful stewards of our stockholders' assets when making compensation decisions;

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•

maximize our employees' sense of ownership so that they have a long-term owner's perspective, can see the impact of their efforts on our success, and can share in the benefits of that success through the opportunity to become stockholders of Ironwood through equity-based awards;



•

recognize that compensation is one of a number of tools to stimulate and reward productivity, great drug development, and successful commercialization, together with recognizing individual growth potential, providing a great workplace culture, and sharing in our success;



•

foster a strong team culture, focused on our principles of great drug development and commercialization, which is reinforced through our compensation and incentive programs;



•

design compensation and incentive programs that are fair, equitable and competitive; and



•

design compensation and incentive programs that are simple and understandable.

Executive Compensation Governance

Highlighted procedures and tools that we use to ensure effective governance of compensation plans and decisions include:

•

our compensation and HR committee has the authority to hire independent counsel, compensation consultants and other advisors;



•

our compensation and HR committee conducts a regular review and assessment of risk as it relates to our compensation policies and practices;



•

as part of our insider trading prevention policy, our executive officers and directors are prohibited from engaging in any hedging or monetization transactions ofwith respect to our Class A common stock, including through the use of financial instruments such as prepaid variable forwards, equity swaps, collars and exchange funds;



•

we have no perquisites other than broad-based benefits, including health and welfare benefits, transportation and fitness stipends, a 401(k) plan and a relocation program that we make available to all of our employees; under our relocation program, participants are required to pay back the full amount of all relocation benefits in connection with their departure from Ironwood in certain circumstances;



•

our executive severance agreements (i) do not provide for tax gross-ups and (ii) contain double-trigger requirements for equity acceleration and other benefits in the event of a change of control;



•

sevennine of our nineten directors are independent, including all members of our compensation and HR committee, and we have instituted stock ownership guidelines that will require directors to accumulate and continuously hold a specified amount of our Class A common stock (seeDirector Stock Ownership Guidelines elsewhere in this proxy statement for additional information); and



•

we have instituted executive stock ownership guidelines that will require executive officers to accumulate and continuously hold a specified amount of our Class A common stock (see Executive Officer Stock Ownership Guidelines elsewhere in early 2019, this proxy statement for additional information); and



•

we adoptedhave a clawback policy that provides our board of directors, in the event of a financial restatement due to material noncompliance with financial reporting requirements and where an executive engaged in intentional misconduct that caused or partially caused the need for the restatement, with the discretionary right to recover from our current and former executive officers that portion of the bonus or other incentive compensation that was received by the covered executives or effect the cancellation of unvested and vested equity awards previously granted to the covered executives based on our financial performance results and that would not have been awarded based on the restated results. The board of

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directors' recovery rights under this policy will be without prejudice to other remedies the company may have for the recovery or adjustment of incentive compensation. Additionally, if we are required to restate our financial results due to our material noncompliance with any financial reporting requirements under the federal securities laws as a result of misconduct, our chief executive officer and chief financial officer may be legally required to reimburse us for any bonus or other incentive-based or equity-based compensation they receive in accordance with the provisions of section 304 of the Sarbanes-Oxley Act of 2002.

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Compensation Determination Process

Our compensation policies are evaluated annually, andHistorically, our compensation and HR committee takeshas determined our corporate performance for the prior year and also approved the compensation of all executive officers, including our chief executive officer. In December 2020, the board approved updates to our corporate governance guidelines and the charter of the compensation and HR committee to provide that, beginning in 2021, (i) our board would assess the Company's corporate performance and (ii) our compensation and HR committee would recommend, and our board would approve, the compensation determination for our chief executive officer. In determining the compensation of our chief executive officer, the board deliberates and votes on the chief executive officer's compensation outside of the presence of the chief executive officer, and the chief executive officer and any other non-independent directors abstain from such determination. Our compensation and HR committee and board similarly followed this process in 2021 in determining compensation for Mr. McCourt that specifically related to his service as our interim chief executive officer.

In January 2021, our board met and, following the recusal of non-independent directors, our board approved our corporate goal achievement for 2020. Following the board's corporate goal assessment, our compensation and HR committee evaluated the performance of our executive officers (other than Mr. Mallon), including performance against goals and objectives relevant to such executive officers' compensation, and then approved salary increases, cash bonuses and equity awards for our executive officers (other than Mr. Mallon). The compensation and HR committee similarly evaluated Mr. Mallon's performance and made a recommendation to the board relating to Mr. Mallon's bonus for 2020 performance; the compensation and HR committee did not make a recommendation as to go forward compensation for Mr. Mallon as Mr. Mallon had indicated his intent to resign at the time compensation decisions were made. In making these compensation-related decisions or recommendations for 2020 performance, our compensation and HR committee considered the competitive assessment prepared by Aon, as described in more detail below, as well as the other factors described in this Compensation Discussion and Analysis.

At its meeting in March 2021, following the recusal of non-independent directors, the board voted on Mr. Mallon's 2020 bonus; Mr. Mallon was not present for the board's deliberation on his 2020 bonus.

The compensation and HR committee also approves our bonus pool, which is calibrated based on corporate performance, and our equity pools, which are calibrated for competitive market practice, and assigns a portion of each of these pools to all of our employees other than our executive officers. Prior to Mr. Mallon's resignation, the compensation and HR committee delegated allocation of these portions to an RSU committee, which was comprised only of Mr. Mallon; following Mr. Mallon's resignation, allocation decisions will be made by members of senior management designated by our compensation and HR committee.

Our compensation and HR committee also evaluates our compensation policies annually, taking into consideration our results of operations, our long and short-term goals, individual goals, market data, the competitive market for our executive officers and general economic factors when making individualfactors. Additionally, our compensation and HR committee or board (in the case of the determinations relating to chief executive officer compensation) may recommend or decide, as appropriate, to modify the mix or amount of base salary, bonus, and long-term incentives to best fit an executive

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officer's specific circumstances or, if warranted by competitive market conditions, to attract, retain and motivate skilled personnel. For example, our compensation and HR committee may recommend or decide, and our board may decide with respect to our namedchief executive officers. officer, to grant additional equity awards to an executive officer if that officer receives a base salary or cash bonus award significantly below that of his or her counterparts in our peer group, despite successful attainment of our corporate goals or his or her individual goals. We believe that this discretion and flexibility allows our compensation and HR committee and board (in the case of determinations of our chief executive officer's compensation) to better achieve our compensation objectives.

Role of the Compensation and HR Committee

As set forth in our compensation and HR committee'sits written charter, our compensation and HR committee has the responsibility for evaluating the performance of our executive officers, taking into account the determination of our board with respect to our corporate performance; reviewing and approving the compensation of our executive officers; annuallyofficers (other than our chief executive officer); reviewing and determiningrecommending to the board our chief executive officer's compensation based on the committee's evaluation of his performance;compensation; recommending to the full board of directors the adoption of new compensation plans; administering our existing plans; reviewing and recommending director and committee compensation to the full board of directors;board; reviewing and overseeing our Executive Officer Stock Ownership Guidelines; overseeing succession planning for our senior management; and reviewing risks associated with our compensation policies and practices. In addition, our compensation and HR committee is responsible for ensuring that our compensation policies are aligned with our compensation philosophy and guiding principles.

Early each year, our compensation and HR committee finalizes its assessment of our corporate performance for the prior year. Upon completion of such goal assessment, our bonus and equity pools are calibrated for corporate performance and approved by our compensation and HR committee. Our compensation and HR committee assigns a portion of each of these pools to all of our employees other than our executive officers, and delegates the allocation of these portions to our chief executive officer and our chief financial officer. Our compensation and HR committee also approves any salary increase, cash bonus and equity awards for our chief executive officer and, in consultation with our chief executive officer, for each of our other executive officers. In making these compensation-related decisions for 2019 performance, our compensation and HR committee considered the competitive assessment prepared by Pearl Meyer, and described in more detail below, as well as the other factors described in thisCompensation Discussion and Analysis.

Additionally, our compensation and HR committee may decide, as appropriate, to modify the mix or amount of base salary, bonus, and long-term incentives to best fit an executive officer's specific circumstances or, if required by competitive market conditions, to attract, retain and motivate skilled personnel. For example, our compensation and HR committee may decide to grant additional equity awards to an executive officer if that officer receives a base salary or cash bonus award significantly below that of his or her counterparts in our peer group, despite successful attainment of our corporate or his or her individual goals. We believe that this discretion and flexibility allows our compensation and HR committee to better achieve our compensation objectives.

Role of the Compensation and Human Resources Committee

In 2019,2020, our compensation and HR committee made all of the compensation determinations with respect to each of our 20192020 named executive officers. In making its determinations with respectofficers, including ratifying and approving compensation paid or awarded to Mr. Rickard and Dr. Hecht,Shetzline prior to their designation as executive officers of the company in April 2020. As described above, beginning in 2021, our compensation and HR committee took into account the feedback from members ofrecommended, and our board approved, compensation determinations for Mr. Mallon, including compensation determinations made in recognition of directors,performance in 2020, as well as the feedback from eachcompensation determinations for Mr. McCourt in 2021 in respect of his service as our otherinterim chief executive officers, and a number of other members of our management team. In developing Mr. Mallon's initial compensation package, our compensation and HR committee endeavored to compensate Mr. Mallon, in part, for the outstanding equity that he forfeited by leaving his previous employer. The compensation and HR committee also took into account the factors listed in the following paragraph in determining Mr. Mallon's initial compensation package. officer.

In making its determinations with respect to each of our named executive officers other(other than Dr. Hecht and Mr. Mallon,Mallon) relating to compensation for performance in 2020, our compensation and HR committee took into account the feedback and recommendations from Dr. Hecht in the first quarter of 2019 and from Mr. Mallon, for the remainder of 2019, as well as from the named executive officer's direct reports and other members of our management team.

The components of each of our named executive officer's including Mr. Mallon's, initial compensation package was based on numerous factors, including:

•

the individual's particular background and circumstances, including prior relevant work experience and compensation paid prior to joining us;



•

the individual's role with us and the compensation paid to similar persons in the companies represented in the compensation data that our compensation and HR committee reviewed;

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•

the demand for people with the individual's specific expertise and experience at the time of hire;



•

performance goals and other expectations for the position;



•

comparison to other executive officers within Ironwood having similar levels of expertise and experience; and



•

uniqueness of industry skills.

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Role of the Compensation Consultant: Benchmarking and Peer Group Analysis

Our compensation and HR committee has the authority to select and retain independent advisors and consultants to assist it with carrying out its responsibilities, and we are required to pay any related expenses approved by the committee. In 2019,2020, our compensation and HR committee exercised such authority and engaged Aon as its authority to engage Pearl Meyer as a compensation consultant from January through July and Aon from August through December. Each of Pearl Meyer andconsultant. Aon reported directly to our compensation and HR committee duringthroughout the period of its engagement. Pearl MeyerOther than the purchase of certain benefits surveys and employee compensation benchmarking data from Aon in 2020 and certain other accounting and consulting services related to equity plan matters, including forfeiture rate analysis, PSU award design and 2020 rTSR PSU valuation, Aon did not provide us with any services in 20192020 other than those requested by our compensation and HR committee. Prior to its engagement as compensation consultant beginning in August 2019, Aon provided us with certain services in 2019 related tocommittee and the equity impactreview of the Separation. In addition, following its engagement as compensation consultant, we purchased certain benefits surveys and employee compensation benchmarking data from Aon. Aon also reviewed thisCompensation Discussion and Analysis for conformance with best practices. Based on the scope of our compensation and HR committee's engagements with Pearl Meyer and Aon, it was determined that neither Pearl Meyer nor Aon haddid not have a conflict of interest in their respective rolesits role as compensation consultant under applicable rules for the period of their engagements.rules.

In order to assist our compensation and HR committee in setting 2020 and 2021 compensation, respectively, Aon conducted competitive assessments of 2019 compensation, Pearl Meyer conducted a competitive assessment of 2018and 2020 target compensation for our named executive officers, with a focus on the following components of our named executive officer compensation:

•

base salary;



•

target total cash compensation (which is base salary plus the target bonus);



•

long-term equity incentives (which are valued based on grant date fair value); and



•

target total direct compensation (which is target total cash compensation plus the value of the most recent long-term incentive grant).

In conducting this assessment, Pearl MeyerAon analyzed the components of our named executive officer compensation listed above, in each case measured against our peer group at the time, recognizing that such peer group companies tended to be larger than us (including with respect to revenues). The peer group that was in place for this assessment was composed of the following 15 companies, which at the time25^th, 50^th and 75^th percentiles of our review had a median market capitalization of approximately $3.0 billion, a median of approximately 540 employees, and a commercial drug or drug candidate in later stage development:

Acorda Therapeutics, Inc.		Intercept Pharmaceuticals, Inc.
Agios Pharmaceuticals, Inc.		Ionis Pharmaceuticals
Alkermes plc		Nektar Therapeutics
Alnylam Pharmaceuticals, Inc.		Pacira Pharmaceuticals
AMAG Pharmaceuticals, Inc.		Serepta Therapeutics
Corcept Therapeutics		Tesaro, Inc.
Horizon Pharma plc		United Therapeutics Corporation
ImmunoGen
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In assisting ourexecutive compensation and HR committee in setting 2019 compensation, Pearl Meyer also presented proxy data from the Radford Global Life Sciences Survey, which was comprised of companies that represent a broader market perspective and similar employee population to us, and a Market Composite, which combined the peer group data and Radford Global Life Sciences Survey data by weighting each source equally. Although this competitive assessment was not used to mandate any specific compensation decisions, our compensation and HR committee considered the results of this assessment when making base salary, cash bonus and long-term equity incentive award determinations with respect to our named executive officers in early 2019.

group. Our peer group is reviewed at least annually by our compensation and HR committee. In setting our peer group, our compensation and HR committee applies a qualitative lens to help focus the group on the companies with which we are competing for talent. Our compensation and HR committee first identifies a potential pool of peer companies from a number of sources, including the companies listing Ironwood in their peer groups and the other companies listed in such peer companies' peer groups, as well as companies included in third-partythird party peer group assessments. Our compensation and HR committee then considers certain size filters including market capitalization, revenue, and number of employees, as well as certain business model filters including commercial focus, and growth.

In July 2019, our The peer group that Aon proposed and that the compensation and HR committee approved a new peer group, which peer group Aon used as a reference point in advising ourconnection with 2020 compensation and HR committee regarding compensation decisions made beginning in the fourth quarter of 2019. This updated peer group is composed of the following 17 companies, which at the time ofthey were designated as our reviewpeer group had a median market capitalization of approximately $2.7

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$2.7 billion, median revenue of approximately $249 million, a median of 482 employees, and a commercial drug or drug candidate in later stage development:

ACADIA Pharmaceuticals, Inc.		Halozyme Therapeutics, Inc.
Agios Pharmaceuticals, Inc.		Horizon Therapeutics plc
Akcea Therapeutics, Inc.		Intercept Pharmaceuticals, Inc.
Alkermes plc		Pacira BioSciences, Inc.
Amicus Therapeutics, Inc.		PTC Therapeutics, Inc.
bluebird bio, Inc.		Radius Health, Inc.
Blueprint Medicines Corporation		Supernus Pharmaceuticals, Inc.
Coherus BioSciences, Inc.		United Therapeutics Corporation
Corcept Therapeutics Incorporated
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In assisting our compensation and HR committee in setting 2020 compensation, Aon also presented proxy peer data and results from the Radford Global Life Sciences Survey, which was comprised of companies that represent a broader market perspective and similar employee population to us, and a Market Composite, which combined the peer group data and Radford Global Life Sciences Survey data by weighting each source equally. Although this competitive assessment was not used to mandate any specific compensation decisions, our compensation and HR committee considered the results of this assessment when making base salary, cash bonus and long-term equity incentive award determinations with respect to our named executive officers in early 2020.

In October 2020, our compensation and HR committee re-approved the peer group listed above, which peer group the compensation and HR committee continued to use as a reference point in making decisions through the date of this proxy statement.

Tax and Accounting Considerations

While our compensation and HR committee generally considersmay consider the tax and accounting implications of its executive compensation decisions, neither element was a material consideration in the compensation awarded to our named executive officers in 2019.2020.

Executive Compensation Risk Assessment

Our compensation and HR committee engaged Aon to conduct a formal compensation risk assessment in December 2020. The compensation and HR committee then reviewed our 20192020 compensation policies as generally applicable to our employees and believesdetermined that our policies did not encourage excessive and unnecessary risk-taking, and that the level of risk that they did encourage was not reasonably likely to have a material adverse effect on Ironwood. Our compensation and HR committee considered the following, among other factors, in reviewing our compensation policies related to 20192020 compensation:

•

our use of different types of compensation vehicles provided a balance of long and short-term incentives with fixed and variable components;

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•

we granted equity-based awards with time-based vesting, which encouraged participants to look to long-term appreciation in equity values;



•

our annual bonus determinations for each employee were dependent on achievement of a diverse set of company-level goals, which we believe promoted long-term value; and



•

our system of internal control over financial reporting and code of business conduct and ethics, among other things, reduced the likelihood of manipulation of our financial performance to enhance payments under any of our incentive plans.

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Compensation Tables

Summary Compensation Table

The following table sets forth information regarding the compensation paid or accrued to, or earned by, each of our named executive officers during the years ended December 31, 2020, 2019 and 2018, and 2017.as applicable.

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Name and Principal Position*			Year			Salary ($)			Bonus ($)			Stock Awards ($)(1)			Option Awards ($)(1)(2)			Non-Equity Incentive Plan Compensation ($)(3)			All Other Compensation ($)(4)			Total ($)
​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​
Mark Mallon		​	2019		​	750,000		​	880,000	(5)	​	3,692,810	(6)	​	3,804,331	(7)	​	797,063		​	144,596		​	10,068,800
Chief Executive Officer		​	2018		​	—		​	—		​	—		​	—		​	—		​	—		​	—
​		​	2017		​	—		​	—		​	—		​	—		​	—		​	—		​	—
Gina Consylman			2019			480,000			250,000	(8)		1,467,731	(9)		888,546			358,800			8,502			3,453,579
Chief Financial Officer and			2018			415,000			—			782,385			501,764			207,500			8,040			1,914,688
Senior Vice President			2017			334,263			—			440,213			—			185,000			8,040			967,516
Halley E. Gilbert		​	2019		​	480,000		​	250,000	(8)	​	1,467,731	(9)	​	888,546		​	340,080		​	8,502		​	3,434,859
Former Chief Administrative Officer and		​	2018		​	460,000		​	—		​	740,610		​	463,722		​	230,000		​	33,425		​	1,927,757
Senior Vice President, Corporate Development		​	2017		​	440,000		​	​		​	670,800		​	619,728		​	195,000		​	8,040		​	1,933,568
Thomas A. McCourt			2019			511,250	(10)		—			1,760,143	(11)		2,370,159			454,272			8,502			5,104,326
President			2018			465,000			—			549,641			869,479			232,500			34,002			2,150,622
			2017			450,000			—			440,212			1,220,089			191,000			8,040			2,309,341
Peter M. Hecht, Ph.D.		​	2019		​	25,000	(12)	​	—		​	—		​	6,127,900		​	—		​	6,589		​	6,159,489
Former Chief Executive Officer		​	2018		​	100,000		​	1,192,500		​	—		​	3,842,268		​	—		​	25,348		​	5,160,116
​		​	2017		​	100,000		​	—		​	—		​	5,887,416		​	—		​	8,040		​	5,995,456
Mark G. Currie, Ph.D.			2019			125,000	(13)		—			286,306	(14)		3,676,740			—			44,088			4,132,134
Former Senior Vice President,			2018			485,000			—			231,360			1,424,289			242,500			62,271			2,445,420
Chief Scientific Officer and President of R&D			2017			470,000			—			—			1,936,650			210,000			8,040			2,624,690
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Name and Principal Position*			Year			Salary ($)(1)			Bonus ($)			Stock Awards ($)(2)			Option Awards ($)(2)			Non-Equity Incentive Plan Compensation ($)(3)			All Other Compensation ($)(4)			Total ($)
​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​
Mark Mallon*		​	2020		​	801,173		​	—		​	5,423,731		​	—		​	585,169		​	11,040		​	6,821,113
Former Chief Executive		​	2019		​	750,000		​	880,000		​	3,692,810		​	3,804,331		​	797,063		​	144,596		​	10,068,800
Officer		​	2018		​	—		​	—		​	—		​	—		​	—		​	—		​	—
Gina Consylman			2020			512,751			—			1,676,402			—			264,652			11,040			2,464,845
Chief Financial Officer and			2019			480,000			250,000			1,467,731			888,546			358,800			8,502			3,453,579
Senior Vice President			2018			415,000			—			782,385			501,764			207,500			8,040			1,914,688
Thomas McCourt*		​	2020		​	576,120		​	—		​	2,465,327		​	—		​	357,409		​	11,040		​	3,409,896
President and Interim		​	2019		​	511,250		​	—		​	1,760,143		​	2,370,159		​	454,272		​	8,502		​	5,104,327
Chief Executive Officer		​	2018		​	465,000		​	—		​	549,641		​	869,479		​	232,500		​	34,002		​	2,150,622
Jason Rickard			2020			473,314			—			1,479,191			—			258,338			11,040			2,221,883
Chief Operating Officer and			2019			—			—			—			—			—			—			—
Senior Vice President			2018			—			—			—			—			—			—			—
Michael Shetzline, M.D., Ph.D.		​	2020		​	464,681		​	100,000	(5)	​	1,121,001	(6)	​	—		​	194,558		​	11,040		​	1,891,310
Chief Medical Officer, Senior		​	2019		​	—		​	—		​	—		​	—		​	—		​	—		​	—
Vice President and Head of		​	2018		​	—		​	—		​	—		​	—		​	—		​	—		​	—
Drug Development Development		​			​			​			​			​			​			​			​
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*

Mr. Mallon joined the company in 2019. Ms. Gilbert was a named executive officer in 2017 but was not a named executive officer in 2018. Ms. Gilbert resigned from the company effective on March 12, 2021. In connection therewith, Mr. McCourt became the company's interim chief executive officer in February 2020. Drs. Hechtaddition to his role as the company's president.

(1)

Salaries reported for 2020 reflect amounts paid in 2020 (as opposed to annual base salary rates). Fiscal year 2020 included one more pay date than fiscal years 2019 and Currie transitioned to Cyclerion in April 2019 in connection with the Separation. Also in connection with the Separation in April 2019, Dr. Currie joined our board of directors.

2018.

(2)

(1)  For 2019,2020, reflects the fair value of time-based RSU RSAs, and stock optionPSU awards on the date of grant calculated in accordance with Financial Accounting Standards Board issued Accounting Standards Codification Topic 718,, Compensation—Stock Compensation, or ASC 718. For a discussion of the assumptions used in the valuation of awards made in 2019,2020, see Note 1514 to our consolidated financial statements for the year ended December 31, 20192020 included in our Annual Report on Form 10-K that we filed with the SEC on February 13, 2020.17, 2021. All values reported exclude the effects of potential forfeitures. Unless otherwise noted, reflectsamounts reported reflect the grant date fair value of RSUs and PSUs awarded in January 2019February 2020 in connection with annual equity awards.

(2)  Unless otherwise noted, reflects With respect to PSUs granted to the named executive officers in 2020, the aggregate grant date fair value was determined based on the probable outcome of the performance conditions associated with such awards (target) at the date of grant. Assuming the maximum level of performance (200%) is achieved, the aggregate grant date fair value of stock options awardedthe PSUs granted in January 2019 in connection with annual equity awards.

2020 is as follows: $5,586,210 for Mr. Mallon, $1,726,622 for Ms. Consylman, $2,539,182 for Mr. McCourt, $1,523,504 for Mr. Rickard, and $1,145,974 for Dr. Shetzline.

(3)

(3)  Consists of payments made under our annual cash bonus program in 2020 for performance in 2019, as describedthe relevant year. For a description of bonuses paid in 2021 for performance in 2020, see the disclosure included elsewhere in this proxy statement under the captionCash Bonus.

(4)

For each executive officer, for 2020, $6,000 of such amount consists of matching contributions made under our 401(k) plan, as well as an amountand the remainder is attributable to a transportation stipend and a fitness stipend. For Mr. Mallon, such amount includes $99,036 that he received for relocation expenses pursuant to his new hire arrangement and intended to facilitate his transition to

(5)

Reflects payment of the Boston, Massachusetts area, as well as $37,137 that he received during the year for reimbursementsecond installment of taxes owed on this relocation allowance. For Dr. Currie, such amount includes $37,500 for his service on our board of directors from April 1, 2019 through December 31, 2019.

(5)  Reflects theShetzline's sign-on bonus, which was paid to Mr. Mallon in January 2019early 2020 in connectionaccordance with the commencementterms of his employment in January 2019.

offer.

(6)

Includes the aggregate grant date fair value of (a) 93,03628,135 RSUs and 28,135 PSUs awarded to Mr. MallonDr. Shetzline in January 2019February 2020 in connection with the commencement of his employment in January 2019annual equity awards and (b) 206,87320,740 RSUs and 20,740 PSUs awarded to Mr. MallonDr. Shetzline in April 20192020 as a recognition award in connection with his promotion to chiefdesignation as an executive officer upon completion of the Separation.

(7)  Includes the fair value of (a) 171,526 stock options awarded to Mr. Mallon in January 2019 in connection with the commencement of his employment in January 2019 and (b) 423,049 stock options awarded to Mr. Mallon in April 2019 in connection with his promotion to chief executive officer upon completion of the Separation.

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(8)  Reflects a special bonus awarded to Ms. Consylman and Ms. Gilbert in May 2019 in recognition of their significant contributions to and performance in connection with the Separation, and with respect to Ms. Gilbert, her expanded role overseeing our corporate development function.

(9)  Includes the fair value of (a) 72,500 RSUs awarded to each of Ms. Consylman and Ms. Gilbert in January 2019 in connection with annual equity awards and (b) 41,150 RSUs awarded to each of Ms. Consylman and Ms. Gilbert in December 2019 as a special retention award.

(10)  Reflects Mr. McCourt's pro-rated salary of $485,000 for the period January 1, 2019 through March 31, 2019 during which time he served as our senior vice president, marketing and sales, and chief commercial officer, and his pro-rated salary of $520,000 for the period April 1, 2019 through December 31, 2019 during which time he served as our president.

(11)  Includes the fair value of (a) 22,852 RSUs awarded to Mr. McCourt in May 2019 in connection with his promotion to president and (b) 115,220 RSUs awarded to Mr. McCourt in December 2019 as a special retention award.

(12)  Reflects the pro-rated portion of Dr. Hecht's $100,000 annual salary, which was paid for the period January 1, 2019 through March 31, 2019, during which he served as our chief executive officer.

(13)  Reflects the pro-rated portion of Dr. Currie's $500,000 annual salary, which was paid for the period January 1, 2019 through March 31, 2019, during which he served as our senior vice president, chief scientific officer and president of R&D.

(14)  Includes the fair value of (a) 2,995 RSAs awarded to Dr. Currie in April 2019 in connection with his service on our board of directors between April 1, 2019 and the 2019 annual meeting of stockholders and (b) 22,706 RSAs awarded to Dr. Currie in May 2019 in connection with his service on our board of directors from the date of our 2019 annual meeting of stockholders to the date of our 2020 annual meeting of stockholders.

Grants of Plan-Based Awards

The following table sets forth information regarding non-equity and equity awards granted to each of our named executive officers during the year ended December 31, 2019.2020. All non-equity incentive plan awards were made pursuant to our cash bonus program described in more detail elsewhere in this proxy statement under the captionCash Bonus.

We granted RSUs and stock option awardsPSUs to our named executive officers other than Mr. Mallon, in January 2019February 2020. We also granted Dr. Shetzline additional RSUs and PSUs in recognition of performance in 2018. In addition, we granted Mr. Mallon RSU and stock option awards in connection with the commencement of his employment with the company in January 2019 andApril 2020 in connection with his becoming chiefdesignation as an executive officer upon the completion of the Separation in April 2019. We also granted Mr. McCourt a stock option award in connection with his promotion to president upon the completion of the Separation in April 2019. In addition, Mses. Consylman and Gilbert and Mr. McCourt were granted special RSU retention awards in December 2019. We granted Dr. Currie RSAs in connection with his joining our board of directors upon completion of the Separation in April 2019 and for his service on our board of directors from the date of our 2019 annual meeting of stockholders to the date of our 2020 annual meeting of stockholders.company.

All RSUs and PSUs granted in 2019 represent2020 represented the right to receive shares of our Class A common stock all RSAs granted in 2019 are awardsupon the vesting of our Class A common stock that are subject to restrictions, and all stock options granted in 2019 consist of options to purchase shares of our Class A common stock with an exercise price equal to the fair market value of our Class A common stock on the date of grant. Equity awards granted in 2019 before our 2019 annual meeting of stockholders were granted under our 2010 Plan and equity awards granted in 2019 after our 2019 annual meeting of stockholders were granted under our 2019 Plan.such awards. The vesting schedule of each RSA, RSU and stock optionsuch award included in the following table is described in the footnotes to theIronwood Outstanding Equity Awards at Fiscal Year-End table.

Information presented

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Compensation and HR Committee Approval Date (if different than

Estimated Future Payouts Under Non- Equity Incentive Plan Awards(2)

Estimated Future Payouts Under Equity Incentive Plan Awards(3)(#)

All Other Stock Awards: Number of Shares of Stock or

Grant Date Fair Value of Stock

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Name

Grant Date

Grant Date)

Target ($)

Threshold

Target

Maximum

Units (#)(4)

Awards ($)(5)

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​

​

​

​

​

Mark Mallon

​

2/27/2020

​

2/20/2020

​

—

​

—

​

—

​

—

​

221,061

​

2,630,626

​

​

2/27/2020

​

2/20/2020

​

—

​

66,318

​

221,061

​

442,122

​

—

​

2,793,105

​

​

—

​

—

​

579,375

​

—

​

—

​

—

​

—

​

—

Gina Consylman

2/27/2020

2/20/2020

—

—

—

—

68,327

813,091

2/27/2020

2/20/2020

—

20,498

68,328

136,656

—

863,311

—

—

247,200

—

—

—

—

—

Thomas McCourt

​

2/27/2020

​

2/20/2020

​

—

​

—

​

—

​

—

​

100,482

​

1,195,736

​

​

2/27/2020

​

2/20/2020

​

—

​

30,145

​

100,482

​

200,964

​

—

​

1,269,591

​

​

—

​

—

​

333,840

​

—

​

—

​

—

​

—

​

—

Jason Rickard

2/27/2020

—

(1)

—

—

—

—

60,289

717,439

2/27/2020

—

(1)

—

18,087

60,289

120,578

—

761,752

—

—

228,375

—

—

—

—

—

Michael Shetzline,

​

2/27/2020

​

—

(1)

​

—

​

—

​

—

​

—

​

28,135

​

334,807

M.D., Ph.D.

​

2/27/2020

​

—

(1)

​

—

​

8,441

​

28,135

​

56,270

​

—

​

355,487

​

​

4/24/2020

(6)

​

4/18/2020

​

—

​

—

​

—

​

—

​

20,740

​

213,207

​

​

4/24/2020

(6)

​

4/18/2020

​

—

​

6,222

​

20,740

​

41,480

​

—

​

217,500

​

​

—

​

—

​

179,220

​

—

​

—

​

—

​

—

​

—

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(1)

February 2020 equity awards for Mr. Rickard and Dr. Shetzline were granted on the date specified in the preceding column and were subsequently ratified by the compensation and HR committee following the appointment of each individual as an executive officer of the company.

(2)

Consists of the target cash bonus payment for 2020 performance under our cash bonus program. As described in more detail elsewhere in this table relating to grants made priorproxy statement under the caption Cash Bonus, in 2020, Mr. Mallon had an individual bonus target of 75% of his base salary, Mr. McCourt had an individual bonus target of 60% of his base salary, Ms. Consylman and Mr. Rickard each had an individual bonus target of 50% of their respective base salaries, and Dr. Shetzline had an individual bonus target of 40% of his base salary. Seventy percent (70%) of bonuses awarded for performance in 2020 were tied solely to the dateachievement of our corporate goals for 2020, and 30% of bonuses awarded were tied to the achievement of corporate and individual performance goals. In determining Mr. Mallon's cash bonus for 2020, the board equated Mr. Mallon's individual performance with that of the Separation has not been adjustedcompany's performance. Actual bonus payments for 2020 performance are set forth in the impactSummary Compensation Table elsewhere in this proxy statement.

(3)

Awards listed in the "Estimated Future Payouts Under Equity Incentive Plan Awards" column represent threshold, target and maximum potential future payouts under the PSUs granted to each of the Separation. For information on the impact of the Separation on grants made priorour named executive officers in 2020. The PSUs are eligible to the date of the Separation, please refer to the footnotes that follow this table. For additional information on adjustments made to

vest based

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2020  Proxy Statement    5152    Ironwood

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outstanding equity awards in connection withon the Separation, please seeCompensation Discussion and Analysis—Equity Impactachievement of the Separation,certain performance goals over a two or three-year performance period, as described elsewhere in this proxy statement.statement under the caption 2020 Annual Equity Awards.

​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​
Name			Grant Date			Compensation and HR Committee Approval Date (if different than Grant Date)			Estimated Future Payouts Under Non- Equity Incentive Plan Awards(1) Target ($)			All Other Stock Awards: Number of Shares of Stock or Units (#)*			All Other Option Awards: Number of Securities Underlying Options (#)			Exercise or Base Price of Option Awards ($/Sh)			Grant Date Fair Value of Stock and Option Awards ($)(2)
​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​
Mark Mallon		​	1/9/2019	(3)	​	1/3/2019		​	—		​	93,036	(4)	​	—		​	—		​	1,146,204
​		​	1/9/2019	(3)	​	1/3/2019		​	—		​	—		​	171,526	(5)	​	12.32		​	999,516
​		​	4/1/2019	(6)	​	3/29/2019		​	—		​	206,873		​	—		​	—		​	2,546,607
​		​	4/1/2019	(6)	​	3/29/2019		​	—		​	—		​	423,049		​	14.02		​	2,804,815
​		​	—		​	—		​	562,500		​	—		​	—		​	—		​	—
Gina Consylman			1/29/2019			1/22/2019			—			72,500	(7)		—			—			935,250
			1/29/2019			1/22/2019			—			—			145,000	(8)		12.90			888,546
			12/16/2019	(9)		12/16/2019			—			41,150			—			—			532,481
			—			—			240,000			—			—			—			—
Halley E. Gilbert		​	1/29/2019		​	1/22/2019		​	—		​	72,500	(7)	​	—		​	—		​	935,250
​		​	1/29/2019		​	1/22/2019		​	—		​	—		​	145,000	(8)	​	12.90		​	888,546
​		​	12/16/2019	(9)	​	12/16/2019		​	—		​	41,150		​	—		​	—		​	532,481
​		​	—		​	—		​	240,000		​	—		​	—		​	—		​	—
Thomas A. McCourt			1/29/2019			1/22/2019			—			—			345,000	(10)		12.90			2,114,126
			5/1/2019	(11)		—			—			22,852			—			—			269,197
			5/1/2019	(11)		—			—			—			45,704			11.78			256,034
			12/16/2019	(9)		12/16/2019			—			115,220			—			—			1,490,947
			—			—			312,000			—			—			—			—
Peter M. Hecht, Ph.D		​	1/29/2019		​	1/22/2019		​	—		​	​		​	1,000,000	(12)	​	12.90		​	6,127,900
​		​	—		​	—		​	50,000		​	—		​	—		​	—		​	—
Mark G. Currie, Ph.D			1/29/2019			1/22/2019			—			—			600,000	(13)		12.90			3,676,740
			4/1/2019			—			—			2,995	(14)		—			—			41,990
			5/29/2019			—			—			22,706	(14)		—			—			244,317
			—			—			250,000			—			—			—			—
​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​

* Unless otherwise noted, all stock

(4)

Stock awards listed in the "All Other Stock Awards: Number of Shares of Stock or Units (#)" column are RSUs.

(1)  Consists of the target cash bonus payment for 2019 performance under our cash bonus program. As described in more detail elsewhere in this proxy statement under the captionCash Bonus, in 2019, Mr. Mallon had an individual bonus target of 75% of his base salary, 70% of which was tied solely to the achievement of our corporate goals for 2019 (which was not determined as of December 31, 2019) and 30% of which was tied to the achievement of corporate and individual performance goals (the range of which was not determined as of December 31, 2019). In determining Mr. Mallon's cash bonus for 2019, the compensation and HR committee equated Mr. Mallon's individual performance with that of the company overall. Mses. Consylman and Gilbert had an individual bonus target of 50% of their respective base salaries, 70% of which was tied solely to the achievement of our corporate goals for 2019 (which was not determined as of December 31, 2019) and 30% of which was tied to the achievement of corporate and individual performance goals (the range of which was not determined as of December 31, 2019). Mr. McCourt had an individual bonus target of 60% of his base salary (which percentage was increased from 50% in connection with his promotion to president in May 2019), 70% of which was tied solely to the achievement of our corporate goals for 2019 (which was not determined as of December 31, 2019) and 30% of which was tied to the achievement of corporate and individual performance goals (the range of which was not determined as of December 31, 2019). Actual bonus payments for 2019 performance are set forth in theSummary Compensation Table elsewhere in this proxy statement.

Dr. Hecht's bonus, with an individual bonus target of 50% of his base salary, was to be determined primarily based on the achievement of our corporate goals. Dr. Currie had an individual bonus target of 50% of his base salary, 70% of which was tied solely to the achievement of our corporate goals for 2019 (which was not determined as of December 31, 2019) and 30% of which was tied to the achievement of corporate and individual performance goals (the range of which was not determined as of December 31, 2019). Neither Dr. Hecht nor Dr. Currie received a bonus payment for 2019 performance because they transitioned to Cyclerion in connection with the Separation and, as a result, were not employed by Ironwood on the date in 2020 on which bonus payments for 2019 performance were made.

(2)  

(5)

Reflects the fair value of time-based RSU RSA and stock optionPSU awards on the date of grant calculated in accordance with ASC 718, excluding the effects of potential forfeitures.forfeitures, with the grant date fair value of PSUs determined based on the probable outcome of the performance conditions (target) associated with such awards on the grant date. For a discussion of the assumptions used in the valuation of the time-based RSU RSA and stock optionPSU awards granted to our named executive officers in 2019,2020, see footnote 1 to theSummary Compensation Table elsewhere in this proxy statement.

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52    Ironwood

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(3)  

(6)

Awarded to Mr. MallonDr. Shetzline in April 2020 as a recognition award in connection with his joining the company in January 2019.

(4)  Asdesignation as an executive officer of the date of the Separation, 93,036 RSUs were unvested. Unvested RSUs held as of the date of the Separation were converted into 104,536 unvested Ironwood RSUs.

(5)  As of the date of the Separation, no stock options were vested and 171,526 stock options were unvested. Unvested stock options held as of the date of the Separation were converted into 192,729 unvested Ironwood stock options with an exercise price of $10.97.

(6)  Awarded to Mr. Mallon in connection with his becoming chief executive officer in connection with the Separation in April 2019.

(7)  As of the date of the Separation, 72,500 RSUs were unvested. Unvested RSUs held as of the date of the Separation were converted into 81,462 unvested Ironwood RSUs.

(8)  As of the date of the Separation, 9,062 stock options were vested and 135,938 stock options were unvested. Vested stock options held as of the date of the Separation were converted into 9,062 vested Ironwood stock options with an exercise price of $11.49 and 906 vested Cyclerion stock options with an exercise price of $14.21. Unvested stock options held as of the date of the Separation were converted into 152,742 unvested Ironwood stock options with an exercise price of $11.49.

(9)  Awarded as a special RSU retention award in December 2019.

(10)  As of the date of the Separation, 21,562 stock options were vested and 323,438 stock options were unvested. Vested stock options held as of the date of the Separation were converted into 21,562 vested Ironwood stock options with an exercise price of $11.49 and 2,156 vested Cyclerion stock options with an exercise price of $14.21. Unvested stock options held as of the date of the Separation were converted into 363,420 unvested Ironwood stock options with an exercise price of $11.49.

(11)  Awarded to Mr. McCourt in connection with his promotion to president in April 2019.

(12)  As of the date of the Separation, 62,500 stock options were vested and 937,500 stock options were unvested. Vested stock options held as of the date of the Separation were converted into 62,500 vested Ironwood stock options with an exercise price of $11.49 and 6,250 vested Cyclerion stock options with an exercise price of $14.21. Unvested stock options held as of the date of the Separation were converted into 851,580 unvested Cyclerion stock options with an exercise price of $14.21.

(13)  As of the date of the Separation, 37,500 stock options were vested and 562,500 stock options were unvested. Vested stock options held as of the date of the Separation were converted into 37,500 Ironwood stock options with an exercise price of $11.49 and 3,750 Cyclerion stock options with an exercise price of $14.21. Unvested stock options held as of the date of the Separation were converted into 510,948 unvested Cyclerion stock options with an exercise price of $14.21.

(14)  Reflects RSAs received as compensation for service on our board of directors.

company.

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20202021  Proxy Statement    53

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Outstanding Equity Awards at Fiscal Year-End

As described elsewhere in thisour proxy statement underrelating to our 2020 annual meeting of stockholders, filed with the captionCompensation Discussion and Analysis—Equity Impact of the Separation,SEC on April 21, 2020, portions of certain Ironwood equity awards were converted into Cyclerion equity awards in connection with the Separation. The following tables set forth information regarding outstanding Ironwood and Cyclerion equity awards held by each of our named executive officers on December 31, 2019,2020, the last day of our last fiscal year. Information presented has been adjusted, as necessary, to reflect the impact of the Separation.

Ironwood Equity Awards at Fiscal Year-End

​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​
		Option Awards												Stock Awards
Name			Number of Securities Underlying Unexercised Options (#) Exercisable			Number of Securities Underlying Unexercised Options (#) Unexercisable			Option Exercise Price ($)			Option Expiration Date			Number of Shares of Units of Stock That Have Not Vested (#)(1)			Market Value of Shares or Units of Stock That Have Not Vested ($)(2)
​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​
Mark Mallon		​	—		​	192,729		​	10.97		​	1/9/2029	(3)	​	​		​	​
​		​	—		​	423,049		​	14.02		​	4/1/2029	(3)	​	​		​	​
​		​	—		​	—		​	​		​	​		​	311,409		​	4,144,854
Gina Consylman			43,563			—			13.78			7/1/2024	(3)
			8,500			—			13.91			3/16/2025	(4)
			5,077			—			10.20			9/16/2025	(4)
			29,993			702			9.12			3/1/2026	(4)
			8,161			8,075			13.60			1/2/2028	(4)
			29,986			35,113			12.95			2/21/2028	(4)
			36,216			125,588			11.49			1/29/2029	(4)
			—			—			—			—			174,014	(6)		2,316,126
Halley E. Gilbert		​	60,000		​	—		​	10.02		​	2/2/2020	(5)	​	​		​	​
​		​	60,000		​	—		​	9.89		​	2/1/2021	(5)	​	​		​	​
​		​	30,000		​	—		​	10.53		​	12/12/2021	(5)	​	​		​	​
​		​	45,000		​	—		​	13.11		​	2/1/2022	(5)	​	​		​	​
​		​	30,000		​	—		​	11.65		​	2/1/2023	(5)	​	​		​	​
​		​	25,000		​	—		​	10.25		​	12/2/2023	(5)	​	​		​	​
​		​	65,000		​	—		​	12.56		​	3/3/2024	(4)	​	​		​	​
​		​	57,500		​	—		​	13.91		​	3/16/2025	(4)	​	​		​	​
​		​	64,984		​	1,522		​	9.12		​	3/1/2026	(4)	​	​		​	​
​		​	59,982		​	24,344		​	14.93		​	2/27/2027	(4)	​	​		​	​
​		​	34,986		​	40,963		​	12.95		​	2/21/2028	(4)	​	​		​	​
​		​	36,216		​	125,588		​	11.49		​	1/29/2029	(4)	​	​		​	​
​		​	—		​	—		​	—		​	—		​	183,707	(7)	​	2,445,140
Thomas A. McCourt			20,000			—			10.02			2/2/2020	(5)
			99,988			—			9.89			2/1/2021	(5)
			95,971			—			13.11			2/1/2022	(5)
			110,962			—			11.65			2/1/2023	(5)
			80,504			—			12.56			3/3/2024	(4)
			97,500			—			13.91			3/16/2025	(4)
			174,959			4,097			9.12			3/1/2026	(4)
			118,089			47,929			14.93			2/27/2027	(4)
			65,595			76,809			12.95			2/21/2028	(4)
			86,170			298,812			11.49			1/29/2029	(4)
			6,665			39,039			11.78			5/1/2029	(4)
			—			—			—			—			171,252	(8)		2,279,364

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54    Ironwood

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		Option Awards															Stock Awards
Name			Number of Securities Underlying Unexercised Options (#) Exercisable			Number of Securities Underlying Unexercised Options (#) Unexercisable			Number of Securities Underlying Unexercised Unearned Options (#)			Option Exercise Price ($)			Option Expiration Date			Number of Shares or Units of Stock That Have Not Vested (#)			Market Value of Shares or Units of Stock That Have Not Vested ($)(1)			Equity Incentive Plan Awards: Number of Unearned Share, Units or Other Rights That Have Not Vested (#)			Equity Incentive Plan Awards: Market Value of Unearned Shares, Units or Other Rights That Have Not Vested ($)(1)
​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​
Mark Mallon		​	92,349		​	100,380		​	—		​	10.97		​	1/9/2029	(2)	​	—		​	—		​	—		​	—
​		​	202,711		​	200,338		​	—		​	14.02		​	4/1/2029	(2)	​	—		​	—		​	—		​	—
​		​	—		​	—		​	—		​	—		​	—		​	221,061	(8)	​	2,517,885		​	—		​	—
​		​	—		​	—		​	—		​	—		​	—		​	233,556	(9)	​	2,660,203		​	​		​	​
​		​	—		​	—		​	—		​	—		​	—		​	—		​	—		​	198,954	(10)	​	2,266,086
Gina Consylman			43,563			—			—			13.78			7/1/2024	(2)
			8,500			—			—			13.91			3/16/2025	(3)
			5,077			—			—			10.20			9/16/2025	(3)
			30,695			—			—			9.12			3/1/2026	(3)
			12,374			3,862			—			13.60			1/2/2028	(3)
			46,840			18,259			—			12.95			2/21/2028	(3)
			76,947			84,857			—			11.49			1/29/2029	(3)
			—			—			—			—			—			41,150	(7)		468,699			—			—
			—			—			—			—			—			68,327	(8)		778,245			—			—
			—			—			—			—			—			87,429	(9)		995,816			—			—
			—			—			—			—			—			—			—			61,494	(10)		700,417
Thomas McCourt		​	95,971		​	—		​	—		​	13.11		​	2/1/2022	(4)	​	​		​	​		​	​		​	​
​		​	110,962		​	—		​	—		​	11.65		​	2/1/2023	(4)	​	​		​	​		​	​		​	​
​		​	80,504		​	—		​	—		​	12.56		​	3/3/2024	(3)	​	​		​	​		​	​		​	​
​		​	97,500		​	—		​	—		​	13.91		​	3/16/2025	(3)	​	​		​	​		​	​		​	​
​		​	179,056		​	—		​	—		​	9.12		​	3/1/2026	(3)	​	​		​	​		​	​		​	​
​		​	162,331		​	3,687		​	—		​	14.93		​	2/27/2027	(3)	​	​		​	​		​	​		​	​
​		​	102,463		​	39,941		​	—		​	12.95		​	2/21/2028	(3)	​	​		​	​		​	​		​	​
​		​	183,082		​	201,900		​	—		​	11.49		​	1/29/2029	(3)	​	​		​	​		​	​		​	​
​		​	18,091		​	27,613		​	—		​	11.78		​	5/1/2029	(3)	​	​		​	​		​	​		​	​
​		​	—		​	—		​	—		​	—		​	—		​	115,220	(7)	​	1,312,356		​	—		​	—
​		​	—		​	—		​	—		​	—		​	—		​	100,482	(8)	​	1,144,490		​	—		​	—
​		​	—		​	—		​	—		​	—		​	—		​	36,800	(9)	​	419,152		​	—		​	—
​		​	—		​	—		​	—		​	—		​	—		​	—		​	—		​	90,435	(10)	​	1,030,055
Jason Rickard			18,041			—			—			11.65			2/1/2023	(3)
			7,754			—			—			11.76			6/10/2023	(3)
			10,309			—			—			9.66			12/16/2023	(3)
			40,834			—			—			12.02			11/3/2024	(3)
			—			—			11,236			13.11			2/1/2022	(5)
			2,000			—			—			13.11			2/1/2022	(6)
			15,550			—			—			13.91			3/16/2025	(3)
			6,046			—			—			9.79			9/1/2025	(3)
			17,956			—			—			9.12			3/1/2026	(3)
			39,535			43,598			—			11.49			1/29/2029	(3)
			5,426			8,285			—			11.78			5/1/2029	(3)
			—			—			—			—			—			41,153	(7)		468,733			—			—
			—			—			—			—			—			60,289	(8)		686,692			—			—
			—			—			—			—			—			60,616	(9)		690,416			—			—
			—			—			—			—			—			—			—			54,261	(10)		618,033
Michael Shetzline, M.D., Ph.D.		​	44,418		​	48,280		​	—		​	13.19		​	3/1/2029	(3)	​	​		​	​		​	​		​	​
​		​	—		​	—		​	—		​	—		​	—		​	43,869	(7)	​	499,668		​	—		​	—
​		​	—		​	—		​	—		​	—		​	—		​	48,875	(8)	​	556,686		​	—		​	—
​		​	—		​	—		​	—		​	—		​	—		​	11,586	(9)	​	131,965		​	—		​	—
​		​	—		​	—		​	—		​	—		​	—		​	—		​	—		​	43,989	(10)	​	501,035
​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

Option Awards

Stock Awards

Name

Number of Securities Underlying Unexercised Options (#) Exercisable

Number of Securities Underlying Unexercised Options (#) Unexercisable

Option Exercise Price ($)

Option Expiration Date

Number of Shares of Units of Stock That Have Not Vested (#)(1)

Market Value of Shares or Units of Stock That Have Not Vested ($)(2)

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

Peter M. Hecht, Ph.D.

​

125,000

​

—

​

10.02

​

2/2/2020

(5)

​

​

​

​

​

​

130,980

​

—

​

9.89

​

2/1/2021

(5)

​

​

​

​

​

​

292,467

​

—

​

13.11

​

2/1/2022

(5)

​

​

​

​

​

​

367,355

​

—

​

11.65

​

2/1/2023

(5)

​

​

​

​

​

​

318,229

​

—

​

12.56

​

3/3/2024

(4)

​

​

​

​

​

​

565,000

​

—

​

13.91

​

3/16/2025

(4)

​

​

​

​

​

​

723,125

​

—

​

9.12

​

3/1/2026

(4)

​

​

​

​

​

​

427,500

​

—

​

14.93

​

2/27/2027

(4)

​

​

​

​

​

​

181,250

​

—

​

12.95

​

2/21/2028

(4)

​

​

​

​

​

​

62,500

​

—

​

11.49

​

1/29/2029

(5)

​

​

​

​

​

​

—

​

—

​

—

​

—

​

—

​

—

Mark G. Currie, Ph.D.

8,888

—

10.02

2/2/2020

(5)

101,971

—

13.11

2/1/2022

(5)

190,383

—

11.65

2/1/2023

(5)

83,229

—

12.56

3/3/2024

(4)

131,250

—

13.91

3/16/2025

(4)

25,000

—

13.91

3/16/2025

(9)

107,707

—

9.12

3/1/2026

(4)

140,625

—

14.93

2/27/2027

(4)

67,187

—

12.95

2/21/2028

(4)

37,500

—

11.49

1/29/2029

(4)

—

—

—

—

22,706

(10)

302,217

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

​

(1)  Unless otherwise indicated, awards in this column reflect RSUs that vest over four years as to 25% of the award on each approximate anniversary of the grant thereof.

(2)  

Market value is calculated by multiplying the number of RSUs or RSAs that have not vested byreflects the closing price of our Class A common stock on the Nasdaq Global Select Market on December 31, 2019,2020, the last day of our fiscal year, which was $13.31.$11.39.

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54    Ironwood

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(3)  

Table of Contents

​

​

(2)

The options vest as to 25% of the shares on the first anniversary of the vesting commencement date and 1/48th of the shares each month thereafter for the next 36 months, generally subject to the executive's continued employment with the company on the applicable vesting date.

(4)  

(3)

The options vest as to 1/48th of the shares on each monthly anniversary of the vesting commencement date, generally subject to the executive's continued employment with the company on the applicable vesting date, until fully vested.

(5)  date.

(4)

The options vestvested as to 1.25% on each monthly anniversary of the vesting commencement date for the first 36 months, and as to 4.5833% of the award on each monthly anniversary thereafter, until fully vested, generally subject to the executive's continued employment with the company on the applicable vesting date.

(5)

The option vests upon global pharmaceutical product net sales (including partnered or licensed product revenue) exceeding $1 billion, generally subject to the executive's continued employment with the company on the applicable vesting date.

(6)  Includes 41,150 RSUs held

This option vested upon the acceptance by Ms. Consylman, whichthe U.S. FDA of an NDA for DUZALLO® (lesinurad).

(7)

RSUs vest in full on November 18, 2021, generally subject to continued employment with the company.

(8)

RSUs vest over three years as to 33.3% of the award on each approximate anniversary of the grant thereof, generally subject to continued employment with the company on the applicable vesting date.

(7)  Includes 41,150

(9)

RSUs that were awardedvest over four years as to Ms. Gilbert, which were to vest in full25% of the award on November 18, 2021, but were terminated in their entirety in connection with Ms. Gilbert's resignation fromeach approximate anniversary of the company effective February 2020.

(8)  Includes 115,220 RSUs held by Mr. McCourt, which vest in full on November 18, 2021,grant thereof, generally subject to continued employment with the company on the applicable vesting date.

(9)

(10)

PSUs vest over a two- to three-year period based on the achievement of the performance metrics discussed elsewhere in this proxy statement under the caption 2020 Annual Equity Awards. The option vested asnumber of shares reported in this column assumes target performance for NDA Acceptance PSUs and the 2020 rTSR PSUs and maximum performance for the Adjusted EBITDA PSUs, in each case in accordance with SEC requirements. Actual payouts for the PSUs could range from 0% to 25,000 shares upon200% of the first-dosingtarget number of PSUs subject to an award based on actual performance results. PSUs also have a service-based vesting condition that generally will be satisfied by continued employment with the company through the last day of the applicable performance period. For a discussion of the treatment of PSUs following certain terminations of employment and/or a change of control of Ironwood, please see Named Executive Officer Severance Arrangements and Benefits in the first clinical studyEvent of the next phase following achievementa Change of proofControl elsewhere in this proxy statement.

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2021  Proxy Statement    55

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Table of concept for the first internally derived or externally accessed product (other than linaclotide) qualified by our compensation and HR committee as targeting a new indication, category or market.Contents

(10)  The RSAs vest as to 100% of the shares on the date immediately preceding the 2020 annual meeting of stockholders, subject to continued service as a director on the vesting date.

​

​

Cyclerion Equity Awards at Fiscal Year-End

The Cyclerion equity awards reflected in the following table were granted to Ms. Consylman and Messrs. McCourt and Rickard in connection with the Separation. Each Ironwood equity award that was converted into a Cyclerion equity award is subject to substantially the same terms and vesting conditions as were applicable to the Ironwood equity awards prior to the distribution. The following table doesNeither Mr. Mallon nor Dr. Shetzline hold any Cyclerion equity awards.

​	​	​	​	​	​	​	​	​	​	​
Name		Number of Securities Underlying Unexercised Options (#) Exercisable			Option Exercise Price ($)			Option Expiration Date
​	​	​	​	​	​	​	​	​	​	​
Gina Consylman		​	1,117		​	17.05		​	7/1/2024
​		​	850		​	17.20		​	3/16/2025
​		​	437		​	12.61		​	9/16/2025
​		​	2,437		​	11.28		​	3/1/2026
​		​	500		​	16.82		​	1/2/2028
​		​	1,875		​	16.02		​	2/21/2028
​		​	906		​	14.21		​	1/29/2029
Thomas McCourt			5,464			12.24			2/1/2021
			8,713			16.21			2/1/2022
			10,221			14.40			2/1/2023
			7,591			15.54			3/3/2024
			9,750			17.20			3/16/2025
			14,218			11.28			3/1/2026
			8,859			18.47			2/27/2027
			4,101			16.02			2/21/2028
			2,156			14.21			1/29/2029
Jason Rickard		​	200		​	16.21		​	2/1/2022
​		​	857		​	14.40		​	2/1/2023
​		​	543		​	14.55		​	6/10/2023
​		​	750		​	11.95		​	12/16/2023
​		​	3,324		​	14.87		​	11/3/2024
​		​	1,555		​	17.20		​	3/16/2025
​		​	562		​	12.11		​	9/1/2025
​		​	1,425		​	11.28		​	9/1/2026
​		​	465		​	14.21		​	1/29/2029
​	​	​	​	​	​	​	​	​	​	​

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2020  Proxy Statement    5556    Ironwood

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Table of Contents

​

​

not include any Cyclerion equity awards that may have been granted by Cyclerion to Drs. Hecht and Currie following the Separation.

​	​	​	​	​	​	​	​	​	​	​	​	​	​
Name			Number of Securities Underlying Unexercised Options (#) Exercisable			Number of Securities Underlying Unexercised Options (#) Unexercisable			Option Exercise Price ($)			Option Expiration Date
​	​	​	​	​	​	​	​	​	​	​	​	​	​
Mark Mallon		​	—		​	—		​	—		​	—
Gina Consylman			1,117			—			17.05			7/1/2024
			850			—			17.20			3/16/2025
			437			—			12.61			9/16/2025
			2,437			—			11.28			3/1/2026
			500			—			16.82			1/2/2028
			1,875			—			16.02			2/21/2028
			906			—			14.21			1/29/2029
Halley E. Gilbert		​	5,999		​	—		​	12.39		​	2/2/2020
​		​	6,000		​	—		​	12.24		​	2/1/2021
​		​	2,999		​	—		​	13.03		​	12/12/2021
​		​	4,499		​	—		​	16.21		​	2/1/2022
​		​	2,999		​	—		​	14.40		​	2/1/2023
​		​	2,499		​	—		​	12.68		​	12/2/2023
​		​	6,499		​	—		​	15.54		​	3/3/2024
​		​	5,750		​	—		​	17.20		​	3/16/2025
​		​	5,281		​	—		​	11.28		​	3/1/2026
​		​	4,500		​	—		​	18.47		​	2/27/2027
​		​	2,187		​	—		​	16.02		​	2/21/2028
​		​	906		​	—		​	14.21		​	1/29/2029
Thomas A. McCourt			1,999			—			12.39			2/2/2020
			5,464			—			12.24			2/1/2021
			8,713			—			16.21			2/1/2022
			10,221			—			14.40			2/1/2023
			7,591			—			15.54			3/3/2024
			9,750			—			17.20			3/16/2025
			14,218			—			11.28			3/1/2026
			8,859			—			18.47			2/27/2027
			4,101			—			16.02			2/21/2028
			2,156			—			14.21			1/29/2029
Peter M. Hecht, Ph.D.		​	12,499		​	—		​	12.39		​	2/2/2020
​		​	53,083		​	—		​	12.24		​	2/1/2021
​		​	36,088		​	—		​	16.21		​	2/1/2022
​		​	43,679		​	—		​	14.40		​	2/1/2023
​		​	37,972		​	—		​	15.54		​	3/3/2024
​		​	56,500		​	—		​	17.20		​	3/16/2025
​		​	207,051		​	16,842		​	11.28		​	3/1/2026
​		​	157,809		​	186,968		​	18.47		​	2/27/2027
​		​	105,933		​	274,397		​	16.02		​	2/21/2028
​		​	157,642		​	700,188		​	14.21		​	1/29/2029
Mark G. Currie, Ph.D.			888			—			12.39			2/2/2020
			37,279			—			12.24			2/1/2021
			17,490			—			16.21			2/1/2022
			27,772			—			14.40			2/1/2023
			9,930			—			15.54			3/3/2024
			15,625			22,708			17.20			3/16/2025
			46,347			4,447			11.28			3/1/2026
			51,910			61,503			18.47			2/27/2027
			39,268			101,716			16.02			2/21/2028
			94,588			420,110			14.21			1/29/2029
​	​	​	​	​	​	​	​	​	​	​	​	​	​

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56    Ironwood

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Table of Contents

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Option Exercises and Stock Vested Table

The following table sets forth certain information regarding the exercise of options to purchase our Class A common stock and the vesting of RSUs and RSAs that were held by our named executive officers during the year ended December 31, 2019.2020.

​	​	​	​	​	​	​	​		​	​	​	​	​	​	​	​	​	​	​	​		​	​	​	​	​
			Option Awards						Stock Awards						Option Awards						Stock Awards
​		​	​	​	​	​	​	​	​	​	​	​	​
Name			Number of Shares Acquired on Exercise (#)			Value Realized on Exercise ($)(1)			Number of Shares Acquired on Vesting (#)			Value Realized on Vesting ($)(2)				Number of Shares Acquired on Exercise (#)			Value Realized on Exercise ($)(1)			Number of Shares Acquired on Vesting (#)			Value Realized on Vesting ($)(2)
​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​	​
Mark Mallon		​	—		​	—		​	—		​	—			​	—		​	—		​	77,853		​	839,334
Gina Consylman			—			—			38,116			482,063				—			—			45,435			535,562
Halley E. Gilbert		​	40,449	(3)	​	274,365		​	47,545		​	642,588
Thomas A. McCourt			220,000	(4)		959,452			29,577			380,076
Peter M. Hecht, Ph.D.		​	130,000	(5)	​	958,114		​	—		​	—
Mark G. Currie, Ph.D.			—			—			21,946	(6)		266,820	(7)
Thomas McCourt															​	119,988	(3)	$	284,331		​	19,232		​	220,407
Jason Rickard																—			—			31,074			363,220
Michael Shetzline, M.D., Ph.D.															​	—		​	—		​	3,863		​	46,395
​	​	​	​	​	​	​	​		​	​	​	​	​	​	​	​	​	​	​	​		​	​	​	​	​

(1)

Computed by determining the difference between the market price of our Class A common stock uponon the date of exercise and the exercise price of the exercised stock option, in each case on the date of exercise, multiplied by the number of shares acquired upon exercise of the option.

(2)

Computed by multiplying the number of shares of Class A common stock underlying the vested RSUs or RSAs by the market price of our Class A common stock on the vesting date.

(3)

Includes 20,44999,988 shares of our Class A common stock that Ms. GilbertMr. McCourt acquired through an option exercise as such stock options were expiring, of which 81,089 shares were surrendered to the company in a net share settlement and then held,18,899 shares were retained by Mr. McCourt, thereby increasing herhis ownership of our Class A common stock by such amount. Also includes 20,000 shares of our Class A common stock that Ms. Gilbert acquired through option exercises as such stock options were expiring, and then sold on the open market.

(4)  Represents 220,000 shares of our Class A common stock that Mr. McCourt acquired through option exercises as such stock options were expiring, and then sold on the open market.

(5)  Includes 20,449 shares of Class A common stock that Dr. Hecht acquired through an option exercise, as such stock options were expiring, and then held, thereby increasing his ownership of our Class A common stock by such amount. Also includes 109,551 shares of our Class A common stock that Dr. Hecht acquired through option exercises as such stock options were expiring, and then sold on the open market to satisfy tax withholding obligations.

(6)  Includes (a) 18,951 shares of Class A common stock that Dr. Currie acquired through the vesting of RSUs granted in connection with Dr. Currie's employment with the company and (b) 2,995 shares of our Class A common stock that Dr. Currie acquired through the vesting of RSAs granted in April 2019 in connection with his joining our board of directors.

(7)  Includes (a) $224,830 attributable to the vesting of RSUs, which were granted in connection with Dr. Currie's employment with the company, and (b) $41,990 attributable to the vesting of RSAs, which were granted in connection with Dr. Currie's joining our board of directors in April 2019.

Named Executive Officer Severance Arrangements and Benefits in the Event of a Change of Control

We have entered into severance arrangements with each of our named executive officers. Under the severance arrangements, our named executive officers are eligible to receive certain payments and benefits in the event of an involuntary termination without "cause" or a "constructive termination." Each of our executives is also are eligible to receive enhanced payments and benefits in the event of a change of control plus an actual or constructive involuntary termination of employment ("(such double trigger"trigger event, a "change of control termination"). For additional information, please see the definition of "change of control termination," below. UnlessThe following descriptions reflect the context suggested otherwise, "named executive officers" as used in this section referspayments and benefits that would have been payable to each of our named executive officers who remained atas of December 31, 2020 under their respective severance arrangements.

The benefits for our named executive officers described elsewhere in this proxy statement under the company followingcaptions Severance Benefits not in Connection with a Change of Control and Change of Control Severance Benefits are only payable if the Separation.named executive officer complies with all of Ironwood's rules and policies, executes a separation agreement that includes a release of claims and complies with any post employment non-disclosure, non-competition and non-solicitation obligations. The executive severance agreements further provide that in connection with the sale of all or substantially all of the assets of Ironwood, Ironwood would cause the acquirer of such assets to assume the executives' severance arrangements.

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Severance Benefits not in Connection with a Change of Control

In the event of a termination without cause or a constructive termination not qualifying as a change of control termination, each of our named executive officers would be entitled to receive (i) a lump-sum payment equal to 12 months of his or her base salary for the year of termination, plus an amount equal to a maximum of six months of his or her base salary for anythe period beginning as of the first anniversary of his or her termination date, provided he or she has not secured new, reasonably similar full-time employment (for Mr. Mallon,our former chief executive officer, a lump-sum payment equal to 18 months of his base salary for the year of termination); (ii) a lump-sum payment equal to his or her target cash bonus for the year of termination, pro-rated based on the percentage of the year worked prior to the triggering event; (iii) a lump-sum payment equal to his or her actual bonus for the prior year if not yet paid as of the termination date; (iv) a lump-sum payment equal to his or her full target cash bonus for the year of termination (for Mr. Mallon,our former chief executive officer, multiplied by 1.5); (v) 12 months of subsidized COBRA benefits, plus up to an additional six months of subsidized COBRA benefits for anythe period beginning as of the first anniversary of his or her termination date, provided he or she has not been eligible to participate in the group medical plan of another employer (for Mr. Mallon,our former chief executive officer, 18 months of subsidized COBRA benefits); and (vi) outplacement assistance benefits. The non-equity based severance benefits described in items (i) through (vi) of this paragraph, collectively, are referred to as the "Non-Equity"Non Equity Severance Benefits."

In addition, each executive severance agreement provides that any outstanding equity awards subject solely to time-based vesting would vest as to (1) the portion of the equity award that would have vested if the named executive officer had remained employed for 18 months (for Mr. Mallon,our former chief executive officer, 24 months) following the termination date and (2) an additional portion of the equity award that would have vested on the next regular vesting date after such 18-month period (for Mr. Mallon,our former chief executive officer, such 24-month24 month period) as if the equity award vested on a daily basis from the last regular award vesting date occurring prior to the end of the 18-month18 month period (for Mr. Mallon,our former chief executive officer, the 24-month24 month period) through such next regular vesting date. Any equity awards that do not vest pursuant to the preceding sentence would remain outstanding and eligible to vest upon the occurrence of a change of control termination (as defined below) in the time periods described below for such a termination (for Ms. Gilbert, such shares that otherwise would be cancelled shall remain outstanding for 24 months and vest if, within that time period, the company enters into a definitive agreement that, if consummated, would result in a change of control).termination. Further, the exercisability of any outstanding vested stock options held by the named executive officer as of the termination date (including, other than for Ms. Gilbert,our former chief executive officer and Dr. Shetzline, any vested options to purchase Cyclerion common stock that were granted in connection with the Separation in substitution for or replacement of vested options to purchase Ironwood Class A common stock) would be extended through the earlier of 24 months (for Mr. Mallon,our former chief executive officer, 36 months) following the termination date (or, in the event that Ironwood publicly announced it was conducting negotiations leading to a change of control or entered into a definitive agreement that would have resulted in a change of control during such 24-month24 month period (for Mr. Mallon,our former chief executive officer, such 36-month36 month period), the later of (A) the expiration of the 24-month24 month period (for Mr. Mallon,our former chief executive officer, the 36-month36 month period) or (B) the first to occur of the date that is three months following the change of control and 30 days following the date on which Ironwood announced that such definitive agreement had been terminated or that Ironwood's efforts to consummate the change of control contemplated by the previously-announcedpreviously announced negotiations or by a previously executed definitive agreement had been abandoned) or the stock option's final expiration date. The equity-based severance benefits described in this paragraph are referred to as the "Equity Severance Benefits."

Moreover, with respect to PSUs, in the event of the named executive officer's involuntary termination without cause or constructive termination (collectively, a "qualifying termination"), the awards, to the extent then outstanding, will not terminate upon such termination of employment and instead will remain eligible to vest based on the attainment of the applicable performance goals. Specifically, the NDA Acceptance PSUs will generally remain outstanding and eligible to vest based upon the achievement of an NDA performance goal until

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the earlier of (A) the end of the performance period or (B) the twelve (12)-month period following the date of the qualifying termination. The Adjusted EBITDA PSUs and the 2020 rTSR PSUs will generally remain outstanding and eligible to vest based upon the achievement of the cumulative adjusted organic EBITDA and rTSR performance goals, respectively, until the end of the applicable performance period, with the number of PSUs actually delivered subject to proration based on the number of days the named executive officer remained employed during the applicable performance period.

Change of Control Severance Benefits

In the event of a change of control termination, each of our named executive officers would be entitled to receive the following benefits under his or her executive severance agreement: (1) a lump-sum payment in an amount equal to 18 months (for Mr. Mallon,our chief executive officer, 24 months) of his or her base salary as of the time of termination; (2) a lump-sum payment of his or her target cash bonus for the year of termination, pro-rated based on the percentage of the year worked prior to the triggering event; (3) a lump-sum payment equal to his or her actual bonus for the prior year if not yet paid as of the termination date; (4) a lump-sum payment equal to his or her full target cash bonus for the year of termination,

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multiplied by 1.5 (for Mr. Mallon,our former chief executive officer, multiplied by 2.0); (5) 18 months (for Mr. Mallon,our former chief executive officer, 24 months) of subsidized COBRA benefits; and (6) outplacement assistance benefits.

In addition, in the event of a change of control termination, each executive severance agreement provides for acceleration of all outstanding equity awards subject solely to time-based vesting as of the later of (1) the termination date or (2) the change of control. Further, the exercisability of any outstanding vested stock options held by the named executive officer as of the termination date (including, other than for our former chief executive officer and Dr. Shetzline, any vested options to purchase Cyclerion common stock granted in connection with the Separation in substitution for or replacement of vested options to purchase Ironwood Class A common stock) would be extended through the earlier of 24 months (for Mr. Mallon,our former chief executive officer, 36 months) following the termination date (or, if later the date that was three months following the change of control) or the stock option's final expiration date.

Under each executive severance agreement, a "change of control termination" consists of an involuntary termination without "cause" or a "constructive termination" (each as defined in the agreement), in either event during the period commencing six months prior to the earlier of (1) the date that Ironwood first publicly announces it is conducting negotiations leading to a change of control, or (2) the date that Ironwood enters into a definitive agreement that would result in a change of control, and ending on the earlier of (A) the date on which Ironwood announces that the definitive agreement has been terminated or the negotiations have been abandoned or (B) the date that is 24 months after the change of control. Under each executive severance agreement, a change of control occurs when: (I) any person becomes, pursuant to a transaction or a series of transactions not approved by the Ironwood board of directors, the beneficial owner, directly or indirectly, of Ironwood securities representing more than 50% of the total voting power; (II) a merger or consolidation of Ironwood occurs, whether or not approved by the Ironwood board of directors, which results in the holders of Ironwood's voting securities holding less than 50% of the combined voting power of the surviving entity immediately after such merger or consolidation; (III) the sale or disposition of more than two-thirds of the assets of Ironwood; or (IV) the date a majority of members of the Ironwood board of directors is replaced during any 12-month period by directors whose appointment or election was not endorsed by a majority of members of the Ironwood board of directors before the date of the appointment or election.

Treatment of PSUs in the Event of a Change of Control

In the event of a change of control of Ironwood, the performance- and service-based vesting conditions applicable to the PSUs, to the extent then outstanding, will generally be treated as follows: the NDA Acceptance

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PSUs and Adjusted EBITDA PSUs will become earned at target (and subject to vesting as described below) as of immediately prior to the change of control, provided that if the NDA Acceptance PSUs had already been earned at target as of the change of control, no additional portion of such NDA Acceptance PSUs will become earned as a result of the change of control. The benefits2020 rTSR PSUs will become earned at target (and subject to vesting as described below) as of immediately prior to the change of control, provided that if the resulting rTSR percentile rank, determined after accounting for the stock price performance of Ironwood stock in connection with the change of control, would result in the 2020 rTSR PSUs being earned above target, the 2020 rTSR PSUs will be deemed to be earned (and subject to vesting as described below) at such higher level in accordance with the terms of the award.

Any PSUs that become earned in connection with a change of control as described above for ourshall vest in equal installments on a quarterly basis over the remaining portion of the applicable performance period, generally subject to a named executive officers are only payable ifofficer's continued employment on each such vesting date. In the event of the occurrence of a qualifying termination in connection with or during the 24-month period immediately following the change of control and prior to the completion of the performance period, any earned but unvested PSUs held by the named executive officer complies with all of Ironwood's rules and policies, executes a separation agreement that includes a release of claims and complies with his or her post-employment non-disclosure, non-competition and non-solicitation obligations. The executive severance agreements further provide thatwill immediately vest in full in connection with such qualifying termination. If a named executive officer underwent a qualifying termination prior to a change of control, any outstanding PSUs held by the sale of all or substantially allnamed executive officer as of the assetstime of Ironwood, Ironwoodthe change of control would causebecome earned as described in the acquirerpreceding paragraph but, in the case of such assetsthe Adjusted EBITDA PSUs and the 2020 rTSR PSUs, remain subject to assumeproration based on the arrangements.number of days the named executive officer remained employed during the applicable performance period.

Treatment of Equity in the Event of Death or Permanent Disability

For all employees, including our named executive officers, outstanding stock option and RSU awards subject solely to time-based vesting accelerate in full in the event of the death of the award holder. This term applies to all outstanding time-based stock option and RSU awards made under our equity incentive plans, including the 2019 Plan. Our current form of stock option and RSU agreements for awards issued under our 2019 Plan include similar provision for the acceleration of unvested time-based awards upon the death of an award holder, including our named executive officers. In addition, the post-termination exercise window of all vested stock options held by a participant that were granted under our Amended and Restated 2005 Stock2010 Employee, Director and Consultant Equity Incentive Plan, 2010 Plan and 2019 Plan is extended to one year (or the stock option's final expiration date, if earlier) following the participant's termination of employment by reason of his or her death.

With respect to PSUs, in the event of a termination of the named executive officer's employment as a result of his or her death or permanent disability, the awards, to the extent then outstanding, will not terminate and will remain eligible to vest based on the attainment of the applicable performance goals. Specifically, the NDA Acceptance PSUs will generally remain outstanding and eligible to vest based upon the achievement of the NDA acceptance performance goal until the earlier of (A) the end of the performance period or (B) the twelve (12)-month period following the death or permanent disability. The Adjusted EBITDA PSUs and 2020 rTSR PSUs will generally remain outstanding and eligible to vest based upon the achievement of applicable performance goals until the end of the applicable performance period, with the number of PSUs actually delivered subject to proration based on the number of days the named executive officer remained employed during the applicable performance period.

Separation AgreementEmployee Proprietary Information, Intellectual Property and Non-competition Agreements

In connection with her resignation in February 2020, Ms. GilbertThe employee proprietary information, intellectual property and non-competition agreement that the company entered into a separation agreement with our former chief executive officer provides that, in the event the company which agreement generally serveddetermined to implementenforce the terms of Ms. Gilbert's existing severance agreement.

The separation agreement, whichnon-competition restriction included therein and a general release of claims, providedcourt determined that in exchange for Ms. Gilbert's signing and not revoking the separation agreement within the period set forth therein, the company would providesuch provision was

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Ms. Gilbert with the Non-Equity Severance Benefits and the Equity Severance Benefits, in each case as defined above, with the lump-sum payment described in item (i) above equal to Ms. Gilbert's annual base salaryunenforceable for lack of $480,000 (plus up to six months of salary continuation as described above), and the lump-sum payments described in items (ii)-(iv) above equal to the sum of the following: (A) $340,080 (representing Ms. Gilbert's annual bonus for 2019 determined based on actual performance); (B) $38,111 (representing Ms. Gilbert's pro-rated amount of annual target bonus for 2020); and (C) $240,000 (representing Ms. Gilbert's annual target bonus for 2020). The estimated aggregate cost associated with providing Ms. Gilbert with outplacement assistance benefits and 12 months of contributions towards the cost of COBRA coverage is $60,000 and approximately $24,000, respectively. With respect to the Equity Severance Benefits provided to Ms. Gilbert, the number of unvested Ironwood equity awards that were accelerated as described above were 115,571 stock options and 56,736 RSUs and the number of unvested equity awards that were not subject to the accelerated vesting described above but that will remain outstanding (but will not continue to vest) and will vest immediately if, within the 24-month period following the separation date, the company enters into a definitive agreement that would result in a change of control were 61,513 stock options and 35,258 RSUs. In addition, under her separation agreement,consideration, the company will not seek reimbursement from Ms. Gilbertprovide for the valuepayment of certain conference attendance registration fees followingat least 50% of the separation date,former chief executive officer's highest annualized base salary in the total valuelast two years prior to the last day of which is not expected to exceed $2,500.

By executingour chief executive officer's employment for the separation agreement, Ms. Gilbert acknowledged and reaffirmed her obligations under herlength of the non-competition period as additional consideration for such non-competition provisions. In addition, the employee proprietary information, intellectual property and inventions and noncompetition agreement, including her agreement to (1) protect the company's confidential information, as well as confidential information acquired during employment of any third parties, for the term of her employment and perpetually thereafter; (2) assign tonon-competition agreements that the company all right, titleentered into with Mr. McCourt and interest in and to any inventions made during the course of employment; and (3) during the term of employment andDr. Shetzline provide for an extended exercisability period for vested, unexercised nonqualified stock options for one year thereafter, refrain from (A) engagingthe last date of employment in any business activity which is in competition with Ironwood's business, (B) soliciting or doing business with any customer or potential customer ofthe event that the company and (C) employing or permitting any future employer or organization under her controldetermines to employ any person who at any time during her employment was an agent, representative or consultantenforce the non-competition restriction included in such agreement.

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Potential Payments Upon Termination or Change of Control

Except as described in this proxy statement, there are currently no other agreements or arrangements pursuant to which our named executive officers would receive severance or other benefits in the event of a separation fromtermination of employment or change of control of Ironwood. The following table presents our estimate of the amount of severance and other benefits to which our named executive officers would be entitled if a terminationtriggering event described below occurred on December 31, 2019 under the circumstances set forth in the column headings.2020. The closing price of our Class A common stock as listed on the Nasdaq Global Select Market on December 31, 20192020 was $11.39 per share. As described above, Mr. Mallon terminated employment on March 12, 2021 and, in connection with such termination, did not receive any severance benefits from the company.

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					Involuntary Termination without Cause or a Constructive Termination (1)			Qualifying Termination In Connection with or Following a Change of Control			Death(2)
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Mark Mallon		Cash Severance		$	1,158,750		$	1,545,000		​	—
​		Non-Equity Incentive Plan Compensation		$	1,448,438		$	1,738,125		​	—
​		Equity Acceleration(4)		​	​		​	​		​	​
​		Options		$	41,942		$	42,160		$	42,160
​		RSUs		$	4,786,089		$	5,178,088		$	5,178,088
​		PSUs		​	—		$	2,517,885		​	—
​		Other Benefits(5)		$	99,139		$	112,185		​	​
​		Total		$	7,534,358		$	11,133,442		$	5,220,247
Gina Consylman		Cash Severance(3)		$	741,600		$	741,600			—
		Non-Equity Incentive Plan Compensation		$	494,400		$	618,000			—
		Equity Acceleration(4)
		Options			—			—			—
		RSUs		$	1,921,482		$	2,242,759		$	2,242,759
		PSUs			—		$	778,245			—
		Other Benefits(5)		$	99,139		$	99,139
		Total		$	3,256,621		$	4,479,743		$	2,242,759
Thomas McCourt		Cash Severance(3)		$	834,600		$	834,600		​	—
​		Non-Equity Incentive Plan Compensation		$	667,680		$	834,600		​	—
​		Equity Acceleration(4)		​	​		​	​		​	​
​		Options		​	—		​	—		​	—
​		RSUs		$	2,568,992		$	2,875,998		$	2,875,998
​		PSUs		​	—		$	1,144,490		​	—
​		Other Benefits(5)		$	74,144		$	74,144		​	—
​		Total		$	4,145,416		$	5,763,832		$	2,875,998
Jason Rickard		Cash Severance(3)		$	685,125		$	685,125			—
		Non-Equity Incentive Plan Compensation		$	456,750		$	570,938			—
		Equity Acceleration(4)
		Options			—			—			—
		RSUs		$	1,598,040		$	1,845,841		$	1,845,841
		PSUs			—		$	686,692			—
		Other Benefits(5)		$	57,094		$	57,094			—
		Total		$	2,797,009		$	3,845,689		$	1,845,841
Michael Shetzline, M.D., Ph.D.		Cash Severance(3)		$	672,075		$	672,075		​	—
​		Non-Equity Incentive Plan Compensation		$	358,440		$	448,050		​	—
​		Equity Acceleration(4)		​	​		​	​		​	​
​		Options		​	—		​	—		​	—
​		RSUs		$	1,020,066		$	1,188,319		$	1,118,319
​		PSUs		​	—		$	556,686		​	—
​		Other Benefits(5)		$	53,766		$	53,766		​	—
​		Total		$	2,104,347		$	2,918,896		$	1,188,319
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$13.31 per share. Drs. Hecht and Currie are not included in the table below because they transitioned to Cyclerion in April 2019 in connection with the Separation.

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					Involuntary Termination without Cause or a Constructive Termination(1)			Termination Following a Change of Control			Death(2)
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Mark Mallon		Cash Severance		$	1,125,000		$	1,500,000		​	​
​		Non-Equity Incentive Plan Compensation		$	1,406,250		$	1,687,500		​	​
​		Equity Acceleration(4)		​	​		​	​		​	​
​		Options		$	328,843		$	450,986		$	450,986
​		RSUs		$	2,417,828		$	4,144,854		$	4,144,854
​		Other Benefits(5)		$	96,234		$	96,234		​	​
​		Total		$	5,374,155		$	7,879,574		$	4,595,840
Gina Consylman		Cash Severance(3)		$	720,000		$	720,000
		Non-Equity Incentive Plan Compensation		$	480,000		$	600,000
		Equity Acceleration(4)
		Options		$	123,239		$	163,337		$	163,337
		RSUs		$	1,673,826		$	1,789,583		$	1,789,583
		Other Benefits(5)		$	96,234		$	96,234
		Total		$	3,093,299		$	3,369,154		$	1,952,920
Halley E. Gilbert*		Cash Severance(3)		$	720,000		$	720,000		​	​
​		Non-Equity Incentive Plan Compensation		$	480,000		$	600,000		​	​
​		Equity Acceleration(4)		​	​		​	​		​	​
​		Options		$	128,191		$	168,795		$	168,795
​		RSUs		$	1,801,069		$	1,906,138		$	1,906,138
​		Other Benefits(5)		$	96,234		$	96,234		​	​
​		Total		$	3,225,494		$	3,491,167		$	2,074,933
Thomas A. McCourt		Cash Severance(3)		$	780,000		$	780,000
		Non-Equity Incentive Plan Compensation		$	624,000		$	780,000
		Equity Acceleration(4)
		Options		$	327,868		$	431,435		$	431,435
		RSUs		$	1,831,536		$	2,098,122		$	2,098,122
		Other Benefits(5)		$	73,171		$	73,171
		Total		$	3,636,575		$	4,162,728		$	2,529,557
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* Ms. Gilbert resigned from the company effective February 28, 2020. Information on separation payments and benefits provided to Ms. Gilbert in connection with her resignation is available elsewhere in this proxy statement under the captionNamed Executive Officer Severance Arrangements—Separation Agreement.

(1)

Represents amounts payable under the terms of the named executive officer severance arrangements. Non-equity incentive plan compensation payment amount assumes no bonus amounts for 20192020 have been paid to the executive as of December 31, 2019,2020, and that all 20182019 bonus amounts have been paid as of such date, in each case, as would be consistent with Ironwood's historical practice.

(2)

With respect to options, reflects the in-the-money value of the unvested portion of such named executive officer's options that have vesting provisions based solely on time, and not performance milestones, and that would be fully accelerated, in each case, in accordance with the terms of the award agreements issued under our equity incentive plans.plans in connection with his or her death. The value is calculated by multiplying the amount (if any) by which $13.31,$11.39, the closing price of our Class A common stock on the Nasdaq Global Select Market on December 31, 2019,2020, exceeds the exercise price of the option by the number of shares subject to the accelerated portion of the option.

With respect to RSUs, the value is calculated by multiplying the number of unvested RSUs with vesting provisions based solely on time that would be fully accelerated (if any) in connection with the named executive officer's death by $13.31,$11.39, the closing price of our Class A common stock on the Nasdaq Global Select Market on December 31, 2019,2020, in accordance with the terms of the award agreements issued under our equity incentive plans.

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(3)  With respect to PSUs, the treatment of such awards in the event of the named executive officer's death or permanent disability is described elsewhere in this proxy statement under the caption Treatment of Equity in the Event of Death or Permanent Disability and in footnote 4 to this table.

(3)

With respect to an involuntary termination of employment without cause or a constructive termination, includes the value of the payment of an additional amount equal to six months of base salary for all named executive officers (other than Mr. Mallon) in the event he or she does not obtain full-time employment within six months following the one year anniversary of his or her termination date.

(4)

With respect to options, reflects the in-the-money value of the unvested portion of such named executive officer's options that have vesting provisions based solely on time, and not performance milestones, and that would be accelerated, in each case, in accordance with the terms of our severance agreements with each executive officer. The value is calculated by multiplying the amount (if any) by which $13.31,$11.39, the closing price of our Class A common stock on the Nasdaq Global Select Market on December 31, 2019,2020, exceeds the exercise price of the option by the number of shares subject to the accelerated portion of the option.

With respect to RSUs, the value is calculated by multiplying the number of unvested RSUs with vesting provisions based solely on time that would be accelerated (if any) by $13.31,$11.39, the closing price of our Class A common stock on the Nasdaq Global Select Market on December 31, 2019,2020, in each case, in accordance with the terms of our severance arrangements with each executive officer.

With respect to PSUs, the value in the case of a change of control termination is calculated by multiplying the number of unvested and unearned PSUs that would be accelerated (if any) by $11.39, the closing price of our Class A common stock on the Nasdaq Global Select Market on December 31, 2020, as described in further detail above under the caption Treatment of PSUs in the Event of a Change of Control. In the case of a qualifying termination or death prior to a change of control, the PSUs will remain eligible to vest based on the attainment of the applicable performance goals, subject to applicable proration, as described above under the captions Severance Benefits not in Connection with a Change of Control and Treatment of Equity in the Event of Death or Permanent Disability. The values in this table assume that the PSUs will become earned at target.

(5)

Includes outplacement assistance benefits and subsidized COBRA benefits. With respect to involuntary termination without cause or a constructive termination, includes the value of the payment of an additional amount equal to six months of subsidized COBRA benefits for all named executive officers (other than Mr. Mallon) in the event he or she is not eligible to participate in the group medical plan of another employer following the one year anniversary of his or her termination date.

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CEO Pay Ratio

Under the Dodd-Frank Wall Street Reform and Consumer Protection Act, we are required to disclose the median of the annual total compensation of our employees, the annual total compensation of our principal executive officer on December 31, 2020, Mr. Mallon, and the ratio of these two amounts.

Both Dr. Hecht and Mr. Mallon served as our chief executive officer during fiscal year 2019. In accordance with Instruction 10 to Item 402(u) of Regulation S-K, we have elected to use Mr. Mallon's compensation for purposes of this pay ratio disclosure as Mr. Mallon was serving as our chief executive officer on December 31, 2019, the date selected by us to identify our median employee. Although we used Mr. Mallon's total 2019 compensation as reported in theSummary Compensation Table for the purposes of this pay ratio disclosure, due to certain one-time cash and equity awards granted to compensate Mr. Mallon, in part, for outstanding equity he forfeited by leaving his previous employer, Mr. Mallon's 2019 compensation is not representative of our expectations for Mr. Mallon's annual compensation on a go-forward basis. For purposes of computing Mr. Mallon's compensation for this pay ratio disclosure, we did not annualize the base salary paid to Mr. Mallon for the period in 2019 in which he served as our chief executive officer because his salary was unchanged from the salary his received in 2019 as a senior advisor to our board of directors. Moreover, the cash bonus paid to Mr. Mallon in 2020, for 2019 performance was not pro-rated for the period of service as our chief executive officer because Mr. Mallon was employed by Ironwood throughout 2019.

For 2019, our last completed fiscal year:

•

The estimated median of the annual total compensation of all employees of our company (other than Mr. Mallon) was $202,151;$222,011; and



•

Mr. Mallon's annual total compensation, as reported in theSummary Compensation Table included elsewhere in this proxy statement, was $10,068,800.$6,821,113.

Based on this information for 2019,2020, we estimate that the ratio of the annual total compensation of Mr. Mallon to the median annual total compensation of all employees was 50approximately 31 to 1. We believe this pay ratio is a reasonable estimate calculated in a manner consistent with SEC rules based on our payroll and employment records, and the methodology described below. Because the SEC rules for identifying the median of the annual total compensation of our employees and calculating the pay ratio based on that employee's annual total compensation allow companies to adopt a variety of methodologies, to apply certain exclusions, and to make reasonable estimates and assumptions that reflect their employee populations and compensation practices, the pay ratio reported by other companies may not be comparable to the pay ratio for Ironwood, as other companies have employees based in different locations (including other countries), have different business models and employee needs, have different employee populations and compensation practices and may utilize different methodologies, exclusions, estimates and assumptions in calculating their pay ratios.

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To identify the median of the annual total compensation of all our employees, as well as to determine the annual total compensation of our median employee and Mr. Mallon, we took the following steps:

•

As a result of significant changes to our employee population in 2019 on account of the Separation, weWe determined that it was appropriate to update the methodology by which we determinere-identify our median employee and to re-identify our median employee.for the purposes of the pay ratio disclosure for 2020. We determined that, as of December 31, 2019,2020, our employee population consisted of 317 individuals, with all of these individuals located in the United States.305 individuals. This population consisted of our full- and part-time employees. We useutilized a December 31, 2019 as an2020 identification date becauseas it is close to the date ofconsistent with our annual proxy statement filing and is consistent withCEO pay ratio reporting last year, our year-end financial reporting, and other reporting dates used in this proxy statement. Using aThe year-end identification date also enables us to make such identification in a reasonably efficient and economical manner.



•

To identify the "median employee" from our employee population, we determined to use the dollar value of total compensation, as defined in Item 402(c)(2)(x) of Regulation S-K, as our consistently applied compensation measure. To calculate the dollar value of total compensation, we started with the gross earnings of our employees as reflected in our payroll records for 20192020 as of the identification date, and as reportable to the Internal Revenue Service on Form W-2. We subtracted 20192020 equity earnings from stock option exercises and RSUstock award vesting and replaced them with the grant-date fair value of equity awards granted in 2019.2020. We subtracted 20182019 annual bonuses (paid in 2019)2020) and replaced them with 20192020 annual bonus awards (paid in 2020)2021). We also added the company's 401(k) matching contribution and included all other amounts reported pursuant to Item 402(c)(2)(ix) of Regulations S-K.contribution. For employees hired during 2019,2020, we annualized base salary and 20192020 bonus amounts, but not the value of equity granted in 20192020 as new hire awards are made on a one-time basis.

Since all our employees are located in the United States, as is Mr. Mallon, weWe did not make any cost-of-living adjustments in identifying the "median employee."

Once we identified the median employee, for purposes of the pay ratio, we calculated his or her compensation in the same manner as we do for Summary Compensation Table purposes.

•

With respect to the annual total compensation of our CEO, we used the amount reported in the "Total" column of theSummary Compensation Table for 2019.2020.

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2020  Proxy Statement    6364    Ironwood

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Compensation Committee Report

We have:

1.

reviewed and discussed with management theCompensation Discussion and Analysis found herein; and

2.

based on the review and discussions referred to in paragraph (1) above, we recommended to the board of directors that theCompensation Discussion and Analysis be included in the company's proxy statement on Schedule 14A for filing with the SEC.

		By the Compensation and HR Committee,
		Andrew Dreyfus, Chair Jon R. Duane Marla L. Kessler

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Proposal No. 2

At our 20202021 annual meeting, we are providing our stockholders with the opportunity to cast an advisory (non-binding) vote on named executive officer compensation, or a "say-on-pay" vote. This is a non-binding vote on the compensation of our "named executive officers," as described in theCompensation Discussion and Analysis section, the tabular disclosure regarding such compensation, and the accompanying narrative disclosure, all as set forth in this proxy statement.

The objective of our compensation policies is to provide compensation and incentives that align employee actions and motivations with the interests of our stockholders; attract, retain, motivate and reward outstanding talent across Ironwood through well-communicated programs that are aligned with our vision and mission; and support a positive company culture. In 2019,2020, the compensation program for our named executive officers consisted principally of base salary, cash bonus and long-term equity incentive compensation in the form of performance-based restricted stock optionsunits and restricted stock units. While we offer reasonably competitive base salaries and cash bonuses, our compensation program is weighted toward long-term equity incentive compensation as opposed to short-term or cash-based compensation. We believe this better aligns the interests of our named executive officers and our stockholders and serves to further focus our named executive officers on the creation of long-term stockholder value. If we achieve our corporate goals over the long term, we expect our stock price to reflect our performance and the equity awards currently held by our named executive officers to become an even more significant component of overall compensation. Our compensation and HR committee and board believes that this approach to executive compensation links compensation directly to continuous improvements in corporate performance and, ultimately our stock price, and demonstrates our "pay for performance" compensation philosophy.

Our previous say-on-pay vote was at our 20192020 annual meeting and was approved by approximately 87%84% of the votes cast on such matter. Under the Dodd-Frank Wall Street Reform and Consumer Protection Act, as well as the provisions of Section 14A of the Exchange Act, we must hold the advisory (non-binding) vote on named executive officer compensation at least once every three years. Based on the recommendation of our stockholders in 2017, our board of directors determined to provide our stockholders the opportunity to vote (on an advisory basis) on named executive officer compensation on an annual basis to allow our stockholders to provide us with regular, timely and direct input on our executive compensation philosophy, policies and practices as disclosed in the proxy statement each year. We believe this practice allows us to further align our compensation programs with our stockholders' interests as stockholder feedback may be taken into consideration as part of the compensation review process.

Vote Required

Because this proposal seeks a non-binding, advisory vote, there is no "required vote" that would constitute approval. However, our board of directors, including our compensation and HR committee, values the opinions of our stockholders and, to the extent there are a substantial number of votes cast against the executive officer compensation as disclosed in this proxy statement, we will consider our stockholders' concerns and evaluate which actions may be appropriate to address those concerns. Broker nominees do not have discretion to vote on this proposal without your instruction; if you do not instruct your broker nominee how to vote on this proposal, your broker nominee will not vote your shares with respect to this proposal. Any shares that are not voted, whether by abstention, broker non-votes or otherwise, will not affect the outcome of this proposal.

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Our Stockholders

Security Ownership of Certain Beneficial Owners and Management

The following table sets forth certain information with respect to the beneficial ownership of our Class A common stock at March 31, 20202021 for:

•

each person whom we know beneficially owns more than five percent of our Class A common stock;



•

each of our directors;



•

each of our named executive officers; and



•

all of our current directors and executive officers as a group.

The number of shares beneficially owned by each stockholder is determined under rules issued by the SEC. Under these rules, beneficial ownership includes any shares as to which the individual or entity has sole or shared voting power or investment power. Each of the stockholders listed has sole voting and investment power with respect to the shares beneficially owned by the stockholder unless noted otherwise, subject to community property laws where applicable.

The percentage of Class A common stock beneficially owned by each person is based on 159,368,126161,931,012 shares of Class A common stock outstanding on March 31, 2020.2021. Shares of Class A common stock that may be acquired within 60 days following March 31, 20202021 pursuant to the exercise of options or the vesting of RSUs, are included in the holdings of each stockholder, as applicable, and are deemed to be outstanding for the purpose of computing the percentage ownership of such holder. Such amounts, however, are not included in the holdings of any other stockholder in the table below and are not deemed to be outstanding for computing the percentage ownership of any other holder shown in the table below. Beneficial ownership representing less than one percent is denoted with an "*."

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2020  Proxy Statement    6768    Ironwood

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Unless otherwise indicated, the address for each of the stockholders in the table below is c/o Ironwood Pharmaceuticals, Inc., 100 Summer Street, Suite 2300, Boston, Massachusetts 02110.

​	​	​	​	​	​
Name of Beneficial Owner			Number of Shares of our Class A Common Stock		Percentage
​	​	​	​	​	​
Named Executive Officers and Directors		​
Mark Mallon(1)			275,129		*
Peter M. Hecht(2)		​	5,285,772		3.3%
Gina Consylman(3)			257,100		*
Halley E. Gilbert(4)		​	779,295		*
Thomas A. McCourt(5)			1,088,479		*
Andrew Dreyfus		​	86,938		*
Mark G. Currie(6)			1,374,124		*
Julie H. McHugh		​	109,337		*
Lawrence S. Olanoff			58,259		*
Edward P. Owens		​	182,234		*
Jon R. Duane			25,701		*
Marla L. Kessler		​	25,701		*
Catherine Moukheibir			25,701		*
All current executive officers and directors as a group (14 persons)(7)		​	3,843,894		2.4%
​	​	​	​	​	​
5% Security Holders
Wellington Management Group LLP(8)		​	21,777,701		13.7%
Brown Capital Management, LLC(9)			17,901,053		11.2%
The Vanguard Group(10)		​	16,638,941		10.4%
BlackRock, Inc.(11)			13,541,545		8.5%
Sarissa Capital Management LP(12)		​	12,493,000		7.8%
FMR LLC (Fidelity)(13)			11,353,494		7.1%
UBS Group AG(14)		​	11,181,451		7.0%
Janus Henderson Group PLC(15)			8,289,895		5.2%
​	​	​	​	​	​

​	​	​	​	​	​
Name of Beneficial Owner			Number of Shares of our Class A Common Stock		Percentage
​	​	​	​	​	​
Named Executive Officers and Directors		​
Mark Mallon(1)			449,356		*
Gina Consylman(2)		​	363,076		*
Thomas McCourt(3)			1,201,420		*
Jason Rickard(4)		​	306,016		*
Michael Shetzline, M.D., Ph.D.(5)			72,505		*
Mark G. Currie, Ph.D.(6)		​	1,352,404		*
Andrew Dreyfus			109,097		*
Jon R. Duane		​	47,421		*
Marla L. Kessler			47,421		*
Julie H. McHugh		​	125,607		*
Catherine Moukheibir			48,994		*
Lawrence S. Olanoff, M.D., Ph.D.		​	68,629		*
Edward P. Owens			218,954		*
Alexander J. Denner, Ph.D.(7)		​	16,429,079		10.1%
Jay P. Shepard			35,557		*
All current executive officers and directors as a group (14 persons)(8)		​	20,426,180		12.6%
​	​	​	​	​	​
5% Security Holders
Wellington Management Group LLP(9)		​	21,653,549		13.4%
Brown Capital Management, LLC(10)			20,150,463		12.4%
Sarissa Capital Management LP(11)		​	16,390,000		10.1%
The Vanguard Group(12)			15,892,347		9.8%
BlackRock, Inc.(13)		​	13,044,650		8.1%
Westfield Capital Management Company, LP(14)			8,488,043		5.2%
​	​	​	​	​	​

(1)

Includes (i) 205,260333,547 shares of Class A common stock issuable to Mr. Mallon upon the exercise of options that are exercisable within 60 days following March 31, 2020 and (ii) 51,719 restricted stock units that vest on May 7, 2020.

2021.

(2)

Includes 3,068,406 shares of Class A common stock issuable to Dr. Hecht upon the exercise of options that are exercisable within 60 days following March 31, 2020.

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(3)  Includes 187,948249,747 shares of Class A common stock issuable to Ms. Consylman upon the exercise of options that are exercisable within 60 days following March 31, 2020.

(4)  Includes 639,572 shares of Class A common stock issuable to Ms. Gilbert upon the exercise of options that are exercisable within 60 days following March 31, 2020.

(5)  2021.

(3)

Includes (i) 1,019,4371,094,150 shares of Class A common stock issuable to Mr. McCourt upon the exercise of options that are exercisable within 60 days following March 31, 20202021 and (ii) 5,713 restricted stock units that vest on May 7, 2020.20, 2021.

(4)

Includes (i) 171,600 shares of Class A common stock issuable to Mr. Rickard upon the exercise of options that are exercisable within 60 days following March 31, 2021 and (ii) 1,714 restricted stock units that vest on May 20, 2021.

(5)

Includes (i) 54,074 shares of Class A common stock issuable to Dr. Shetzline upon the exercise of options that are exercisable within 60 days following March 31, 2021 and (ii) 6,914 restricted stock units that vest on May 20, 2021.

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(6)

Includes 824,582 shares of Class A common stock issuable to Dr. Currie upon the exercise of options that are exercisable within 60 days following March 31, 2020.

2021.

(7)

Includes (i) 2,461,45039,079 shares of Class A common stock held directly by Dr. Denner and (ii) 16,390,000 shares of Class A common stock held by Sarissa Capital Management LP, or Sarissa. See note 11 below for information regarding the shares of Class A common stock held by Sarissa.

(8)

Includes (i) 2,394,423 shares of Class A common stock issuable upon the exercise of options that are exercisable within 60 days following March 31, 20202021 and (ii) 61,54714,341 restricted stock units that vest on May 7, 2020.

(8)  20, 2021.

(9)

Based upon the information provided by Wellington Management Group LLP, or Wellington, Wellington Group Holdings LLP, or Wellington Group, Wellington Investment Advisors Holdings LLP, or Wellington Investment, and Wellington Management Company LLP, or Wellington Management and, collectively with Wellington, Wellington Group and Wellington Investment, the Wellington Entities, in a Schedule 13G/A filed on January 28, 2020,February 4, 2021, reporting as of December 31, 2019.2020. According to this Schedule 13G/A, (i) Wellington hasdoes not have sole voting andor sole dispositive power with respect to noneany of these shares, and has shared voting power with respect to 20,301,61820,061,000 of these shares and shared dispositive power with respect to all of these shares, (ii) Wellington Group hasdoes not have sole voting andor sole dispositive power with respect to noneany of these shares, and has shared voting power with respect to 20,301,61820,061,000 of these shares and shared dispositive power with respect to all of these shares, (iii) Wellington Investment hasdoes not have sole voting andor sole dispositive power with respect to noneany of these shares, and has shared voting power with respect to 20,301,61820,061,000 of these shares and shared dispositive power with respect to all of these shares, and (iv) Wellington Management hasdoes not have sole voting andor sole dispositive power with respect to noneany of these shares, and has shared voting power with respect to 19,717,12819,476,837 of these shares and shared dispositive power with respect to 19,751,14419,509,866 of these shares. The address of the Wellington Entities is c/o Wellington Management Company LLP, 280 Congress Street, Boston, MA 02210.

(9)  

(10)

Based upon the information provided by Brown Capital Management, LLC, or Brown Capital, and The Brown Capital Management Small Company Fund, or Brown Capital Small Fund and, collectively with Brown Capital, the Brown Capital Entities, in a Schedule 13G/A filed on February 14, 2020,12, 2021, reporting as of December 31, 2019.2020. According to this Schedule 13G/A, (i) Brown Capital has sole voting power with respect 12,045,99612,680,378 of these shares, sole dispositive power with respect to all of these shares, and does not have shared voting power andor shared dispositive power with respect to noneany of these shares, and (ii) Brown Capital Small Fund has sole voting and sole dispositive power with respect to 9,980,218 of these shares and does not have shared voting andor shared dispositive power with respect to noneany of these shares. The address of the Brown Capital Entities is 1201 N. Calvert Street, Baltimore, MD 21202.

(10)  

(11)

Based upon the information provided by Sarissa and Dr. Denner in a Schedule 13D/A filed on March 1, 2021, reporting as of February 26, 2021, as well as a Form 4 filed on March 10, 2021, reporting as of March 10, 2021. According to this Schedule 13D/A, (i) Sarissa does not have sole voting or sole dispositive power with respect to any of these shares and has shared voting and shared dispositive power with respect to all of these shares, and (ii) Dr. Denner does not have sole voting or sole dispositive power with respect to any of these shares and has shared voting and shared dispositive power with respect to all of these shares. Does not include shares held directly by Dr. Denner, who is a member of our board of directors. The address of each of Sarissa and Dr. Denner is 660 Steamboat Road, Greenwich, CT 06830.

(12)

Based upon the information provided by The Vanguard Group, or Vanguard, in a Schedule 13G/A filed on February 12, 2020,10, 2021, reporting as of December 31, 2019.2020. According to this Schedule 13G/A, Vanguard hasdoes not have sole voting power with respect to 322,642any of these shares, and has sole dispositive power with respect to 16,309,20115,368,035 of these shares, shared voting power with respect to 24,865373,334 of these shares, and shared dispositive power with respect to 329,740524,312 of these shares. The address of Vanguard is 100 Vanguard Blvd., Malvern, PA 19355.

(11)  

(13)

Based upon the information provided by BlackRock, Inc., or BlackRock, in a Schedule 13G/A filed on February 5, 2020,January 29, 2021, reporting as of December 31, 2019.2020. According to this Schedule 13G/A, Blackrock has sole voting power with respect to 13,084,46312,844,041 of these shares, sole dispositive power with respect to all of these shares, and does not have shared voting andor shared dispositive power with respect to noneany of these shares. The address of BlackRock is 55 East 52nd Street, New York, NY 10055.

(12)  

(14)

Based upon the information provided by SarissaWestfield Capital Management Company, LP, or Sarissa, Alexander J. Denner, Ph.D., Sarissa Capital Offshore Master Fund LP, or Sarissa Capital Offshore, Sarissa Capital Catapult Fund LLC, or Sarissa Capital Catapult, Sarissa Capital Hawkeye Fund LP, or Sarissa Capital Hawkeye, and Sarissa Capital Athena Fund Ltd, or Sarissa Capital Athena and, collectively with Sarissa, Dr. Denner, Sarissa Capital Offshore, Sarissa Capital Catapult and Sarissa Capital Hawkeye, the Sarissa Holders,Westfield, in a Schedule 13D/A13G filed on February 26, 2020,January 7, 2021, reporting as of February 25,December 31, 2020. According to this Schedule 13D/A, (i) Sarissa has sole voting and sole dispositive power with respect to 1,357,215 of these shares and shared voting and shared dispositive power with respect to 11,135,785 of these shares, (ii) Dr. Denner has sole voting and sole dispositive power with respect to none of these shares and shared voting and shared dispositive power with respect to all of these shares, (iii) Sarissa Capital Offshore has sole voting and sole dispositive power with respect to 5,682,660 of these shares and shared voting and shared dispositive power with respect to none of these shares, (iv) Sarissa Capital Catapult has sole voting and sole dispositive power with respect to 1,948,655 of these shares and shared voting and shared dispositive power with respect to none of these shares, (v) Sarissa Capital Hawkeye has sole voting and sole dispositive power with respect to 1,465,765 of these shares and shared voting and shared dispositive power with respect to none of these shares, and (vi) Sarissa Capital Athena has sole voting and sole dispositive power with respect to 2,038,705 of these shares and shared voting and shared dispositive power with respect to none of these shares, The address of the Sarissa Holders is c/o Sarissa Capital Management LP, 660 Steamboat Road, Greenwich, CT 06830.

(13)  Based upon the information provided by FMR LLC, or FMR, and Abigail P. Johnson in a Schedule 13G/A filed on February 7, 2020, reporting as of December 31, 2019. According to this Schedule 13G/A, (i) FMR13G, Westfield has sole voting power with respect to 2,874,9777,660,852 of these shares, sole dispositive power with respect to all of these shares, and neitherdoes not have shared voting noror shared dispositive power with respect to these shares, and (ii) Ms. Johnson has neither sole nor shared voting power with respect to these shares, sole dispositive power with respect to all of these shares, and shared dispositive power with respect to noneany of these shares. The address of FMR and Ms. JohnsonWestfield is 245 Summer Street,1 Financial Center, Boston, MA 02210.

(14)  Based upon the information provided by UBS Group AG, or UBS, in a Schedule 13G/A filed on February 12, 2020, reporting as of December 31, 2019. According to this Schedule 13G, UBS has sole voting power with respect to 9,912,172 of these shares, shared dispositive power with respect to all of these shares, and shared voting power and sole dispositive power with respect to none of these shares. The address of UBS is Bahnhofstrasse 45, Zurich, Switzerland.

(15)  Based upon the information provided by Janus Henderson Group PLC, or Janus, in a Schedule 13G filed on February 14, 2020, reporting as of December 31, 2019. According to this Schedule 13G, Janus has sole voting and sole dispositive power with respect to none of these shares and shared voting and shared dispositive power with respect to all of these shares. The address of Janus is c/o Janus Henderson Group plc, 201 Bishopsgate EC2M 3AE, United Kingdom.

02111.

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2020  Proxy Statement    6970    Ironwood

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Certain Relationships and
Related Person Transactions

Since January 1, 2019,2020, except as described below, there has not been, nor is there currently proposed, any transaction or series of similar transactions to which we were or are a party in which the amount involved exceeded or exceeds $120,000 and in which any of our directors, executive officers, holders of more than 5% of any class of our voting securities, or any member of the immediate family of any of the foregoing persons, had or will have a direct or indirect material interest, other than compensation arrangements with directors and executive officers, which, with respect to our directors and named executive officers are described under the captionsOur Board of Directors—How We Are Paid andExecutive Compensation appearing elsewhere in this proxy statement.

Indemnification Agreements

We have entered into indemnification agreements with each of our current directors and certain of our officers. These agreements require us to indemnify these individuals to the fullest extent permitted under Delaware law against liabilities that may arise by reason of their service to us and to advance expenses incurred as a result of any proceeding against them as to which they could be indemnified. We intend to enter into indemnification agreements with our future directors and executive officers.

The Separation

On April 1, 2019, we completed the Separation. The Separation was effected by means of a distribution of all of the outstanding shares of common stock of Cyclerion through a dividend in-kind of Cyclerion's common stock, with no par value, to our stockholders of record as of the close of business on March 19, 2019. In connection with the Separation, we and Cyclerion entered into certain agreements that effected the separation of Cyclerion's business from us and govern our relationship with Cyclerion after the Separation. The following is a summary of the terms of the material agreements that we have entered into with Cyclerion in connection with the Separation. Dr. Hecht, our former chief executive officer, is chief executive officer of Cyclerion and Dr. Currie, our former senior vice president, chief scientific officer and president of R&D is currentlyand current member of our board of directors, was president and chief scientific officer of Cyclerion as well asin 2020 and is currently a member of our board of directors.senior advisor to Cyclerion.

Separation Agreement

In connection with the Separation, Ironwood entered into a separation agreement with Cyclerion, dated as of March 30, 2019, that, among other things, set forth our agreements with Cyclerion regarding the principal actions to be taken in connection with the Separation, including the distribution detailed above. The separation agreement identified assets to be transferred, liabilities to be assumed and contracts to be assigned to each of Ironwood and Cyclerion as part of the Separation, and it provided for when and how these transfers, assumptions and assignments would occur. The separation agreement was intended to provide for those transfers of assets and assumptions of liabilities that were necessary so that after the Separation, Ironwood and Cyclerion would have the assets necessary to operate their respective businesses and retain or assume the liabilities related to those assets. Each of Ironwood and Cyclerion agreed to releases, with respect to pre-distribution claims, and cross indemnities, with respect to post-distribution claims, that, except as otherwise provided in the separation agreement, were principally designed to place financial responsibility for the obligations and liabilities allocated to Ironwood under the separation agreement with Ironwood and financial responsibility for the obligations and liabilities allocated to Cyclerion under the separation agreement with Cyclerion.

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Ironwood and Cyclerion are also were each subject to two-year non-solicit and non-hire restrictions.restrictions, which ended on April 1, 2021. In addition, the parties agreed to certain non-competition restrictions, including Ironwood's agreement not to engage, for three years following the Separation, in the business of discovering, researching, developing, importing, exporting, manufacturing, marketing, distributing, promoting or selling any pharmaceutical product (a) for the diagnosis, prevention or treatment of diabetic nephropathy, heart failure with preserved ejection fraction or sickle cell disease or (b) that contains one or more soluble guanylate cyclase, or sGC, stimulators.

Development Agreement

We entered into a development agreement with Cyclerion pursuant to whichwhereby Cyclerion providesprovided us with certain research and development services with respect to certain of our products and product candidates, including without limitation MD-7246 (linaclotide delayed release) and IW-3718. Such research and development activities arewere governed by a joint steering committee comprised of representatives from both Cyclerion and Ironwood. We paypaid Cyclerion fees for such research and development services as mutually agreed upon by us and Cyclerion as provided under this development agreement with certain allowances for specified overages. As ofThis agreement terminated effective March 31, 2020, we have2021. We incurred approximately $5.5$6.9 million under this agreement.

Transition Services Agreements

Ironwood Transition Services

Prior to the Separation, we provided Cyclerion with significantcertain corporate and shared services and resources related to corporate functions such as finance, human resources, internal audit, research and development, financial reporting and information technology, which we refer to collectively as the "Ironwood Services." Pursuant to this agreement, each of the Ironwood Services was to continue for an initial term of up to two years (as applicable), unless earlier terminated or extended according to the terms of the transition services agreement. We and Cyclerion agreed to terminate thisThis agreement terminated effective March 31, 2020. We earnedreceived approximately $313,000$313,428 in total fees for the Ironwood Services under this agreement, which fees were based on our cost of providing the Ironwood Services.

Cyclerion Transition Services

We also entered into a second transition services agreement whereby Cyclerion provided certain finance, procurement and facilities services to us, which we refer to herein collectively as the "Cyclerion Services." Pursuant to this agreement, each of the Cyclerion Services were available to us for a term of one year.year; this agreement terminated effective March 31, 2020. We incurredpaid approximately $105,000$105,060 in total fees for the Cyclerion Services under this agreement, which fees were based on Cyclerion's cost of providing the Cyclerion Services.

Intellectual Property License Agreement

We entered into an intellectual property license agreement with Cyclerion pursuant to which each party granted a license to the other party to certain know-how. We granted Cyclerion a perpetual, worldwide, non-exclusive, royalty-free, fully paid-up license to certain know-how to allow Cyclerion to use such know-how in connection with Cyclerion's ongoing and future research and development activities related to sGC stimulator products in any field. Cyclerion granted us a perpetual, worldwide, non-exclusive, royalty-free, fully paid-up license to certain know-how for use outside of the research and development of sGC stimulator products, including in our existing products and product candidates. Such licenses between the parties generally allow current or future uses of the know-how in connection with each party's respective fields.

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Tax Matters Agreement

We entered into a tax matters agreement with Cyclerion that governs Ironwood's and Cyclerion's respective rights, responsibilities and obligations with respect to taxes (including taxes arising in the ordinary course of business and taxes, if any, incurred as a result of any failure of the distribution of Cyclerion common stock to Ironwood stockholders and certain related transactions to qualify as tax-free for U.S. federal income tax purposes), tax attributes, the preparation and filing of tax returns, the control of audits and other tax proceedings and assistance and cooperation in respect of tax matters.

The tax matters agreement imposed certain restrictions on Cyclerion and its subsidiaries (including restrictions on share issuances, business combinations, sales of assets and similar transactions) designed to preserve the tax-free status of the distribution and certain related transactions. The tax matters agreement also provided special rules that allocate tax liabilities in the event the distribution, together with certain related transactions, is not tax-free. In general, under the tax matters agreement, each party is expected to be responsible for any taxes imposed on Ironwood or Cyclerion that arise from the failure of the distribution, together with certain related transactions, to qualify as a transaction that is generally tax-free, for U.S. federal income tax purposes, under Sections 355 and 368(a)(1)(D) and certain other relevant provisions of the Code, to the extent that the failure to so qualify is attributable to an acquisition of stock or assets of, or certain actions, omissions or failures to act of, such party. If both Cyclerion and Ironwood are responsible for such failure, liability will be shared according to relative fault. U.S. tax otherwise resulting from the failure of the distribution, together with certain related transactions, to qualify as a transaction that is tax-free generally is the responsibility of Ironwood.

Employee Matters Agreement

We entered into an employee matters agreement with Cyclerion, which allocated assets, liabilities and responsibilities relating to the employment, compensation, and employee benefits of Ironwood and Cyclerion employees, and other related matters in connection with the Separation, including the treatment of outstanding incentive equity awards and certain retirement and welfare benefit obligations. The employee matters agreement generally provided that, unless otherwise specified, Cyclerion is responsible for liabilities associated with employees who transferred to Cyclerion and employees whose employment terminated prior to the Separation but who primarily supported the Cyclerion business, whether incurred prior to or after the Separation, and Ironwood is responsible for liabilities associated with other employees, including employees retained by Ironwood.

The Private Placement

On February 25, 2019, Cyclerion, which was Ironwood's wholly owned subsidiary at the time, and various investors entered into an amended and restated common stock purchase agreement pursuant to which these investors agreed to make an aggregate cash investment in Cyclerion. These investors included the following, each of whom was either an Ironwood director, an Ironwood executive officer, an immediate family member of an Ironwood director or executive officer, an entity related to such a director, executive officer or immediate family member, or beneficially owned at least 5% of Ironwood's Class A common stock: accounts managed by direct or indirect subsidiaries of FMR LLC, a donor advised fund created by Dr. Hecht, Dr. Currie and certain members of Dr. Hecht's immediate family, including through a trust or donor advised fund. Pursuant to this agreement, accounts managed by direct or indirect subsidiaries of FMR LLC agreed to invest up to $17,500,004, the donor advised fund created by Dr. Hecht agreed to invest up to $34,000,000, Dr. Currie agreed to invest up to $4,000,000 and Dr. Hecht's immediate family agreed to invest up to $6,800,000 in the aggregate. This investment closed on April 2, 2019.

Procedures for Related Party Transactions

Under our code of business conduct and ethics, our employees, officers and directors are discouraged from entering into any transaction that may create or give the appearance of a conflict of interest. In addition, they must report any potential conflict of interest, including related party transactions, to certain members of our management or the chair of our audit committee. Pursuant to its charter, our audit committee must approve any related party transactions, including those transactions involving our directors. In approving or rejecting a proposed transaction, the audit committee considers the relevant facts and circumstances available to and deemed relevant by the audit committee, including the material terms of the transaction, risks, benefits, costs, availability of other comparable services or

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products and, if applicable, the impact on a director's independence. Our audit committee will approve only those transactions that, in light of known circumstances, are in, or are not inconsistent with, our best interests, as our audit committee determines in the good faith exercise of its discretion. A copy of our code of business conduct and ethics and our audit committee charter are available through the Investors section of our website atwww.ironwoodpharma.com, under the heading Corporate Governance.

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Proposal No. 3

Our audit committee has appointed Ernst & Young LLP to serve as our auditors for the fiscal year ending December 31, 2020.2021. The firm of Ernst & Young LLP, an independent registered public accounting firm, has audited the books and accounts of Ironwoodserved as Ironwood's auditor since 1998 and has audited our financial statements for the years ended December 31, 2020, 2019 2018 and 2017.2018. Detailed disclosure of the audit, audit-related, tax and other fees we paid tobilled for services rendered by Ernst & Young LLP in 20192020 and 20182019 are set forth below. Based on these disclosures and information in the audit committee report on page 1719 of this proxy statement, our audit committee is satisfied that our auditors are sufficiently independent of management to perform their duties properly. Although not legally required to do so, our board of directors considers it desirable to seek, and recommends, stockholder ratification of its selection of auditors for fiscal year 2020.2021.

Representatives of Ernst & Young LLP are expected to attend the virtual annual meeting to answer any questions and they will have the opportunity to make a statement if they wish.

The table below presents aggregate fees for professional audit services rendered by Ernst & Young LLP for the years ended December 31, 2019 and 2018 for the audits of our annual financial statements for the years ended December 31, 2020 and 2019 and fees billed for other services rendered by Ernst & Young LLP during those periods. It is the audit committee's policy that all audit and non-audit services to be performed by Ernst & Young LLP be pre-approved. The audit committee annually reviews and pre-approves the permissible services that may be provided by Ernst & Young LLP to assure the provision of such services does not impair the auditor's independence. In accordance with the pre-approval policy, our management informs the audit committee of each service performed by Ernst & Young LLP pursuant to the pre-approval policy. Requests to provide services that require separate approval by the audit committee are submitted to the audit committee or its designee by both our chief financial officer, or chief accounting officer or controller and Ernst & Young LLP. All of the services described in the following fee table were approved in conformity with the audit committee's pre-approval policy.

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			2019			2018				2020			2019
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Audit		$	1,840,900		$	994,154			$	1,372,342		$	1,840,900
Audit-related		$	—		$	1,564,161			$	—		$	—
Tax		$	—		$	—			$	—		$	—
All other		$	1,735		$	6,910			$	6,860		$	1,735
​		$	1,842,635		$	2,565,225			$	1,379,202		$	1,842,635
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Audit fees for 20192020 and 20182019 were for professional services rendered for the audits of our financial statements and internal controls over financial reporting, including accounting consultation,consultations and reviews of quarterly financial statements, as well as for services that are normally provided in connection with regulatory filings or engagements, including auditor consents. Additionally we incurred approximately $198,000 of audit fees related to the Separation which were reimbursed by Cyclerion pursuant to the Tax Matters Agreement. Audit fees for 20192020 were significantly higherlower than they were in 20182019 due to services provided in 2019 in connection with the Separation, including the review and/or audit of discontinued operations, as well as accounting review of certain collaboration and co-promotion agreements and debt-related transactions.

Audit-related fees for 2018 were principally comprised of services provided in connection with the Separation, including the review and/or audit of Cyclerion carve-out financial statements, as well as accounting consultations associated with the anticipated adoption of new accounting standards.

Other services in 20192020 and 20182019 include license fees for a web-based accounting research tool.

Other than the foregoing, Ernst & Young LLP did not provide any other services to us in 20192020 or 2018.2019.

Vote Required

The approval of the proposal to ratify the selection of Ernst & Young LLP as our auditors requires a majority of the votes cast for or against the proposal. Because we believe this matter to be routine, a broker nominee may vote on your behalf if you do not otherwise provide instructions. As a result, we do not expect there will be any broker non-votes on this matter. Abstentions will not affect the outcome of this proposal.

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User's Guide

Our board of directors is soliciting proxies for the 20202021 annual meeting of stockholders. This proxy statement explains the agenda, voting information and procedures for the meeting. Please read it carefully. This proxy statement and related materials are first being made available to stockholders on or about April 21, 2020,22, 2021, and the notice of internet availability of proxy materials is first being sent to our stockholders on the same day. All stockholders will also have the ability to access the proxy materials online through the Investors section of our website atwww.ironwoodpharma.com, under the heading Featured Reports.Financial Information—SEC Filings.

Who can vote

Only stockholders of record of our Class A common stock at the close of business on April 13, 202012, 2021 can vote at the meeting.

Quorum

In order to hold and complete the business of the annual meeting, we must have a majority of the votes entitled to be cast represented at the meeting or by proxy. On our record date, April 13, 2020,12, 2021, we had 159,374,029161,935,176 shares of our Class A common stock outstanding and entitled to vote. With respect to all matters that will come before the meeting, each share is entitled to one vote.

Notice of internet availability of proxy materials

Pursuant to rules adopted by the SEC, we have elected to provide access to our proxy materials via the internet. Accordingly, we are sending a notice of internet availability of proxy materials to our stockholders. All stockholders will have the ability to access the proxy materials on the website referenced in the notice and to request to receive a printed set of the proxy materials by mail. Instructions on how to access the proxy materials over the internet and how to request a printed copy may be found in the notice. In addition, stockholders may request to receive proxy materials in printed form by mail or electronically by email on an ongoing basis. We encourage stockholders to take advantage of the availability of the proxy materials on the internet or through email to help reduce the environmental impact of our annual meetings.

Voting procedures—stockholders of record and beneficial owners

You are a stockholder of record if your shares of our stock are registered directly in your own name with our transfer agent, Computershare Trust Company, N.A., or Computershare. You are a beneficial owner if a brokerage firm, bank, trustee or other agent, called a "nominee," holds your stock. This is often called ownership in "street name" because your name does not appear in the records of Computershare. If you hold your shares in street name, you should receive a voting instruction form from your broker nominee.

How to vote your shares.

If you are a stockholder of record, there are four ways to vote:

•

Online Before the Meeting.  You may vote by proxy via the internet by following the instructions provided on the notice of internet availability of proxy materials or the proxy card. You must have the

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16-digit control number that is on either the notice of internet availability of proxy materials or the proxy card when voting.

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Online During the Meeting.  You may vote online during the annual meeting through the linkwww.virtualshareholdermeeting.com/IRWD2020IRWD2021. The 16-digit control number provided on your notice of internet availability of proxy materials or proxy card is necessary to access the website. The meeting will begin at 9:00 a.m. Eastern Time (with check-inlog-in beginning at 8:45 a.m. Eastern Time) on Wednesday, June 3, 2020.2, 2021.



•

By Telephone.  If you request printed copies of the proxy materials by mail and you live in the United States or Canada, you may vote by proxy by calling the toll-free number found on the proxy card. You must have the control number that is on the proxy card when voting.



•

By Mail.  If you request printed copies of the proxy materials by mail, you may vote by proxy by filling out the proxy card and sending it back in the envelope provided.

If you are a beneficial owner of shares held in street name, there are four ways to provide voting instructions:

•

Online Before the Meeting.  You may provide voting instructions via the internet by following the instructions provided on your voting instruction form. You must have the 16-digit control number that is on the voting instruction form when voting.



•

Online During the Meeting.  You may vote online during the annual meeting through the linkwww.virtualshareholdermeeting.com/IRWD2020IRWD2021. The 16-digit control number provided on your voting instruction form is necessary to access the website. The meeting will begin at 9:00 a.m. Eastern Time (with check-inlog-in beginning at 8:45 a.m. Eastern Time) on Wednesday, June 3, 2020.2, 2021.



•

By Telephone.  You may provide voting instructions by calling the toll-free number found on your voting instruction form. You must have the control number that is on the voting instruction form when voting.



•

By Mail.  You may provide voting instructions by filling out the voting instruction form and sending it back in the envelope provided.

How you may revoke your proxy or voting instructions.    If you are a stockholder of record, you may revoke or amend your proxy before it is voted at the annual meeting by writing to us directly in a timely manner "revoking" your earlier proxy, submitting a new proxy in a timely manner with a later date by mail, over the telephone or on the internet, or by attending the meeting and voting. Your last dated proxy timely received prior to or vote cast at the annual meeting will be counted.

What if you receive more than one notice of internet availability of proxy materials, proxy card or voting instruction form?    This means that you may have more than one account at Computershare and/or with a nominee. Your notice of internet availability of proxy materials, proxy card or voting instruction form lists the number of shares you are voting. Please vote the shares on all notices of internet availability of proxy materials, proxy cards and voting instruction forms that you receive.

We recommend you consolidate your holdings under the same name, address and tax identification number, if possible. This will eliminate some duplication of mailings and reduce costs. Please contact your nominee to consolidate accounts, or our transfer agent, Computershare, at (800) 368-5948, as applicable.

Householding of proxy materials.    SEC rules concerning the delivery of proxy materials allow us or your broker to send a single notice or, if applicable, a single set of our proxy materials to any household at which two or more of our stockholders reside, if we or your broker believe that the stockholders are members of the same family, unless we have received contrary instructions from one or more of the stockholders. This practice, referred to as "householding," benefits both you and us. It reduces the volume of duplicate information received at your

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household and helps to reduce our expenses. The rule applies to our notices, annual reports, proxy statements and information statements.

We will undertake to deliver promptly, upon written request, a separate copy to a stockholder at a shared address to which a single copy of the notice of internet availability of proxy materials was delivered. You may make a written request by sending a notification to our Secretary at the address below, providing your name, your shared address, and the address to which we should direct the additional copy of the notice of internet availability of proxy materials. Multiple stockholders sharing an address who have received one copy of a mailing and would prefer us to mail each stockholder a separate copy of future mailings should contact us at the below address, as well. Additionally, if current stockholders with a shared address received multiple copies of a mailing and would prefer us to mail one copy of future mailings to stockholders at the shared address, notification of that request may also be sent to us at the below address. Stockholders who participate in householding will continue to have access to and utilize separate proxy voting instructions.

Any request relating to receipt of proxy materials should be sent to: Secretary, Ironwood Pharmaceuticals, Inc., 100 Summer Street, Suite 2300, Boston, Massachusetts 02110.

Abstentions and "broker non-votes." If you are a stockholder of record and you vote "abstain" or "withhold" on any matter, your shares will not be voted on that matter and will not be counted as votes cast in the final tally of votes on that matter. However, your shares will be counted for purposes of determining whether a quorum is present. If you are a beneficial owner holding shares through a broker nominee, you may instruct your broker nominee that you wish to abstain from voting on a proposal or withhold authority to vote for one or more nominees for director.

A broker nominee generally may not vote on "non-routine" matters without receiving your specific voting instructions. A "broker non-vote" occurs when a broker nominee holding shares in street name votes shares on some matters at the meeting but not others. Like abstentions, broker non-votes are counted as present and entitled to vote for quorum purposes, but are not counted as votes cast. AtBroker nominees who hold shares for the accounts of their clients have discretionary authority to vote shares if specific instructions are not given with respect to routine matters. Although the determination of whether a broker nominee will have discretionary voting power for a particular item is typically determined only after proxy materials are filed with the SEC, we expect that at the annual meeting of stockholders your broker nominee will not be able to submit a vote on the election of directors or the advisory votes on named executive officer compensation unless it receives your specific instructions. If your broker nominee does not receive your specific instructions, for these proposals, itbut will submit a broker non-vote. The broker nominee will, however, be able to vote on the ratification of the selection of our independent auditors even if it does not receive your instructions. As a result, if your broker nominee does not receive your specific instructions so we dofor these proposals, it will submit a broker non-vote on the election of directors or the advisory votes on named executive officer compensation and may vote on the ratification of the selection of our independent auditors even if it does not expect any broker non-votes will exist in connection with such proposal.receive your instructions.

Discretionary authority.    If you are a stockholder of record and you properly submit your proxy card without making any specific selections, your shares will be voted on each matter before the annual meeting in the manner recommended by our board of directors. If other matters not included in this proxy statement properly come before the annual meeting, the persons named on the proxy card, or otherwise designated, will have the authority to vote on those matters for you as they determine, to the extent permitted by Rule 14a-4(c)(1) of the Exchange Act. If you are a beneficial owner of shares held in street name, please see the discussion above regarding broker non-votes and the rules related to voting by broker nominees.

Vote required

The required vote for each of the proposals expected to be acted upon at the annual meeting is described below.

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Proposal No. 1—Election of Class I and Class II Directors:
the threeThe seven nominees for director with the highest number of affirmative votes will be elected as directors to serve for one-year terms and until their successors are duly elected and qualified or until their death, resignation or removal. We expect that broker nominees will not have discretion to vote on this proposal without your instruction; if you do not instruct your broker nominee how to vote on this proposal, your broker nominee will deliver a broker non-vote. Because there is no minimum vote required, abstentions and broker non-votes will not affect the outcome of this proposal.

Proposal No. 2—Advisory (non-binding) Vote on Named Executive Officer Compensation, or "Say-on-Pay":
becauseBecause this proposal calls for a non-binding, advisory vote there is no "required vote" that would constitute approval. However, our board of directors, including our compensation and HR committee, values the opinions of our stockholders and, to the extent there are a substantial number of votes cast against the named executive officer compensation disclosed in this proxy statement, we will consider our stockholders' concerns and evaluate what actions may be appropriate to address those concerns. BrokerWe expect that broker nominees dowill not have discretion to vote on this proposal without your instruction; if you do not instruct your broker nominee how to vote on this proposal, your broker nominee will deliver a broker non-vote. Any shares that are not voted, whether by abstention, broker non-votes or otherwise, will not affect the outcome of this proposal.

Proposal No. 3—Ratification of Auditors:
theThe approval of this proposal requires a majority of the votes cast for or against the proposal. Abstentions and broker non-votes will not affect the outcome of this proposal. Further, because we believe this matter to be routine, a broker nominee may vote on your behalf if you do not otherwise provide instructions. As a result, we do not expect there will be any broker non-votes on this matter.

Results of the voting.    We expect to announce the preliminary voting results at the annual meeting. The final voting results will be tallied by the inspector of election and published in a Current Report on Form 8-K, which we are required to file with the SEC, within four business days following the annual meeting.

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Costs of solicitation and solicitation participants.    We will pay the costs of soliciting proxies. These costs also include support for the hosting of the virtual meeting. We will solicit proxies by email from stockholders who are our employees or who previously requested to receive proxy materials electronically. Our directors, our officers and our employees also may solicit proxies on our behalf, personally, electronically or by telephone, facsimile or mail or other means, without additional compensation. We may request that brokerage firms, banks and other agents forward proxy materials to beneficial owners and we would reimburse such institutions for their out-of-pocket expenses incurred.

We may also utilize the assistance of third parties in connection with our proxy solicitation efforts and we would compensate such third parties for their efforts. We have engaged one such third party, MacKenzie Partners, to assist in the solicitation of proxies and provide related advice and informational support, for service fees of up to $20,000$12,500 and the reimbursement of certain expenses.

Additional Meeting Information

We encourage you to access the meeting prior to the start time. Please allow sufficient time for online check-in,log-in, which begins at 8:45 a.m. Eastern Time. You may check your browser's compatibility any time prior to the meeting atwww.virtualshareholdermeeting.com/IRWD2020IRWD2021. If you want to submit a question you may do so electronically starting at the time of check-in or during the meeting.

If you have technical difficulties or trouble accessing the virtual meeting, there will be technicians ready to assist you. If you encounter any technical difficulties accessing the virtual meeting during the check-in or meeting time, please call the technical support number that will be posted on the virtual shareholderstockholder meeting log in page.

If you want to submit a question you may do so electronically starting at the time of check-in or during the meeting. We will post any appropriate questions received during the meeting and our answers in the Investors section of our website atwww.ironwoodpharma.com as soon as practical after the meeting.

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Stockholder Communications, Proposals
and Nominations for Directorships

Communications

A stockholder may send general communications to our board of directors, any committee of our board of directors or any individual director by directing such communication to General Counsel,Secretary, Ironwood Pharmaceuticals, Inc., 100 Summer Street, Suite 2300, Boston, Massachusetts 02110. All communications will be reviewed by our general counselSecretary and, if requested by the stockholder, forwarded to our board of directors or an individual director, as applicable. Our general counselSecretary reserves the right not to forward to our board of directors or any individual director any abusive, threatening or otherwise inappropriate materials.

Any request for materials or other communications directed to our secretary should be sent to: Secretary, Ironwood Pharmaceuticals, Inc., 100 Summer Street, Suite 2300, Boston, Massachusetts 02110.

Proposals and Nominations

Stockholders who wish to present a proposal for inclusion in our proxy materials for our 20212022 annual meeting should follow the procedures prescribed in Rule 14a-8 under the Exchange Act and our bylaws. Those procedures require that we receive a stockholder proposal in writing no later than December 22, 202023, 2021 in order for such proposal to be included in our proxy materials.

Under our bylaws, stockholders who wish to nominate a director or include a proposal in our 20212022 annual meeting of stockholders (but do not wish to include such proposal in our proxy materials) must give us timely notice. To be timely, a notice of director nomination or other proposal for the 20212022 annual meeting of stockholders must be received by us no earlier than March 5, 20214, 2022 and no later than April 4, 2021,3, 2022, unless the date of the 20212022 annual meeting of stockholders is more than 30 days from the anniversary date of the 20202021 annual meeting of stockholders, in which event the notice must be received by us on or before 15 days after the day on which the date of the 20212022 annual meeting of stockholders is first disclosed in a public announcement. The notice must contain specified information that is prescribed in our bylaws about you and the director nominee or the proposal, as applicable. If any director nomination or stockholder proposal is submitted after April 4, 2021,3, 2022, our bylaws provide that the nomination or the proposal shall be disregarded.

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SEC Filings

We file annual, quarterly and current reports, as well as other information with the SEC. You can obtain any of them from the SEC at its website atwww.sec.gov. The documents are also available from us without charge by requesting them in writing or by telephone from Ironwood Pharmaceuticals, Inc., 100 Summer Street, Suite 2300, Boston, Massachusetts 02110, Attention: Corporate Communications, telephone: (617) 621-7722, or by visiting the Investors section of our website atwww.ironwoodpharma.com.

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VOTE BY INTERNET Before The Meeting - Go to www.proxyvote.com You may use the Internet to transmit your voting instructions and for electronic delivery of information up until 11:59 P.M. Eastern Time the day before the meeting date. Have your proxy card in hand when you access the web site and follow the instructions to obtain your records and to create an electronic voting instruction form. IRONWOOD PHARMACEUTICALS, INC. 100 SUMMER STREET, SUITE 2300 BOSTON, MA 02110 During The Meeting - Go to www.virtualshareholdermeeting.com/IRWD2020IRWD2021 You may also vote during the meeting. Have the information that is printed in the box marked by the arrow available and follow the instructions. ELECTRONIC DELIVERY OF FUTURE PROXY MATERIALS If you would like to reduce the costs incurred by our company in mailing proxy materials, you can consent to receiving all future proxy statements, proxy cards and annual reports electronically via e-mail or the Internet. To sign up for electronic delivery, please follow the instructions above to vote using the Internet and, when prompted, indicate that you agree to receive or access proxy materials electronically in future years. VOTE BY PHONE - 1-800-690-6903 Use any touch-tone telephone to transmit your voting instructions up until 11:59 P.M. Eastern Time the day before the meeting date. Have your proxy card in hand when you call and then follow the instructions. VOTE BY MAIL Mark, sign and date your proxy card and return it in the postage-paid envelope we have provided or return it to Vote Processing, c/o Broadridge, 51 Mercedes Way, Edgewood, NY 11717. TO VOTE, MARK BLOCKS BELOW IN BLUE OR BLACK INK AS FOLLOWS: D14047-P36525D43110-P53341 KEEP THIS PORTION FOR YOUR RECORDS DETACH AND RETURN THIS PORTION ONLY THIS PROXY CARD IS VALID ONLY WHEN SIGNED AND DATED. IRONWOOD PHARMACEUTICALS, INC. The Board of Directors recommends you vote FOR the following: For Withhold For All AllAllExcept To withhold authority to vote for any individual nominee(s), mark "For All Except" and write the number(s) of the nominee(s) on the line below. ! !! 1. Election of Directors Nominees: Class I 01) 02) 03) Mark G. Currie, Ph.D. Alexander J. Denner, Ph.D. Jon R. Duane Mark MallonClass II 04) 05) 06) 07) Marla L. Kessler Catherine Moukheibir Lawrence S. Olanoff, M.D., Ph.D. Jay P. Shepard For Against Abstain The Board of Directors recommends you vote FOR the following proposals: ! ! ! ! ! ! 2. Approval, by non-binding advisory vote, of the compensation paid to the named executive officers. 3. Ratification of the selection of Ernst & Young LLP as the Company's independent registered public accounting firm for 2020.2021. NOTE: In their discretion, the Proxies are authorized to vote upon such other business as may properly come before the meeting or any adjournment or postponement thereof. Please sign exactly as your name(s) appear(s) hereon. When signing as attorney, executor, administrator, or other fiduciary, please give full title as such. Joint owners should each sign personally. All holders must sign. If a corporation or partnership, please sign in full corporate or partnership name by authorized officer. Signature [PLEASE SIGN WITHIN BOX] Date Signature (Joint Owners) Date



 

Important Notice Regarding the Availability of Proxy Materials for the Annual Meeting: The Notice, Proxy Statement and Annual Report on Form 10-K are available at www.proxyvote.com. D14048-P36525D43111-P53341 IRONWOOD PHARMACEUTICALS, INC. Annual Meeting of Stockholders Wednesday, June 3, 20202, 2021 9:00 AM Eastern Time This proxy is solicited by the Board of Directors The stockholder(s) hereby appoint(s) Mark MallonThomas McCourt and Gina Consylman, or either of them, as proxies, each with the power to appoint his or her substitute, and hereby authorize(s) them to represent and to vote, as designated on the reverse side of this ballot, all of the shares of common stock of IRONWOOD PHARMACEUTICALS, INC. that the stockholder(s) is/are entitled to vote at the Annual Meeting of Stockholders to be held at 9:00 AM, Eastern Time on Wednesday, June 3, 20202, 2021 via live webcast at www.virtualshareholdermeeting.com/IRWD2020,IRWD2021, and any adjournment or postponement thereof. The stockholder(s) hereby revoke(s) any proxy previously given and acknowledge(s) receipt of the notice and proxy statement for the Annual Meeting of Stockholders. This proxy, when properly executed, will be voted in the manner directed herein. If no such direction is made, this proxy will be voted in accordance with the recommendations of the Board of Directors. Continued and to be signed on reverse side



 

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