QUESTIONS AND ANSWERS

What matters am I voting on? How does the Board recommend that I vote on these matters?

Proposal 1: Election of Directors

The Board is asking stockholders to elect nine directors to the Board, which constitutes the entire Board. Each of the director nominees is standing for election for a one-year term ending at the 2024 annual meeting of stockholders (the “2024 Annual Meeting”) and until his or her successor has been duly elected and qualified, or until such director’s death, resignation or removal.

Proposal 2: Ratification of the Appointment of our Independent Registered Public Accountants for 2023

Stockholders are being asked to ratify the selection of PricewaterhouseCoopers LLP (“PwC”) as our independent registered public accounting firm for the fiscal year ending December 31, 2023.

The Board unanimously recommends that stockholders vote FOR the ratification of PricewaterhouseCoopers LLP as our independent registered public accountants for 2023.

Proposal 3: Non-binding Advisory Vote to Approve Executive Compensation

The Board is asking stockholders to approve, on a non-binding advisory basis, the compensation of the named executive officers as disclosed in this Proxy Statement. The Board has determined to hold this advisory vote on an annual basis. The next advisory vote is expected to take place at the 2024 Annual Meeting. The Board will review the results and take them into consideration when making future decisions regarding executive compensation.

The Board unanimously recommends that stockholders vote FOR the approval of executive compensation on an advisory basis.

Proposal 4: Non-binding Advisory Vote on the Frequency of Future Advisory Votes to Approve Executive Compensation

The Board is asking stockholders to approve, on an advisory basis, that the advisory vote to approve executive compensation occurs every year.

The Board unanimously recommends that stockholders vote 1 YEAR to conduct future advisory votes to approve executive compensation every year.

How do I vote?

If you are a registered stockholder (that is, you hold shares in your name directly on the books of our transfer agent, Broadridge Corporate Issuer Solutions (“Broadridge”), and not through a bank, broker or other nominee) you may choose one of three methods to submit your proxy to have your shares voted in advance of the Annual Meeting:

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QUESTIONS AND ANSWERS

If you are the beneficial owner of shares (that is, you held your shares in “street name” through an intermediary such as a broker, bank or other nominee) as of the Record Date, you will receive instructions from your broker, bank or other nominee as to how to vote your shares or submit a proxy to have your shares voted. PLEASE USE THE VOTING FORMS AND INSTRUCTIONS PROVIDED BY YOUR BROKER, BANK OR OTHER NOMINEE. In most cases, you will be able to do this by mail, via the Internet or by telephone. As discussed herein, your broker, bank or other nominee may not be able to vote your shares on any matters at the Annual Meeting unless you provide instructions on how to vote your shares. You should instruct your broker, bank or other nominee how to vote your shares by following the directions provided by your broker, bank or other nominee.

PLEASE NOTE THAT THIS YEAR, YOUR PROXY CARD LOOKS DIFFERENT. IT HAS MORE NAMES ON IT THAN THERE ARE SEATS UP FOR ELECTION, UNDER NEW REGULATIONS REQUIRING A “UNIVERSAL PROXY CARD” WHICH ARE DESCRIBED IN MORE DETAIL BELOW. THIS MEANS THE COMPANY’S PROXY CARD IS REQUIRED TO LIST HESTIA NOMINEES IN ADDITION TO THE COMPANY’S NOMINEES. PLEASE MARK YOUR CARD CAREFULLY AND ONLY VOTE “FOR” THE NOMINEES AND PROPOSALS AS RECOMMENDED BY YOUR BOARD: THE COMPANY’S EIGHT NOMINEES AND THE ONE RECOMMENDED HESTIA NOMINEE, KATIE MAY. WE ENCOURAGE YOU TO VOTE BY INTERNET OR TELEPHONE TO AVOID POTENTIAL CONFUSION WITH THE UNIVERSAL PROXY CARD. YOU SHOULD ONLY VOTE FOR NINE NOMINEES TOTAL.

Alternatively, you may vote at the virtual Annual Meeting. The Annual Meeting will be held online via a live webcast at [●]. You may only participate in the virtual meeting by registering in advance at [●] prior to the deadline of [●] Eastern Time on [●], 2023. Please have your voting instruction form, proxy card or other communication containing your control number available and follow the instructions to complete your registration request. If you are a beneficial holder, you must obtain a “legal proxy” from your broker, bank or other nominee to participate in the Annual Meeting. Upon completing registration, participants will receive further instructions via email, including unique links that will allow them to access the meeting.

Even if you plan to attend the virtual Annual Meeting, we encourage you to vote your shares on the GOLD proxy card TODAY by Internet, telephone or mail to ensure that your votes are counted at the Annual Meeting.

What is a proxy? What shares are included on a proxy card?

A proxy is your legal designation of another person to vote the stock you own. That other person is called a proxy. If you designate someone as your proxy in a written document, that document is also called a proxy or a proxy card. Our Board has designated [●] and [●] as the Company’s proxies for the Annual Meeting.

Each proxy or voting instruction card represents the shares registered to you as of the close of business on the Record Date. You may receive more than one proxy or voting instruction card if you hold your shares in multiple accounts, some of your shares are registered directly in your name with the Company’s transfer agent, or some of your shares are held in street name through a broker, bank or other nominee. Please vote the shares on each GOLD proxy card or voting instruction card to ensure that all of your shares are counted at the Annual Meeting.

Can I change my vote or revoke my proxy?

Yes. If your shares are registered directly in your name, you may change your vote or revoke your proxy by:

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QUESTIONS AND ANSWERS

If your shares are held in street name, you should contact your broker, bank or other nominee to change your vote or revoke your proxy.

If you have previously submitted a white proxy card sent to you by Hestia, you may change your vote by completing, signing, dating and returning the enclosed GOLD proxy card in the postage-paid envelope provided, or by voting via the Internet or by telephone by following the instructions on the GOLD proxy card. Please note that submitting a white proxy card sent to you by Hestia will revoke votes you have previously made via the Company’s GOLD proxy card.

What is the deadline for voting?

The deadline for voting by telephone or the Internet is [●] p.m. Eastern Time on [●], 2023. Votes cast by mail must be received no later than the start of the Annual Meeting. If you attend the virtual Annual Meeting, you may vote your shares electronically during the meeting.

Who is entitled to vote? How many shares are outstanding? How many votes do I have?

You are entitled to vote at the Annual Meeting if you owned shares of our Common Stock as of the close of business on the Record Date. On the Record Date, [●] shares of our Common Stock were outstanding and eligible to be voted. Each share of Common Stock owned as of the close of business on the Record Date is entitled to one vote on each matter that is properly brought before the Annual Meeting and on which our common stockholders are entitled to vote. Cumulative voting is not permitted in the election of directors.

What vote is required, and how will my votes be counted, to elect the director nominees and to approve each of the other proposals?

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QUESTIONS AND ANSWERS

OUR BOARD UNANIMOUSLY RECOMMENDS VOTING “FOR” THE ELECTION OF EACH OF OUR BOARD’S RECOMMENDED NOMINEES (THE EIGHT COMPANY NOMINEES AND THE ONE RECOMMENDED HESTIA NOMINEE, KATIE MAY) ON PROPOSAL 1, “FOR” PROPOSALS 2 AND 3 AND “1 YEAR” UNDER PROPOSAL 4 USING THE ENCLOSED GOLD PROXY CARD.

How will shares be voted on the universal GOLD proxy card?

The shares represented by any GOLD proxy card that is properly completed, executed and received by the Company prior to or at the Annual Meeting will be voted in accordance with the specifications made on the card, whether it is returned by mail, telephone or Internet.

If you return a validly executed and dated GOLD proxy card without indicating how your shares should be voted on a matter and you do not revoke your proxy, your proxy will be voted: “FOR” the election of all nine director nominees recommended by our Board (including all eight Company Nominees and the one Recommended Hestia Nominee, Katie May) as set forth on the GOLD proxy card (Proposal 1); “FOR” the ratification of the appointment of PwC as our independent registered public accounting firm for fiscal 2023 (Proposal 2); “FOR” the approval, on an advisory basis, of the compensation paid to our named executive officers, as disclosed in thisMay 6, 2024. This Proxy Statement (commonly known as a “say-on-pay resolution”) (Proposal 3); and “1 YEAR” for the approval, on an advisory basis, that the advisory vote to approve executive compensation occurs every year (Proposal 4).

Our Board is not aware of any matters that are expected to come before the Annual Meeting other than those described in this Proxy Statement. If any other matter is presented at the Annual Meeting upon which a vote may be properly taken, shares represented by all GOLD proxy cards received by the Company will be voted with respect thereto at the discretion of the persons named as proxies on the enclosed GOLD proxy card.

Will my shares be voted if I do nothing? What is a broker non-vote?

If you are a registered shareholder of record (i.e., you own your shares directly on the books of our transfer agent and not through a broker) and you do not cast your vote, no votes will be cast on your behalf on any ofcontains information about the items of business at the Annual Meeting.

If your shares are held in “street name” (that is, held for your account by a broker, bank or other nominee), you will receive voting instructions from your broker, bank or other nominee. If you are a street name holder and your shares are registered in the name of a broker, the New York Stock Exchange rules applicable to brokers determine whether your broker may vote your shares in its discretion even if it does not receive voting instructions from you. If you are a street name holder and a broker provides you with competing proxy materials from Hestia (in addition to

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QUESTIONS AND ANSWERS

What if I receive more than one universal GOLD proxy card or set of proxy materials from the Company?

If your shares are held in more than one account, you will receive more than one universal GOLD proxy card, and in that case, you can and are urged to vote all of your shares by completing, signing, dating and returning all universal GOLD proxy cards you receive from the Company in the postage-paid envelope provided. If you choose to vote by telephone or via the Internet, please vote using each universal GOLD proxy card you receive to ensure that all of your shares are voted. Only your latest dated proxy for each account will count. Please sign each proxy card exactly as your name or names appear on the proxy card. For joint accounts, each owner should sign the proxy card. When signing as an executor, administrator, attorney, trustee, guardian or other representative, please print your full name and title on the proxy card.

If Hestia proceeds with its previously announced proxy solicitation, the Company will likely conduct multiple mailings prior to the Annual Meeting to ensure stockholders have the Company’s latest proxy materials to vote. The Company will send you a new universal GOLD proxy card with each mailing, regardless of whether you have previously voted. We encourage you to vote every GOLD proxy card you receive. The latest dated proxy you submit will be counted, and, if you wish to vote as recommended by our Board, then you should only submit GOLD proxy cards.

What should I do if I receive a white proxy card from Hestia?

You may receive proxy solicitation materials from Hestia.

Our Board strongly urges you NOT to sign or return any whiteproxy card sent to you by Hestia. While you may vote for the Company’s Nominees on either the Company’s proxy card or Hestia’s proxy card, we still strongly encourage you to use the universal GOLD proxy card to vote your shares, regardless of how you intend to vote.

If you have previously submitted a proxy card sent to you by Hestia, you can revoke it and vote “FOR” the director nominees recommended by our Board by completing, signing, dating and returning the enclosed GOLD proxy card in the postage-paid envelope provided, or by following the instructions on the GOLD proxy card to vote via the Internet or by telephone. Only the latest validly executed proxy that you submit will be counted, and any proxy may be revoked at any time prior to its exercise at the Annual Meeting as described above. If you attend and validly vote at the Annual Meeting, your proxy will not be used.

Our Board unanimously recommends using the enclosed universal GOLD proxy card to vote “FOR” each of our Board’s recommended nominees (including all eight Company Nominees and the one Recommended Hestia Nominee). Our Board recommends that you DISREGARD any white proxy cards that you may receive.

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QUESTIONS AND ANSWERS

How do I participate in the Annual Meeting?

The Annual Meeting will be held online via a live webcast at [●].You may only participate in the virtual meeting by registering in advance at [●] prior to the deadline of [●] Eastern Time on [●], 2023. Please have your voting instruction form, proxy card or other communication containing your 16-digit control number available and follow the instructions to complete your registration request. If you are a beneficial holder, you must obtain a “legal proxy” from your broker, bank or other nominee to

QUESTIONS AND ANSWERS

Business may not be conducted at the Annual Meeting unless a quorum is present. Under our Amended & Restated By-laws (our “By-laws”),representing a majority of the outstanding voting power of the shares of our Common Stock, present or represented by proxy, andvotes entitled to votebe cast at the Annual Meeting constitutes a quorum. WhereIf you submit your proxy by Internet, telephone or proxy card, you will be considered part of the quorum. Abstentions and broker non-votes are included in the count to determine a separatequorum.

QUESTIONS AND ANSWERS

Do I have any dissenters’ or appraisal rights with respect to any of the matters to be voted on at the Annual Meeting?

No. Delaware law does not provide stockholders any dissenters’ or appraisal rights with respect to the matters to be voted on at the Annual Meeting.

How do I request a paper copy of the proxy materials?

A copy of our proxy materials, as filed with the SEC, is available, without charge, by mailing a request to Investor Relations, investorrelations@pb.com. The proxy materials are posted on our website at www.investorrelations.pitneybowes.com and are available from the SEC at its website, www.sec.gov.

Whom do I contact if I have questions about the Annual Meeting?

If you have any questions or need any assistance in voting your shares, please contact our proxy solicitor:

Morrow Sodali LLC

509 Madison Avenue, Suite 1206

New York, NY 10022

Banks and Brokers Call: (203) 561-6945

Stockholders Call Toll Free: (800) 662-5200

E-mail:PBI@investor.morrowsodali.com

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BACKGROUND TO THE SOLICITATION

Background to the Solicitation

The summary below details significant contacts between the Company and Hestia beginning in November 2021 through the date of this Proxy Statement. During this period, the Company, under the leadership ofBy-laws amendments the Board and management, has:

On November 20, 2021, representatives of Hestia contacted the Pitney Bowes investor relations team to set up a conference call to discuss the Company and the recent quarterly results.

On November 23, 2021, Ned Zachar, Vice President of Investor Relations at Pitney Bowes, and Alex Brown, Senior Manager of Investor Relations at Pitney Bowes, held an introductory call, scheduled at Hestia’s request, with Kurt Wolf, Chief Investment Officer of Hestia, and Lee Miles, a senior analyst at Hestia, during which Mr. Zachar and Mr. Brown provided an overview of Pitney Bowes’ businesses.

Following that conversation, over the course of the next several months, Mr. Zachar and Mr. Brown held a number of virtual meetings and engaged in email correspondence with Hestia’s representatives. During this period, the Company gave Hestia the opportunity to provide its input on the Company and to ask questions of Company management, and the Company provided information requested by Hestia, including regarding the Company’s business units and performance.

On March 16, 2022, Marc Lautenbach, President and CEO of Pitney Bowes, Ana Chadwick, the Chief Financial Officer of Pitney Bowes, Mr. Zachar and Mr. Brown held a virtual meeting with Hestia’s representatives, during which Hestia’s representatives discussed its sum-of-the-parts valuation of the Company and the Global Ecommerce business.

Following that conversation, over the course of the next several months, members of Pitney Bowes’ investor relations team continued to hold virtual meetings with Hestia’s representatives concerning Pitney Bowes’ businesses and financial results.

On May 25, 2022, Mr. Miles, on behalf of Hestia, and representatives of certain other Company stockholders attended a tour of Pitney Bowes’ Atlanta facility, which was also attended by several representatives of Pitney Bowes, including Ms. Chadwick, Mr. Zachar, Mr. Brown, business representatives from the Company’s Global Ecommerce and Presort Services units, and external buy- and sell-side analysts.

On June 28, 2022, in a virtual meeting between Ms. Chadwick, the Company’s investor relations team and Hestia’s representatives, the representatives of Hestia shared their views regarding the fair market value of Pitney Bowes stock and confirmed their intent to send a letter to the Board outlining Hestia’s perspective on the Company’s value.

On July 1, 2022, in a subsequent virtual meeting between Mr. Wolf, on behalf of Hestia, and the Company’s investor relations team, Mr. Wolf outlined his thesis for value creation at Pitney Bowes and reiterated his intent to document this thesis in a letter to the Board.

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BACKGROUND TO THE SOLICITATION

On July 6, 2022, Hestia sent a non-public letter to the Board which summarized its thesis for value enhancement at Pitney Bowes. The thesis centered on (i) the spin-off or sale of Global Ecommerce or certain business units within Global Ecommerce, (ii) authorizing a share repurchase program and (iii) the sale of the Pitney Bowes Bank.

On July 12, 2022, Company management, including Mr. Lautenbach, Ms. Chadwick and Dan Goldstein, the Chief Legal Officer and Corporate Secretary of Pitney Bowes, held a virtual meeting with Mr. Wolf to discuss the contents of Hestia’s July 6 letter, during which Company management requested the assumptions underlying Hestia’s valuation of the Company and its business units. Mr. Wolf declined to provide this information.

Following that conversation and over the course of the next several months, representatives from the Company, including Mr. Lautenbach, Mr. Zachar and Mr. Brown, continued to actively engage with representatives of Hestia, including Mr. Wolf and Mr. Miles, and discuss a range of topics related to the Company, including Hestia’s views on the Company and its performance and strategy, and Hestia’s intentions. This included hosting a tour of the Company’s Global Ecommerce facility in Los Angeles and dinners on September 27 and 28, 2022, which were attended by Mr. Wolf, on behalf of Hestia, along with several of the Company’s other debt and equity holders, and during which Pitney Bowes’ business and capital allocation strategy were discussed.

On October 11, 2022, Hestia sent another non-public letter to the Board stating that Hestia appreciated management’s engagement, and elaborating on certain concerns and suggesting that the Board publicly commit to exploring a divestiture of its Global Ecommerce businesses.

On November 1, 2022, Mr. Wolfemailed Mr. Lautenbach stating that Hestia was nearly a 5% stockholder and requesting a meeting with members of the Board.

On November 11, 2022, Mr. Lautenbach held a call with Mr. Wolf to further discussHestia’s November 10 presentation.

After the call, Mr. Wolf sent to certain members of Company management and the Board, including Mr. Lautenbach, Mr. Roth, Ms. Busquet and Ms. Sanford a copy of the November 10 presentation and a draft term sheet outlining the key terms of Hestia’s proposed settlement. Such terms included, among others, (i) the appointment of three unnamed directors to the Board, (ii) the resignation of two directors from the Board and (iii) the formation of a four-person ‘Strategic Review Committee’ to be composed of two of Hestia’s nominees, one of which would serve as chair, and two existing directors.

On November 14, 2022, Mr. Roth, on behalf of the Board, sent an email to Mr. Wolf indicating that the Board was always open to evaluating opportunities for Board refreshment and planned to carefully evaluate Hestia’s proposal and requesting the names of Hestia’s three director candidates. Mr. Wolf responded on November 15, 2022 and indicated that two of Hestia’s proposed nominees would be Katie May and another individual, who was not ultimately included in Hestia’s slate (the “Withdrawn Hestia Candidate”).

On November 16, 2022, Mr. Roth, on behalf of the Board, wrote to Mr. Wolf to confirm that Ms. May and the Withdrawn Hestia Candidate were viable director candidates and informed him that the Board was prepared to begin the interview process for each of them as soon as Hestia provided their contact information. Mr. Roth also reiterated the Board’s intent to expeditiously reach a conclusion regarding Hestia’s proposal.

Later that morning, Mr. Wolf sent another draft of the term sheet to Mr. Roth (the “November 16 Term Sheet”). The November 16 Term Sheet was substantially similar to the term sheet sent on November 11; it reiterated that Ms. May and the Withdrawn Hestia Candidate were two of Hestia’s nominees and named Mr. Wolf as Hestia’s third nominee.

22

BACKGROUND TO THE SOLICITATION

On November 17, 2022, after reviewing the term sheet, Mr. Roth confirmed with Mr. Wolf that Pitney Bowes would invite all of Hestia’s proposed director candidates to interview as soon as practicable, with a view to determining the suitability of the proposed nominees, and reiterated the Company’s position that the Board should first evaluate Hestia’s proposed director candidates before formally responding to Hestia’s proposal.

On November 17, 2022,a representative of Olshan Frome Wolosky LLP, counsel to Hestia (“Olshan”), proposed Ken McBride as an additional director candidate for Pitney Bowes’ consideration.

On November 21, 2022, Hestia filed a Schedule 13D with the SEC disclosing that it had acquired a 6.9% stake in the Company.

On December 5, 2022, following its review and evaluation of the November 16 Term Sheet, the Board approved a counterproposal which included (i) expanding the size of the Board to 11 directors, (ii) adding Ms. May and the Withdrawn Hestia Candidate to the Board as independent directors, and (iii) amending the charter of the existing Finance Committee, which already charged the Finance Committee to consider and advise the Board on matters related to capital allocation and major corporate transactions, to – in line with the strategy committee proposed by Hestia – explicitly incorporate into the Finance Committee’s charter the Committee’s consideration of the intersection between the Company’s strategy and the implications of that for capital allocation and corporate transaction decision.

Later on December 5, 2022, a representative of Cravath, Swaine and Moore LLP, counsel to Pitney Bowes (“Cravath”), sent a revised term sheet to a representative of Olshan, with the Board-approved counterproposal. On a call with a representative of Cravath later that day, a representative of Olshan rejected the counterproposal, indicating that Hestia would only accept a settlement which included three of Hestia’s director candidates being appointed to the Board. Later that day, a representative of Olshan emailed a revised term sheet to Cravath, which was substantially similar to the November 16 Term Sheet, save that it accepted the Company’s proposal to amend the charter of the existing Finance Committee rather than create a new committee, as originally proposed by Hestia. The next day, Olshan reiterated this position to a representative of Cravath and a representative of J.P. Morgan Securities LLC (“J.P. Morgan”), financial advisor to Pitney Bowes.

On December 7, 2022, a representative of Cravath sent an email to a representative of Olshan confirming that the Board was not prepared to add Mr. Wolf to the Board, as the Board had concluded that he lacked the skill set, experience and track record necessary to positively impact the Company’s operations and create value for its stockholders, but was prepared to appoint Ms. May and the Withdrawn Hestia Candidate to the Board. The representative of Olshan indicated that Mr. McBride would be an acceptable alternative to Mr. Wolf as the third director candidate.

Later that day, a representative of Olshan confirmed that Hestia’s “best and final” offer would be a Board including Ms. May, the Withdrawn Hestia Candidate, and one of either Mr. Wolf or Mr. McBride.

Following these meetings, members of the Board determined that it was in the best interests of the Company to reject Hestia’s offer, primarily because the Board deemed Mr. Wolf and Mr. McBride to be unsuitable director candidates.

On December 9, 2022, representatives ofCravath and J.P. Morgan had a call with a representative of Olshan where they noted the Board’s concerns with Mr. Wolf and Mr. McBride as candidates and reiterated that Pitney Bowes remained open to a settlement with two directors proposed by Hestia.

On December 12, 2022, Hestia issued an open letter to the Company’s stockholders, in which it criticized the Company’s engagement with Hestia and its proposed director candidates and announced plans to nominate a majority slate of director candidates to the Board, including a proposed interim CEO. Also on the same day, Hestia filed an amended Schedule 13D with the SEC, disclosing a 7.2% stake in Pitney Bowes.

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BACKGROUND TO THE SOLICITATION

On December 13, 2022, a representative of Olshan requested a copy of the representation agreement required by Pitney Bowes’ By-laws to be signed by any director candidate nominated by a stockholder, which was provided by a representative of Sidley Austin LLP, counsel to Pitney Bowes (“Sidley”).

On January 11, 2023, a representative of Sidley met with a representative from Olshan and explored potential settlement terms. During this meeting, the Olshan representative indicated that Hestia might be willing to settle for three mutually acceptable independent directors – excluding Mr. Wolf or any other person affiliated with Hestia.

On January 16, 2023, a representative of Sidley had a call with a representative from Olshan to follow up on their previous meeting. Among other things, the Olshan representative confirmed that the three mutually acceptable directors would not include Mr. Wolf or any other person affiliated with Hestia. The Olshan representative also confirmed that at least one incumbent director would have to depart the Board. He said that Hestia would not object to Mr. Lautenbach remaining CEO. In terms of director candidates, the Sidley representative indicated that Ms. May and the Withdrawn Hestia Candidate would continue to be acceptable to the Board, but that the Board would object to Mr. McBride because his appointment could be damaging for the Company. Later that day, the Olshan representative emailed the Sidley representative, explaining that the Withdrawn Hestia Candidate would not be available for a settlement unless the majority of the Board turns over.

On January 18 and 19, 2023, the representative of Sidley and the representative from Olshan had an email exchange, during which the Sidley representative promised to revert with feedback from the Board to Hestia’s proposal early or mid-week of the Week of January 23.

On January 23, 2023, Hestia delivered a nomination notice to Mr. Goldstein, informing Pitney Bowes of Hestia’s nomination of a majority slate of seven director candidates to the Board: Milena Alberti-Perez, Todd A. Everett, Carl J. Grassi, Ms. May, Mr. McBride, Lance E. Rosenzweig and Mr. Wolf (the “Hestia Nominees”). This was the first time that Hestia had made the names of Ms. Alberti-Perez, Mr. Everett, Mr. Grassi, and Mr. Rosenzweig known to Pitney Bowes. Later that morning, Hestia issued a press release announcing its nominations. Hestia also released a presentation outlining the background to its campaign and providing additional details on Hestia’s nominees.

Later that day, Pitney Bowes issued a press release stating, among other things, that, consistent with its fiduciary duties to stockholders and the Company’s governing documents, the Board would review Hestia’s nominations and highlighted the Company’s continuing interest in considering well-qualified candidates to join the Board and the Company’s offer to appoint two candidates proposed by Hestia to the Board in December.

Also on January 23, 2023, Hestia delivered a letter to the Board requesting that the Board take action such that the election of the Hestia Nominees would not be a considered a change in control under certain of the Company’s material contracts and agreements.

Later that day, the Sidley representative called the Olshan representative to deliver a counterproposal on behalf of the Board, pursuant to which the Board would agree to (i) appoint Ms. May plus two other mutually agreed-upon independent directors to the Board and (ii) one director would depart the Board. In exchange, the Board expected a standstill lasting through the 2024 annual meeting. Later that day, after consulting with Hestia, the Olshan representative reverted via email and indicated that Hestia would require no less than three of its nominees to be appointed to the Board and at least two incumbent directors to depart. He also stated that a two-year standstill would be out of question.

On January 24, 2023, Hestia delivered a books and records demand for stockholder list materials to the Company.

Also on January 24, 2023, Hestia filed an amended Schedule 13D with the SEC that included the details of Hestia’s Board nominations.

On January 31, 2023, Sidley sent a letter to Olshan in response to Hestia’s books and records demand, and subsequently provided the requested materials. On the same day, Sidley sent a letter to Olshan in response to Hestia’s letter regarding the change in control provisions under the Company’s material contracts, stating that the Board would consider approving the Hestia Nominees for the sole purpose of these change in control provisions.

24

BACKGROUND TO THE SOLICITATION

On February 9, 2023, a representative of Sidley held a call with a representative of Wilson Sonsini Goodrich & Rosati, counsel to Hestia (“Wilson Sonsini”), to discuss potential settlement terms. As authorized by the Board, the representative of Sidley offered a settlement that included (i) the appointment of three new directors to the Board: Ms. May and Mr. Everett (provided that his competition issues could be resolved) as well as one mutually agreed independent director; (ii) the resignation of two of Pitney Bowes’ existing directors; and (iii) a one-year standstill, to be extended in the event the Hestia nominees would be renominated for the 2024 annual meeting. The representative of Wilson Sonsini conveyed that Hestia, despite never having raised the point in previous discussions, would only accept a settlement that involved the resignation of both CEO Mr. Lautenbach and Chairman Mr. Roth.

On the same day, Sidley sent a letter to Olshan confirming that the Board had approved the Hestia Nominees for the sole purpose of the change in control provisions in certain of the Company’s debt instruments.

On February 14, 2023, Mr. Wolf emailed members of the Board, including Mr. Roth, Ms. Busquet and Ms. Sanford, with yet another “final offer,” which included the following: (i) three directors designated by Hestia would be immediately added to the Board (provided that Mr. Wolf would not be one of the directors added, if that be the Board’s preference); (ii) the Board would implement a mandatory retirement age for directors of 75 years of age, effective as of the 2024 Annual Meeting; (iii) Mr. Lautenbach would not be nominated at the Annual Meeting; (iv) no directors, other than the three Hestia nominees referenced above, would be added to the Board through 2024, unless accompanied by an equal number of retirements of currently serving directors, notwithstanding the demanded retirement of Mr. Lautenbach; (v) the Board would commit to replacing the CEO; (vi) the Board would immediately form a committee focused solely on CEO succession planning that would (a) include four independent directors with less than a decade of service, including two Hestia designees and two incumbent directors, (b) be co-chaired by a Hestia designee and an incumbent director, (c) be empowered to retain independent advisors to run a CEO search, and (d) act in an advisory role, while the Board would retain authority to select the next CEO; and (vii) that Hestia would agree to customary settlement terms, including a one-year standstill agreement.

On February 21, 2023, Mr. Roth and Ms. Busquet had a call with Mr. Wolf to discuss Hestia’s recent settlement proposal. As authorized by the Board, Mr. Roth rejected Hestia’s proposal and offered a settlement counterproposal that included: (i) a mandatory director retirement age of 75; (ii) the appointment of three new mutually agreed independent directors to the Board, with Hestia to consider candidates identified by an external search firm engaged by Pitney Bowes; (iii) two of Pitney Bowes’ existing directors would not stand for reelection at the Annual Meeting; and (iv) a one-year standstill, along with other customary terms. Mr. Wolf indicated on the call that this proposal would not be acceptable to Hestia and subsequently confirmed this in a subsequent email on February 22, 2023.

On March 2, 2023, the Company announced (i) the appointments of Steven Brill and Darrell Thomas to the Board, effective immediately, (ii) that Board Chair Michael I. Roth and directors S. Douglas Hutcheson and David L. Shedlarz would not stand for re-election at the Annual Meeting, and (iii) that Bob Dutkowsky would immediately assume the role of Non-Executive Chair of the Board.

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CERTAIN EFFECTS OF HESTIA’S SOLICITATION

Certain Effects of Hestia’s Solicitation

Hestia is seeking to replace seven of the directors on our Board at the Annual Meeting. Certain of our material agreements and other legal instruments could be impacted if a “change in control” is deemed to occur if Hestia’s proxy solicitation is successful. Generally, a change in control would be deemed to occur under these material agreements and other legal instruments if current members of the Board cease to constitute at least a majority of the Board as a result of an actual or threatened proxy contest. Immediatelyadopt following the Annual Meeting, our Board will be composed of nine members, meaning that a change in control could be deemed to occurrequire the information required under these material agreements and other legal instruments if five or more directors are replaced at the Annual Meeting.

The electionRule 14a-19 of the Hestia nominees couldExchange Act).