QUESTIONS AND ANSWERS

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

If your broker does not have discretionary voting authorityshares are held in more than one account, you will receive more than one universal GOLD proxy card, and in that case, you do not provide voting instructions, or ifcan and are urged to vote all of your shares by completing, signing, dating and returning all universal GOLD proxy cards you abstain on one or more agenda items,receive from the effect would be as follows:

QUESTIONS AND ANSWERS

What happens if Hestia withdraws or abandons its solicitation or fails to comply with the new rules and I already granted proxy authority in favor of Hestia?

Stockholders are encouraged to submit their votes on the board of directorsuniversal GOLD proxy card. If Hestia withdraws or abandons its solicitation or fails to comply with the company. The board of directors will reviewuniversal proxy rules after a stockholder has already granted proxy authority, stockholders can still sign and date a later submitted universal GOLD proxy card. If Hestia withdraws or abandons its solicitation or fails to comply with the results and take them into consideration when making future decisions regarding executive compensation. Broker non-votes and abstentions are not considereduniversal proxy rules any votes cast in favor of Hestia’s nominees will be disregarded and thereforenot be counted, whether such vote is provided on the Company’s universal GOLD proxy card or on Hestia’s white proxy card.

What is a universal proxy? Will it be used in connection with the Annual Meeting?

The SEC recently adopted Rule 14a-19 under the Securities Exchange Act of 1934, as amended (the “Exchange Act”), commonly referred to as the “universal proxy rules,” requiring the use of a universal proxy card in contested director elections that take place after August 31, 2022. This means that all of the Company’s nominees and any dissident nominees will be listed on each proxy card that is sent to stockholders in connection with a contested meeting. Stockholders may vote for nominees from either or both of the Company’s slate and the dissident slate, but in any event may not vote for more nominees than there are seats available to be filled. Even though we are required to include the Hestia nominees on our universal GOLD proxy card, it does not mean that we recommend voting for them. Your Board is ONLY recommending that stockholders vote for the eight Company Nominees and the one Recommended Hestia Nominee, Katie May.

Because Hestia Capital Partners, LP (together with its affiliates, “Hestia”) has provided notice of its intent to nominate candidates for election to the Board at the Annual Meeting, this year’s director elections are considered contested, and a universal proxy card will be used. 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.

What happens if I return a universal proxy card but give voting instructions for more than nine candidates?

An “over-vote” occurs when a stockholder submits more votes “FOR” director nominees than there are Board seats up for election. To the extent an over-vote (e.g., voting “FOR” with respect to more than nine nominees on Proposal 1) occurs on a record holder’s universal proxy card and it is not corrected, all of such record holder’s votes on Item 1 regarding nominees will be invalid and will not be counted. In addition, depending on the broker, bank, or other nominee through which you hold your shares, your votes on all other proposals before the Annual Meeting may also be invalid and not counted. We encourage you to vote by Internet or telephone to avoid an “over-vote.”

What happens if I return a universal proxy card but give voting instructions for fewer than nine candidates?

An “under-vote” occurs when a stockholder submits fewer votes “FOR” director nominees than there are director seats up for election. To the extent an under-vote (i.e., voting “FOR” with respect to fewer than nine nominees on Proposal 1) occurs on any stockholder’s universal proxy card, your shares will only be voted FOR those nominees you have so marked and “WITHHOLD” for the other nominees. We encourage you to vote by Internet or telephone to avoid an “under-vote.”

Who may attend the Annual Meeting?

The Annual Meeting will be held in a virtual-only format. You are entitled to participate in the Annual Meeting only if you were a holder of Common Stock as of the close of business on the Record Date, or your authorized representative or you hold a valid proxy for the Annual Meeting. Stockholders must pre-register in order to attend and vote by ballot at the Annual Meeting. Please see the section below “How do I participate in the Annual Meeting?” for instructions about how to pre-register.Even if you plan to attend the virtual Annual Meeting, we recommend that you also vote by proxy as soon as possible so that your vote will be counted either forif you later are unable or against. Asdecide not to attend the virtual Annual Meeting.

17

QUESTIONS AND ANSWERS

How do I participate in the Annual Meeting?

The Annual Meeting will be held online via a result,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, non-votes and abstentionsbank 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.

Stockholders may log into the meeting platform beginning at [●] Eastern Time on [●], 2023. We encourage you to log in prior to the meeting start time. We will have no effecta support team ready to assist attendees with any technical difficulties they may have accessing or hearing the audio webcast of the meeting.

Additional information and our proxy materials can also be found at [●]. If you have any difficulty following the registration process, please email [●] or call [●].

May I submit questions during the Annual Meeting?

Yes. We expect that members of the Board and management, as well as representatives of our independent registered public accounting firm, PwC, will attend the virtual Annual Meeting and be available to answer stockholder questions. We will provide our stockholders the opportunity to ask questions. Questions submitted during the meeting pertinent to meeting matters will be answered during the meeting, subject to time constraints. Instructions for submitting questions and making statements will be posted on the advisoryvirtual meeting website. This question and answer session will be conducted in accordance with certain Rules of Conduct. These Rules of Conduct will be posted on our investor relations website prior to the date of the Annual Meeting, and may include certain procedural requirements.

Why are you conducting a virtual-only Annual Meeting?

We are conducting the Annual Meeting in a virtual format, similar to the past several years, because it provides our stockholders with expanded access to the Annual Meeting regardless of physical location, and allows stockholders who would not otherwise be able to attend the Annual Meeting the opportunity to do so. Like our prior in-person and virtual annual meetings, we will provide our stockholders with ample opportunity to ask questions at the Annual Meeting.

What if I experience technical issues with the virtual meeting platform?

We will have technicians ready to assist you with any technical difficulties you may have accessing the virtual meeting. If you encounter any difficulties accessing the virtual meeting during check-in or during the Annual Meeting, please call the technical support number that will be posted on the virtual meeting platform log-in page. We encourage you to access the virtual meeting prior to the start time.

If I can’t attend the Annual Meeting, can I vote later?

We encourage stockholders to approve executive compensation.vote and submit their proxy in advance of the Annual Meeting by one of the methods described in the proxy materials, regardless of whether you think you will be able to attend the Annual Meeting. Any votes submitted after the closing of the polls at the Annual Meeting will not be counted.

What constitutes a quorum?

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.

18

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”), a majority of the outstanding voting power of the shares of our Common Stock, present or represented by proxy, and entitled to vote at the Annual Meeting, constitutes a quorum. Where a separate vote by a class or series is required, the holders of a majority in voting power of all issued and outstanding stock of such class or series entitled to vote on such matter, present in person or represented by proxy, shall constitute a quorum entitled to take action with respect to such matter. If there are not sufficient shares present or represented by proxy at the Annual Meeting to constitute a quorum for approval of any matter to be voted upon, the Annual Meeting may be adjourned to permit further solicitation of proxies in order to achieve a quorum. Abstentions or withheld votes and broker non-votes are counted as shares present and entitled to vote for purpose of determining whether a quorum is present.

What happens if the Annual Meeting is adjourned?

Unless a new record date is fixed, your proxy will still be valid and may be used to vote shares of our Common Stock at the adjourned Annual Meeting. You will still be able to change or revoke your proxy until it is used to vote your shares.

Who will count the votes?

A representative of [●] will count the votes and serve as the independent inspector of election at the Annual Meeting.

Where can I find the results of the Annual Meeting?

We will report the voting results of the Annual Meeting in a Current Report on Form 8-K filed with the SEC within four business days following our Annual Meeting, a copy of which will also be available on our website, https://www.investorrelations.pitneybowes.com/.

How do Dividend Reinvestment Plan participants or employees with shares in the 401(k) plans vote by proxy?

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

20

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 option.Proxy Statement. During this period, the Company, under the leadership of 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.

21

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.

23

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.

25

CERTAIN EFFECTS OF HESTIA’S SOLICITATION

Certain Effects of Hestia’s Solicitation

Hestia is seeking to replace seven of the directors on our 2020 annual report mayBoard at the Annual Meeting. Certain of our material agreements and other legal instruments could be viewed onlineimpacted 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

The election of the Hestia nominees could be deemed to constitute a change in control under the caption “Investor Relations”.

CORPORATE GOVERNANCE

Corporate Governance website at

CORPORATE GOVERNANCE

The board,Board, as well as each of its committees, is engaged in an intentional and ongoing process to evaluate both the needs of the Board through looking forward at the skills necessary for the Company as it continues to transform and through reviewing the individual contributions of each Board member and the way that the Board as a whole communicates and works together. As part of this process, the Board circulates to its members on an annual basis a performance assessment questionnaire. The results of the assessment are reviewed by the respective committees, with a view toward taking action to address issues presented. The Governance Committee assesses the contributions of each director annually and determines the skill set required for new members joining the board.

CORPORATE GOVERNANCE

Board Committees and its impact to the company’s employees, clients, operations, and financial performance. In the early days of the crisis, the board focused two of its meetings almost entirely on the risks related to COVID and the strategy both during and after COVID, and dedicated significant time in additional board meetings and in ad hoc updates about COVID. (See page 34 for additional discussion about the company’s response to COVID-19).

CORPORATE GOVERNANCE