SEC Form DEF 14A filed by Tompkins Financial Corporation

The Annual Meeting of Shareholders (the “Annual Meeting”) of Tompkins Financial Corporation (“Tompkins” or the “Company”) will be held on Tuesday, May 13, 2025 at 10:00 a.m. at the Company's headquarters, located at 118 E. Seneca Street, Ithaca, New York, 14850, for the following purposes:

If you wish to attend the Annual Meeting in person, you must register your planned in-person attendance with us at least five (5) business days prior to the meeting by writing to Tracy Kinner, Executive Assistant, Tompkins Financial Corporation, PO Box 460, Ithaca, NY 14851, or by email at [email protected]. Pre-registration and matching picture identification are necessary to gain entrance to the secure area of our headquarters building where the meeting will be held. Parking is generally available on-street, or at the public garages on Seneca Street and Cayuga Street. The parking spaces under the building will be reserved for those requiring accessible parking with a valid plate or placard. The meeting will focus largely on the business items described in the Proxy Statement. A brief question and answer session will be held immediately following the meeting.

We have elected to take advantage of Securities and Exchange Commission (“SEC”) rules that allow us to furnish proxy materials to certain shareholders over the internet. We believe furnishing proxy materials to our shareholders over the internet allows us to provide our shareholders with the information they need, while lowering the costs of delivery and reducing the environmental impact of the Annual Meeting. If you have received the Notice of Internet Availability, you will not receive a printed copy of the proxy materials unless you request it by following the instructions for requesting such proxy materials contained in the Notice of Internet Availability and summarized in the proxy statement.

The Company’s Board of Directors (the “Board”) has fixed the close of business on March 17, 2025 as the record date for determining shareholders entitled to notice of and to vote at the Annual Meeting. Only shareholders of record at the close of business on that date are entitled to vote at the Annual Meeting.

The Board of Directors unanimously recommends that you vote “FOR” each of the director nominees named in the enclosed proxy statement, “FOR” advisory approval of the compensation paid to the Company’s named executive officers, and “FOR” ratification of the appointment of KPMG LLP as the Company’s independent auditor for the fiscal year ending December 31, 2025. Your vote is important regardless of the number of shares you own. It is important that your shares be represented at the Annual Meeting whether or not you are personally able to attend. Accordingly, after reading the accompanying proxy statement, please promptly submit your proxy by telephone, internet or mail as described in the proxy statement. Submitting your proxy by telephone, internet or mail does not deprive you of the right to attend or vote at the Annual Meeting or to vote your shares in the manner described in the accompanying proxy statement.

We are providing this proxy statement (the “Proxy Statement”) in connection with the solicitation of proxies on behalf of the Board of Directors (the “Board”) of Tompkins Financial Corporation (“Tompkins” or the “Company”) for use at the Annual Meeting of Shareholders, to be held on Tuesday, May 13, 2025 at 10:00 a.m. Eastern Daylight Saving Time (the “Annual Meeting”) at the Company's headquarters, 118 E. Seneca Street, Ithaca, New York, 14850. The Annual Meeting will be held in-person. This Proxy Statement summarizes the information that you will need in order to vote. We first made this Proxy Statement and form of proxy available to shareholders on or about April 1, 2025.

In accordance with rules adopted by the SEC, instead of mailing a printed copy of our proxy materials to each shareholder of record, we furnished our proxy materials, including the Notice of Annual Meeting of Shareholders, this Proxy Statement, the corporate report and the annual report on Form 10-K for the fiscal year ended December 31, 2024 (the “Annual Report”), by sending a notice of internet availability of proxy materials (the “Notice of Internet Availability”) and providing access to such documents over the internet. Generally, shareholders will not receive printed copies of the proxy materials unless they request them. Shareholders of record who prefer to receive a paper or e-mail copy of our proxy materials must follow the instructions below or as provided in the Notice of Internet Availability for requesting such materials. The Notice of Internet Availability only identifies the items to be voted on at the Annual Meeting. You cannot vote by marking the Notice of Internet Availability and returning it.

To view ONLINE: visit www.ProxyVote.com 24 hours a day, seven days a week, through the conclusion of the Annual Meeting. You will need your Notice of Internet Availability with your control number in order to log in and view the proxy materials.

To receive a PAPER or E-MAIL copy: you MUST REQUEST a paper or e-mail copy of the proxy materials. There is NO charge to receive a paper or e-mail copy of the materials. Please choose one of the following methods for your request prior to April 24, 2025:

If your shares are held by a stock brokerage account or by a bank or other nominee, you are considered the “beneficial owner” of the shares, and those shares are referred to as being held in “street name.” As the beneficial owner of those shares, you have the right to direct your broker, bank, or nominee how to vote your shares, and you should receive separate instructions from your broker, bank, or other holder of record describing how to vote your shares and access the proxy materials. You also are invited to attend the Annual Meeting. However, because a beneficial owner is not the shareholder of record, you may not vote these shares at the Annual Meeting unless you obtain a “legal proxy” from the broker, bank, or nominee that holds your shares, giving you the right to vote the shares at the Annual Meeting.

Only shareholders of record at the close of business on March 17, 2025 are entitled to receive notice of and to vote at the Annual Meeting. On March 17, 2025, there were 14,434,103 shares of the Company’s common stock, par value $0.10 per share (our “common stock”), outstanding and entitled to vote. Each share of common stock is entitled to one vote on each matter to be voted on at the Annual Meeting. Other than the common stock, there are no voting securities of Tompkins outstanding. There is no cumulative voting with respect to the election of directors.

Shareholders of record may vote their common stock through the following methods:

The deadline for submitting voting instructions via the Internet or by telephone for shares held directly is 11:59 p.m., Eastern Daylight Saving Time, on May 12, 2025. For shares held in the Tompkins Financial Corporation Employee Stock Ownership Plan (the “ESOP”) and the Tompkins Retirement Savings Plan (the “401(k) Plan”), the votes need to be cast by 6:00 a.m., Eastern Daylight Saving Time, on May 9, 2025. The last-dated proxy or voting instructions you submit (by any means) will supersede any previously submitted proxies and voting instructions.

If you are a record shareholder and you attend the Annual Meeting, you may vote by completing a ballot, which will be available at the Annual Meeting. If your shares are held in the ESOP or the 401(k) Plan, you may not vote in person at the Annual Meeting.

All properly signed proxies returned in time to be counted at the Annual Meeting will be voted by the named proxies at the Annual Meeting. Where you have specified how your shares should be voted on a matter, your shares will be voted in accordance with your instructions; if you properly sign your proxy card, but you do not indicate how your shares should be voted on a matter, your shares will be voted as the Board recommends. Executed proxies with no instructions will be voted “FOR” all Director Nominees listed in Proposal 1, and “FOR” Proposals 2 and 3.

If your shares are held in the ESOP and/or the 401(k) Plan, your vote will serve as instructions to the trustee of the ESOP and/or the 401(k) Plan. If you do not vote the shares allocated to your account, your shares will be voted by the trustee in the same proportion as it votes the shares of the plan participants who instruct the trustee on how to vote.

Shareholders of record who submit proxies retain the right to revoke them at any time before they are exercised. Unless revoked, the common stock represented by such proxies will be voted at the Annual Meeting. If you are a shareholder of record, you may revoke your proxy at any time before it is actually exercised at the Annual Meeting by:

The last-dated proxy or voting instructions you submit (by any means) will supersede all previously-submitted proxies and voting instructions. If you hold your common stock in “street name” and instructed your broker, financial institution or other nominee to vote your common stock and you would like to revoke or change your vote, then you must follow the instructions received from your nominee to change your vote.

The presence, in person or by proxy, of the holders of at least a majority of the shares of our common stock entitled to vote at the Annual Meeting is necessary to constitute a quorum for the conduct of business at the Annual Meeting.

The Company’s Board of Directors knows of no other business to be presented for shareholder action at the Company’s Annual Meeting. If any other matters are properly brought before the Annual Meeting, the individuals named on the proxy card will vote your shares in their discretion on such matters.

At the Annual Meeting, abstentions, votes cast in person or by proxy and broker non-votes will each be counted for purposes of determining the presence of a quorum. A “broker non-vote” occurs when a broker, bank, or other nominee holding shares for a beneficial owner does not vote on a particular proposal because the nominee does not have discretionary voting power on that matter and has not received instructions from the beneficial owner. At the Annual Meeting, broker non-votes and abstentions will have no effect on the outcome of any of the Company’s proposals. Brokers, banks or other nominees will not have discretionary authority to vote on Proposal No. 1 or 2, but will have discretionary authority to vote on Proposal No. 3.

The enclosed proxy is being solicited by the Board. The total cost of solicitation of proxies in connection with the Annual Meeting will be borne by the Company. In addition to solicitation by mail, our directors, officers and employees may solicit proxies for the Annual Meeting personally or by telephone or electronic communication without additional remuneration. The Company will also provide brokers and other record owners holding shares in their names or in the names of nominees, in either case which are beneficially owned by others, proxy materials for transmittal to such beneficial owners and will reimburse such record owners for their expenses in doing so.

At the Annual Meeting, eleven (11) directors will be elected for a one-year term expiring at the 2026 Annual Meeting, and with respect to each director, until their successor is elected and qualified. The following director nominees are currently serving as directors: Nancy E. Catarisano; Janet M. Coletti; Daniel J. Fessenden; Patricia A. Johnson; Angela B. Lee; John D. McClurg; Ita M. Rahilly; Stephen S. Romaine; and Michael H. Spain. Their terms expire in 2025, and each is standing for re-election at the Annual Meeting. Each director was identified and nominated by the Nominating & Corporate Governance Committee for election at the Annual Meeting. Heidi M. Davidson and Helen Eaton, currently serving on the Community Bank Boards of Tompkins Community Bank Hudson Valley and Tompkins Community Bank Pennsylvania, respectively, were also identified and nominated by the Nominating & Corporate Governance Committee for election at the Annual Meeting for a term of one year.

The 11 nominees receiving the highest number of affirmative votes of the shares entitled to vote at the Annual Meeting will be elected to the Board. The persons named in the proxy to cast votes represented by proxies at the Annual Meeting are Matthew D. Tomazin and Cynthia M. Manuele. The proxies will vote as directed and, in the absence of instructions, will vote the shares represented by properly executed proxies in favor of the election of nominees named below.

In the event any nominee is unable or declines to serve as a director at the time of the Annual Meeting, the proxies will be voted for the nominee, if any, who may be designated by the Board, upon recommendation of the Nominating & Corporate Governance Committee, to fill the vacancy. As of the date of this Proxy Statement, the Board is not aware that any nominee is unable or will decline to serve as a director.

Shareholders may vote “for” all director nominees as a group, may “withhold” authority to vote for all director nominees as a group, or may withhold authority to vote only for specified Director nominees. A plurality of votes cast by holders of shares of common stock entitled to vote thereon is required to elect the nominees. Under a plurality vote standard, the nominees who receive the highest number of votes “for” their election will be elected. Votes to “withhold” in an uncontested election will have no effect on the outcome of the vote on Proposal No. 1. Broker non-votes will not constitute or be counted as votes cast for purposes of this Proposal, and therefore will have no impact on the outcome of this Proposal.

The Board of Directors unanimously recommends a vote “FOR” the election of each of the director nominees. Shares of common stock covered by executed proxies received by the Board will be voted “FOR” the election of each of the director nominees named below unless the shareholder specifies a different choice.

The following table sets forth each director nominee and includes such person’s name, age, gender, race/ethnicity, and whether they have been determined to be an independent director. Biographies of the director nominees follow the table. Directors Catarisano, Coletti, Fessenden, Johnson, Lee, McClurg, Rahilly, Romaine, and Spain, were elected for a one-year term expiring at the 2025 Annual Meeting. The Board of Directors affirmatively determined that Thomas R. Rochon, Jennifer R. Tegan and the nominees identified below are “independent” in accordance with Section 803A of NYSE American Company Guide. They are referred to in this Proxy Statement as the “Independent Directors.”

The following paragraphs provide information as of the date of this Proxy Statement regarding each nominee’s specific experience, qualifications, attributes and skills that led our Board to the conclusion that they should serve as a director. The information presented includes information each director has given us about positions they hold, their principal occupation and business experience for the past five years, certain non-profit boards on which they serve, and the names of other publicly-held companies of which they currently serve as a director or have served as a director during the past five years.

Nancy E. Catarisano has served as a director of the Company since 2023. She served as a Director for the Bank of Castile from July 2020 through its consolidation with Tompkins Community Bank (“TCB”) on January 1, 2022. Ms. Catarisano has served as a Community Bank Board Director for Tompkins Community Bank Western New York since the 2022 consolidation. Ms. Catarisano also serves as a Director of TCB. Ms. Catarisano joined Insero & Co., a “Top 300” full-service public accounting firm located in Rochester, New York, in 1999 and currently serves as the firm’s Managing Partner. She founded the firm’s Outsource Accounting Services Group, and provides outsource financial services to her clients that include matters relating to accounting transaction processing and cash management, strategic planning, equity and debt financings, and mergers and acquisitions. As Managing Partner, Ms. Catarisano has doubled the size of the firm. She is a Certified Public Accountant, a member of the American Institute of Certified Public Accountants, and the New York State Society of Certified Public Accountants. Ms. Catarisano serves on the Executive, Finance, Audit, and Investment Committees of the Al Sigl Community of Agencies, and is prior Chair of the agency's Board of Trustees. She is also actively involved with many different business, community, and charitable organizations across Western New York. We believe Ms. Catarisano’s qualifications to sit on our Board include her more than 20 years of public accounting experience, her active engagement with charitable organizations, and her connections to the business community in Western New York.

Janet M. Coletti has served as a director of the Company since 2024. Ms. Coletti also serves as a Director of TCB and as a Community Bank Board Director for Tompkins Community Bank Western New York. Ms. Coletti joined the Community Bank Board for Western New York in January 2023. Prior to her retirement in 2020, Ms. Coletti served as Executive Vice President and Chief Human Resources Officer of M&T Bank, a Fortune 500 company headquartered in Buffalo, New York. Ms. Coletti started her career at M&T in 1985 and held numerous positions in the Consumer Banking and Business Banking divisions before becoming Chief Human Resources Officer in 2015. Ms. Coletti was directly responsible for leading and managing M&T Bank's Human Resources functions, including recruiting, training and leadership development, compensation and benefits, diversity and inclusion, and employee engagement. She also served as a member of M&T Bank's executive management committee, which was responsible for leading all bank activities and operations. Since November 2019, Ms. Coletti has served on the board of Moog, Inc. (NYSE: MOG.A), a worldwide designer, manufacturer and systems integrator of high performance precision motion and fluid controls and controls systems for a broad range of applications in aerospace and defense and industrial markets. She also serves on the board of Culain Capital Management, a specialty finance company. Ms. Coletti is involved with many community organizations in the greater Buffalo area, including Providence Farm Collective and the Roycroft Campus Corporation. We believe Ms. Coletti's qualifications to sit on our Board include her 35 years of banking experience, public company experience as an executive and director, and her active engagement with numerous business and community organizations in the Western New York area.

Heidi M. Davidson is a first-time director nominee of the Company. Dr. Davidson has served as a Community Bank Board Director for Tompkins Community Bank Hudson Valley since January 2024. Dr. Davidson is the Chief Executive Officer of Galvanize Worldwide, a full-service marketing and communications agency that she co-founded in May 2015. From March 2011 to May 2015, Dr. Davidson was part of the turn-around team at BlackBerry Ltd in the roles of Senior Vice President of Corporate Marketing and before that Senior Vice President of Corporate Communications. Prior to BlackBerry, Dr. Davidson spent 11 years with MasterCard Worldwide, where she served in numerous leadership capacities in communications roles, compliance, global public policy, consumer education, training and events, fraud investigations, security and risk management, mergers and acquisitions, CEO transition and franchise integrity. Dr. Davidson has served as an Executive Board member of the Business Council of Westchester since May 2014. We believe Dr. Davidson’s qualifications to sit on our Board include her extensive experience in marketing, communications, crisis management, innovation, and the financial services industry and her commitment to the Hudson Valley business community.

Helen Eaton is a first-time director nominee of the Company. Ms. Eaton served as a director of Tompkins VIST Bank from November 2020 through its consolidation with TCB on January 1, 2022. She has served as a director of

the Community Bank Board for Tompkins Community Bank Pennsylvania since the consolidation. Since August 2010, Ms. Eaton has served as the Chief Executive Officer of Settlement Music School, one of the largest nonprofit community art schools in the country, with more than 250 staff and faculty providing over 11,000 weekly services to adults and children in the Greater Philadelphia region. In this role, Ms. Eaton oversees program development, funding sources, balance sheet management and the development of national and local partnerships. Prior to joining Settlement Music School, Ms. Eaton was President of Chicago Children’s Choir and Dean of Programs at the Merit School of Music in Chicago. We believe Ms. Eaton’s qualifications to sit on our Board include her experience in leadership development, strategic planning, financial management, innovation, and her commitment to the Greater Philadelphia community.

Daniel J. Fessenden has served as a director of the Company since 2009, and was elected Vice Chair of the Board in May 2024. He was a director of Tompkins Trust Company from January 2009 through its consolidation with TCB on January 1, 2022, and has served as a Director for TCB since the consolidation. Since January 2022, Mr. Fessenden has served as a Community Bank Board Director for Tompkins Community Bank Central New York, where he has served as Chair since July 2022. Mr. Fessenden served as a member of the New York State Assembly from 1993 to 1999. He has served as the Executive Director of the Fred L. Emerson Foundation, a family foundation located in Auburn, New York since January 2007. From 2004 to 2006 he served as the founding Executive Director of the Cornell Agriculture & Food Technology Park, Geneva, New York. Mr. Fessenden has been actively engaged with numerous business, civic and educational organizations throughout the Central New York region. We believe Mr. Fessenden’s qualifications to sit on our Board include his extensive experience in government and public service, his executive experience in the private sector, his active engagement with civic organizations, and his deep connections to the Central New York business community.

Patricia A. Johnson has served as a director of the Company since 2006. Ms. Johnson served as a director of Tompkins Trust Company from 2002 to 2014, and served as a director of Tompkins VIST Bank from April 2014 through its consolidation with TCB on January 1, 2022. She has served as a Director of TCB since that consolidation, and also serves as Chair of TCB’s Community Bank Board for Pennsylvania and the Pennsylvania Board Loan Committee. Ms. Johnson previously served as the Vice President for Finance and Administration with Lehigh University in Bethlehem, PA, retiring in June 2022. She had previously been with Cornell University, starting as the Assistant Treasurer in 1995, and later serving as Associate Vice President & Treasurer. Ms. Johnson has served on the boards of several regional economic development/workforce training organizations, and she has demonstrated civic leadership through her service on the boards of many local charitable or educational institutions. We believe Ms. Johnson’s qualifications to sit on our Board include her accounting expertise and her ability to understand and evaluate the Company’s complex financial operations.

Angela B. Lee has served as a director of the Company since 2023. She served as a Director of Tompkins Trust Company from December 2021 through its consolidation with TCB on January 1, 2022. She has served as a Director of Tompkins Community Bank, and also serves as a Community Bank Board Director for Tompkins Community Bank Central New York. She is Vice President, Human Resources at Baxter International, Inc. (“Baxter International”), a global public medical healthcare company, where she works to help the organization enhance a culture of inclusion and belonging across all aspects of Baxter International's business. In addition, Ms. Lee extends strategic HR support to Legal, IT, Corporate Communication and Corporate Services functions. She previously served as Vice President of Human Resources, and Chief Talent & Diversity Officer at Hill-Rom Holdings, Inc. prior to its acquisition by Baxter International in 2021. Ms. Lee has more than 25 years of experience as a human resources executive, which includes extensive business partnering skills; talent management; talent acquisition; total rewards; diversity, equity and inclusion; employee relations; and cultural integration. Ms. Lee is an active member of her community, working with civic and charitable organizations in the Central New York area. We believe Ms. Lee’s qualifications to sit on our Board include her extensive human resource experience, her work to advance inclusion initiatives, and her connections to the Central New York business and civic community.

John D. McClurg has served as a director of the Company since 2023. He served as a Director for the Bank of Castile from 1995 through its consolidation with TCB on January 1, 2022. He has served as a Director of Tompkins Community Bank, and has also served as Chair of the Community Bank Board for Tompkins Community Bank Western New York and of the Western New York Board Loan Committee. Mr. McClurg has served as president of McClurg Chrysler Dodge Jeep Ram since 1989 and McClurg Chevrolet since 1991. He has been a member of the New York State Automobile Dealers Association since 2013 and served as its Chair from 2018 to 2019. He also serves

as a member of the boards of directors for the National Auto Dealers Association and the New Car Dealers of Western NY Charitable Foundation. Mr. McClurg has served many local charitable organizations. We believe Mr. McClurg’s qualifications to sit on our Board include his deep ties to the Western New York community and his 40 plus years of experience owning and operating his own business.

Ita M. Rahilly has served as a director of the Company since 2020. She served as a director of Tompkins Mahopac Bank from 2018 through its consolidation with TCB on January 1, 2022. Since that consolidation, Ms. Rahilly has served as a Director for TCB, and as a Community Bank Board Director for Tompkins Community Bank Hudson Valley. She is the owner of Ita M. Rahilly CPA PC, and has been a Partner with the firm of RBT CPAs, LLP in Newburgh, NY since January 2005, where she is the Partner in charge of the firm’s trust estate and gift division with a focus on estates, trusts and succession planning, corporate, partnerships, international taxation, and non-profit information reporting. Ms. Rahilly is a past President of the New York State Society of Certified Public Accountants (NYSSCPA), a member of the National Association of Estate Planners and Councils, and a member of the Hudson Valley Estate Planning Council. Ms. Rahilly also serves on the board of directors of the State University of New York at New Paltz Foundation and is a member of its Audit Committee. We believe Ms. Rahilly’s qualifications to sit on our Board include her 40 years of extensive public accounting experience dealing with financial and accounting matters for complex organizations, and her deep understanding of the Hudson Valley business environment resulting from her years of working with commercial clients in the region.

Stephen S. Romaine has served as a director of the Company since May 2007 and as President and Chief Executive Officer of the Company since January 2007. He had served as President and Chief Executive Officer of Tompkins Mahopac Bank from January 2003 through December 2006. Prior to this appointment, Mr. Romaine was Executive Vice President, and Chief Financial Officer of Mahopac National Bank. In addition to the Company’s Board, Mr. Romaine serves on the TCB Board, and maintains an advisory role on TCB’s Community Bank Boards in each of its local markets. Mr. Romaine currently serves on the Board of the Federal Home Loan Bank of New York, as well as the New York Bankers Association, where he served as Chair from March 2016 through March 2017. His recent civic involvement includes service as a member of the boards of several local historical and educational institutions. We believe Mr. Romaine’s qualifications to sit on our Board include his more than 30 years as an executive in the financial services industry, including his current position as President and Chief Executive Officer of the Company.

Michael H. Spain has served as a director of the Company since 2000. Mr. Spain served as a director of Tompkins Mahopac Bank from 1992 through its consolidation with TCB on January 1, 2022 and he has served as a Director for TCB since that consolidation. He served as the Chair of the Board of Directors of Tompkins Mahopac Bank from June 2017 through its consolidation with TCB, and has served as Chair of the Community Bank Board for Tompkins Community Bank Hudson Valley (since January 2022). Mr. Spain serves as Executive Vice President of Brown & Brown of New York, Inc., d/b/a the Spain Agency, an insurance agency located in Mahopac, New York. Mr. Spain served as President of the Spain Agency from 1989 until 2015 when it became wholly owned by Brown & Brown, Inc. Mr. Spain also holds leadership positions with several privately-held real estate development companies and is involved with many charitable organizations in the Hudson Valley. We believe Mr. Spain’s qualifications to sit on our Board include his more than 20 years of service as a Tompkins Mahopac Bank Director and his extensive executive experience in the financial services industry.

The names and ages of the Company’s executive officers, including the named executive officers identified in the Summary Compensation Table in this Proxy Statement, their positions and offices held with the Company, their terms of office and experience are set forth in Part I of the Company’s Annual Report, a copy of which is included in these proxy materials.

During fiscal 2024, the Board held four regular meetings, one special meeting and three strategic planning meetings. As a matter of practice, the Independent Directors met in executive session at the end of each regular meeting for a total of four such sessions during 2024. During this period all of the directors attended more than 75% of the aggregate of the total number of meetings of the Board held during the periods that they served and the total number of meetings held by all committees of the Board on which each such director served during the period that they served.

The Board currently maintains and appoints the members of the following four standing committees: Executive, Compensation, Audit & Risk, and Nominating & Corporate Governance.

Executive Committee. The Board has adopted a written charter for the Executive Committee. A copy of the Executive Committee’s charter is posted in the “About Us - Corporate Governance” section of the Company’s website (www.tompkinsfinancial.com). The Executive Committee did not meet during fiscal 2024. The Executive Committee acts, as necessary, on behalf of the Board pursuant to the Company’s Second Amended and Restated Bylaws (the “Bylaws”).

Compensation Committee. The Board has adopted a written charter for the Compensation Committee (as used in this paragraph, the “Committee”). A copy of the Committee’s charter is posted in the “About Us - Corporate Governance” section of the Company’s website (www.tompkinsfinancial.com). The Committee met five times during fiscal 2024. The Committee reviews executive performance and approves, or recommends to the Independent Directors for approval, salaries and other matters relating to executive compensation, except that the compensation of the Chief Executive Officer is determined by the Independent Directors upon recommendation by the Committee. It also administers the Company’s equity incentive plans, including reviewing and granting equity incentive awards to executive officers and other employees. The Committee also reviews and approves various other compensation policies and matters, and is responsible for ensuring that executive officers are compensated effectively, appropriately, and in a manner consistent with the Company’s objectives. Please see the section “Role of the Compensation Committee, Management, and Consultants” below for information about this Committee’s responsibilities and activities. Each of the members of this Committee is an “Independent Director” as defined in Section 803A of the NYSE American Company Guide, and the Board has determined each committee member also meets the heightened independence standards for compensation committee members set forth in NYSE American Rule 805(c).

The members of the Company’s Compensation Committee are identified above under “Board of Directors: Committee Membership.” No member of the Compensation Committee was during fiscal 2024 or before an officer or employee of the Company or any of the Company’s subsidiaries, or had any relationship requiring disclosure under “Transactions with Related Persons” in this Proxy Statement. During 2024, no executive officer of the Company served on the board of directors or compensation committee of any other entity, one of whose executive officers served as a member of the Company’s Board of Directors or the Compensation Committee.

Audit & Risk Committee. The Board has adopted a written charter for the Audit & Risk Committee (as used in this paragraph, the “Committee”). A copy of the Committee’s charter is posted in the “About Us - Corporate Governance” section of the Company’s website (www.tompkinsfinancial.com). The Committee met nine times during fiscal 2024. This Committee assists the Board in its general oversight of accounting and financial reporting, internal controls and audit functions, and is directly responsible for the appointment, compensation and oversight of the work of the Company’s independent auditors. The responsibilities and activities of the Committee are described in greater detail in the “Report of the Audit & Risk Committee of the Board of Directors” included in this Proxy Statement. The Board has determined that Nancy E. Catarisano, Patricia A. Johnson, and Ita M. Rahilly each qualify as an “Audit Committee Financial Expert” as defined in Item 407(d) of Regulation S-K and that each of the members of the Audit & Risk Committee is an “Independent Director” as defined in Section 803A of the NYSE American Company Guide, and also satisfies the heightened independence standards applicable to Audit Committee members of Rule 10A-3 under the Securities Exchange Act of 1934, as amended (the “Exchange Act”).

Nominating & Corporate Governance Committee. The Board has adopted a written charter for the Nominating & Corporate Governance Committee (as used in this paragraph, the “Committee”). A copy of the Committee’s charter is posted in the “About Us - Corporate Governance” section of the Company’s website (www.tompkinsfinancial.com). The Committee met four times during fiscal 2024. This Committee is responsible for assisting the Board in developing corporate governance policies and practices that comply with applicable laws and regulations, including NYSE American listing standards and corporate governance requirements. The Nominating & Corporate Governance Committee is responsible for identifying, evaluating and recommending qualified candidates for election to the Board. The Committee identified first-time director nominees Heidi M. Davidson and Helen Eaton through their respective service on community bank board committees of the Board of Directors of Tompkins Community Bank and recommended them for election.

Director Qualifications. To be considered for nomination to the Board, each candidate must possess the following minimum qualifications and attributes: high personal values, judgment and integrity; an ability to understand the regulatory and policy environment in which the Company conducts its business; a demonstrated, significant engagement in one of the market areas served by the Company, based on one or more of the following within such market area—professional/business relationships, residence, and involvement with civic, cultural or charitable organizations; and experience which demonstrates an ability to deal with the key business, financial and management challenges that face financial service companies. The Company believes that such connections with one of the Company’s local communities foster ties between the Company and that community, and also allow the director to better understand the banking and financial services needs of its local stakeholders. The Nominating & Corporate Governance Committee will consider the director’s independence, qualifications and contributions and the continued need for our board to reflect a wide range of personal backgrounds and professional experience, and will balance the value brought by longer-tenured directors with the benefits of periodic refreshment of directors.

While individual experiences and qualifications serve as a baseline for consideration, the Company recognizes that the Board governs as a whole, and not as a collection of individuals. The effectiveness of the Board is not a function of the individual attributes of its members; rather, it depends on the overall chemistry of the Board. Therefore, the Nominating & Corporate Governance Committee assesses whether a particular candidate will be able to function within this broader context by evaluating their: ability to understand, and willingness to engage, the issues presented to the Board; ability to exercise prudence and judgment, but also decisiveness; and ability to effectively communicate their ideas to the other members of the Board. In the case of incumbent Directors, these assessments are made based on past experience with a particular Director and, in the case of first-time nominees, these issues are explored during the interview and vetting process described below.

Identification of Candidates & Nomination Process. At least annually, and typically on a more frequent basis, the Committee engages in a discussion to identify candidates who fulfill the criteria described above, under the heading “Director Qualifications.” The Nominating & Corporate Governance Committee will evaluate candidates who are identified by shareholders, by other members of the Board, and occasionally by members of the Company’s leadership team, which is comprised of the Company’s executive officers. To be considered, shareholder recommendations of director candidates must be received by the Chair of the Nominating & Corporate Governance Committee, Tompkins Financial Corporation, P.O. Box 460, Ithaca, NY 14851, no later than December 1^st of the year preceding the annual meeting at which such candidate is proposed to be nominated. The recommendations should include the name, address, and supporting information as to why the candidate should be considered by the Committee. The same procedures are used to evaluate all candidates, regardless of the source of the recommendation.

The Committee believes that a Board of Directors with a variety of experience, professions, perspectives, skills, and geographic representation, benefits the Company and our shareholders, and seeks nominees with these characteristics. Our directors’ broad range of skillsets and professional experiences reflects a variety of important perspectives in the boardroom, ultimately resulting in more informed decision-making. Accordingly, in identifying potential nominees, the Nominating & Corporate Governance Committee also considers whether the unique skills and professional experiences of a particular candidate adds to the depth and variety of skills and professional experiences of the Board. The Committee ensures that candidates who express interest in or are recommended as a candidate for service as a Director are included in the candidate pool from which director nominees are selected, and it employs a variety of strategies to help develop a deep candidate pool reflecting the variety of characteristics referenced above. First, the Committee strongly encourages all of our directors to identify all qualified candidates for service on our Board, and emphasizes the importance of ensuring a board culture which is welcoming to directors of all backgrounds. The Committee also recognizes the importance of recruiting candidates beyond the traditional corporate/banking arena, and thus recruits qualified candidates who work in other areas, such as non-profit organizations, in addition to candidates with traditional “corporate” backgrounds. At least annually, the Committee monitors the composition of the Board to ensure it reflects a broad range of experience, professions, perspectives, skills, and geographic representation. While not encapsulated in a written policy, the Committee and the Board stand behind these commitments to director recruiting practices.

Once the Nominating & Corporate Governance Committee has determined its interest in a potential nominee, it begins discussions with them as to their willingness to serve on the Board and one of the Company’s local market boards and, for first-time nominees, an interview will be conducted. If the nominee is an incumbent Director, the Committee will consider prior Board performance and contributions as described above; in the case of a first-time nominee, the Committee will evaluate its discussions with the candidate, and the Committee may also seek to verify its preliminary assessment of the candidate by discussing their particular attributes with other appropriate parties who have had prior professional experiences with them. At the conclusion of this process, the Committee will recommend qualified candidates that best meet the Company’s needs to the full Board, which then selects candidates to be nominated for election at the next annual meeting of shareholders. The Committee uses the same process for evaluating all candidates, whether recommended by shareholders, Directors or management. The Company expects all Board members to own at least 2,000 shares of the Company’s common stock, which shares may be accumulated over a period of three years following a Director’s initial election to the Board. Shares held in a rabbi trust as deferred stock compensation for a given Director are included in this calculation.

It is the general policy of the Board that employee directors are not paid for their service on the Board beyond their regular employee compensation. The following table sets forth the compensation paid to the Company’s non-employee directors for their service during 2024:

The Company paid non-employee directors annual fees as shown in the table below. The fees are paid in quarterly installments. Committee chair retainer fees are paid in lieu of the applicable committee retainer fees. These amounts are all included in the aggregate for each director in the table, “2024 Director Compensation,” above.

All non-employee directors’ fees paid for service on the Board were paid in cash or, if a valid election was made by the director prior to January 1, 2024, such Directors’ fees were deferred pursuant to (i) the Retainer Plan or (ii) pursuant to a Deferred Compensation Agreement.

Our Chair and our Vice Chair receive a specified annual retainer in lieu of any Board, Committee, Committee Chair, and Community Bank Board fees. In 2024, the Company paid an annual retainer to Thomas R. Rochon in the amount of $186,800 for his service as Chair of the Board, as well as his service on the Community Bank Board of Tompkins Community Bank Hudson Valley, and on the Compensation Committee and the Nominating & Corporate Governance Committee. Mr. Rochon’s retainer was paid in quarterly installments of $46,700.

During 2024, James W. Fulmer served as Vice Chair of our Board through our annual meeting of shareholders in May 2024, and Daniel J. Fessenden served as Vice Chair for the remainder of the year. For his service as Vice Chair of the Board and as a member of our Audit & Risk Committee, and for his service on the Community Bank Boards of Tompkins Community Bank Pennsylvania and Tompkins Community Bank Western New York, and on the Board of Tompkins Insurance Agencies, the Company paid Mr. Fulmer a retainer of $46,992 in two quarterly installments of $23,496.

Mr. Fessenden was elected Vice Chair of the Board effective May 2024. For his service as Vice Chair of the Board, as well as his service as Chair of the Community Bank Board and the Board Loan Committee for Tompkins Community Bank Central New York, and on the Compensation Committee and the Nominating & Corporate Governance Committee, the Company paid Mr. Fessenden a total of $110,088. Mr. Fessenden transitioned to an annual retainer fee in the second quarter following his election as Vice Chair.

The Nominating & Corporate Governance Committee recommends the amount and form of director compensation to the Company’s Board, and the Board reviews director compensation annually.

With the exception of our Chair and Vice Chair, who are paid the specified annual retainers described above, non-employee members of the Board who also sit on our Community Bank Boards and Bank Board committees receive the following annual fees shown in the table below in quarterly installments. These amounts are all included in the aggregate for each director in the “2024 Director Compensation” table above:

All retainer and other fees for service on the Company’s Board, as well as service on the Board of Directors of one or more of our subsidiaries, are payable quarterly, either in cash or, if a timely election is made by the director, in stock or deferred stock pursuant to the Retainer Plan. Non-employee directors may also elect to receive compensation in deferred cash pursuant to a Deferred Compensation Agreement.¹ If a director elects to receive deferred stock compensation under the Retainer Plan, their fees are transferred to a Rabbi Trust. The trustee acquires shares of common stock pursuant to the Company’s Dividend Reinvestment and Stock Purchase and Sale Plan. A director has no rights in or to the shares of common stock held in the Rabbi Trust until distribution is made in accordance with the Retainer Plan. An aggregate of 6,760 shares of common stock were acquired by the Rabbi Trust for the directors under the Retainer Plan in 2024, representing Board and committee fees and retainers paid and expensed in 2024.

The Board has adopted Corporate Governance Guidelines (the “Guidelines”), which reflect many of the Company’s long-standing practices, in order to strengthen our commitment to corporate governance best practices. A copy of the Guidelines is posted in the “About Us - Corporate Governance” section of our website (www.tompkinsfinancial.com). The Guidelines summarize the Company’s corporate governance practices and procedures, and the following issues, in addition to others, are covered in the Guidelines: board size; director independence; chair independence; director retirement; director resignation following a change in job responsibility; director candidate identification and nomination; director common stock ownership; responsibilities of directors; meeting attendance; executive sessions of independent directors; board committees; succession planning and management evaluation; director education; failure to receive a majority of votes cast; board assessments; and pledging/hedging policy. Under the Company’s pledging/hedging policy, as included in the Guidelines, Directors and executive officers (including their designees) are prohibited from, directly or indirectly, (1) pledging a significant number of the Company’s equity securities, or (2) hedging. “Hedging,” for purposes of the policy, includes engaging in any transaction, including the purchase of prepaid variable forward contracts, equity swaps, collars, exchange funds, put options and forward-sale contracts, which hedges or offsets, or which is designed to hedge or offset, any decrease in the market value of the Company’s equity securities (a) granted to such person as part of his or her compensation by the Company; or (b) held, directly or indirectly, by such person. Our Nominating & Corporate Governance Committee periodically reviews the Guidelines and, as necessary or appropriate, recommends changes to the Guidelines. “Significant” for purposes of the policy means more than the lesser of (1) 1,000 shares and (2) 20% of the Company’s equity securities beneficially owned by such person.

A majority of the Board and all members of the Audit & Risk Committee, Compensation Committee, and Nominating & Corporate Governance Committee are “independent,” as affirmatively determined by the Board, consistent with the criteria established by NYSE American and as required by our Bylaws.

The Board has conducted an annual review of director independence for all nominees for election as directors. During this review, the Board considered transactions and relationships during the preceding three years between each Director or nominee or any member of their family and the Company, and its executive officers, subsidiaries, affiliates and principal shareholders, including those transactions and relationships described below under “Transactions with Related Persons.” The purpose of this review was to determine whether any such relationships or transactions were inconsistent with a determination that the Director is independent.

As a result of this review, the Board affirmatively determined that the directors identified as “Independent” in the table on page 4 meet the standards of independence described above.

The Board, under the leadership of the Nominating & Corporate Governance Committee, conducts annual self-evaluations to determine whether the Board and its committees are functioning effectively and in the best interests of the Company and its shareholders. Through this process, the Board also assesses board composition by evaluating the qualifications, skills and experience of the directors on the Board. As part of this annual self-assessment, directors are able to provide feedback on the performance of other directors. A summary of the results of the annual Board self-assessment and the individual self-assessments are reviewed by the Nominating & Corporate Governance Committee and the Board.

Shareholders may communicate with the Board by writing to the following address: Board of Directors, Tompkins Financial Corporation, P.O. Box 460, Ithaca, NY 14851. All such communications from shareholders will be reviewed by the Chair of the Board or the Chair of the Nominating & Corporate Governance Committee, each of whom is an Independent Director, and, if they determine that a communication should be reviewed by the full Board, it will be presented to the Board for review and consideration.

The Board strongly encourages the attendance of all directors at annual meetings of shareholders. The 2024 Annual Meeting of Shareholders was held on May 14, 2024 and all of the Company’s thirteen directors were in attendance.

The Board has adopted the Tompkins Financial Corporation Code of Ethics for the Chief Executive Officer and Senior Financial Officers, which applies to the Company’s Chief Executive Officer, Chief Financial Officer, and Chief Accounting Officer. A copy of the Code of Ethics is available in the “About Us - Corporate Governance” section of the Company’s website (www.tompkinsfinancial.com). The Company will post material amendments to or waivers from the Code of Ethics for the Chief Executive Officer and Senior Financial Officers at this location on its website.

Presently, the roles of Chief Executive Officer and Chair of the Board are separate, as the Board feels this model offers advantages of including additional input and a range of prior experience within our leadership structure. However, no single leadership model is right for the Company at all times, and the Board does not have a policy that these roles will always be separate. The Board recognizes that other leadership models can be appropriate for the Company, given different circumstances.

The Board has an active role, both at the full Board and also at the committee level, in overseeing management of the Company’s risks. The Board regularly reviews information regarding cybersecurity, asset quality, capital, securities portfolio, liquidity, operations and other matters, as well as the risks associated with each. The Compensation Committee oversees risks associated with compensation arrangements and the Audit & Risk Committee oversees management of cybersecurity and financial risks. The Board’s role in the risk oversight process has not directly impacted its leadership structure.

The Board is committed to ongoing director education. Our Nominating & Corporate Governance Committee maintains a list of pertinent topics, including topics on which our directors have specifically requested additional information, and a different topic is typically covered at each Board meeting. In addition, directors connect professional experiences and development or training opportunities from their full-time occupations, where relevant, to their work on the Board. These experiences are shared with fellow directors.

The Board’s Nominating & Corporate Governance Committee reviews and provides oversight with respect to the Company’s strategy and initiatives related to environmental, social and governance matters (“ESG”). The Committee remains informed of the key ESG paradigms, and provides updates to the Board regarding the Company’s ESG practices. The Company’s stated core values include, among other things, integrity, community impact, sustainable excellence, and a commitment to and from our employees. The Company is committed to conducting its business in a manner which aligns with our core values and which creates long-term value for our shareholders, communities, and Company. More information about our ESG practices can be found on our website (www.tompkinsfinancial.com/corporate-social-responsibility). Please note that information found on such website is not part of, nor incorporated by reference into, this Proxy Statement.

The Board’s Compensation Committee also considers risk and its influence on the Company’s compensation programs. This Committee reviews each compensation element individually and all compensation elements in the aggregate to ensure that the overall compensation program provides a balanced perspective that ultimately aligns pay with performance while also ensuring bonus/incentive programs do not motivate inappropriate risk-taking. Equity award levels and practices are set to foster shared interests between management and shareholders, but are not considered by the Committee to be at levels that would drive inappropriate behavior. In the Committee’s judgment, the compensation policies and practices of the Company do not give rise to material risks.

The Compensation Committee has also adopted a “clawback” policy which provides for the recoupment of certain compensation paid to our executive officers in the event of an accounting restatement resulting from material noncompliance with financial reporting requirements under the federal securities laws, as described in more detail under the heading “Compensation Forfeiture & Recovery” on page 26. In addition, any award agreement provides that the participant’s rights under an award are subject to alteration or reduction upon the occurrence of certain events, including, but not limited to, a breach of restrictive covenants or conduct that is detrimental to the business or reputation of the Company.

In addition, we are subject to guidance issued by our primary banking regulators designed to ensure that incentive compensation arrangements at banking organizations appropriately tie rewards to longer-term performance and do not undermine the safety and soundness of the firm or create undue risks to the financial system. This guidance embodies three core principles, which are: (1) incentive compensation arrangements at a banking organization should provide employees incentives that appropriately balance risk and financial results in a manner that does not encourage employees to expose their organizations to imprudent risks; (2) these arrangements should be compatible with effective controls and risk management, and (3) these arrangements should be supported by strong corporate governance, including active and effective oversight by the organization’s board of directors. We believe that our incentive compensation programs are in compliance with this guidance.

The Company has adopted an insider trading policy that governs transactions in our securities by directors, executive officers and employees of the Company and its subsidiaries. The Company believes that its insider trading policy is reasonably designed to promote compliance with insider trading laws, rules, and regulations. A copy of our insider trading policy is filed as Exhibit 19 to our Annual Report on Form 10-K for the fiscal year ended December 31, 2024.

The following tables set forth certain information, as of March 17, 2025, with respect to the beneficial ownership of our common stock by: (1) each shareholder known by the Company to be the beneficial owner of more than 5% of the Company’s common stock; (2) each director and nominee; (3) each executive officer named in the Summary Compensation Table, below; and (4) all executive officers and Directors as a group. Except as otherwise indicated, each of the shareholders named below has sole voting and investment power with respect to the outstanding shares of common stock beneficially owned.

As of March 17, 2025, no person or group was known by the Company to be the beneficial owner of more than 5% of the outstanding shares of the Company’s common stock, except as follows:

The primary goal of the Committee is to offer executive compensation that is fair and reasonable, and is consistent with the Company’s size, the compensation practices of the financial services industry in general, and the current economic climate. The key objectives of our compensation program are to attract, develop, and retain high caliber executives who are capable of maximizing the Company’s performance over the long term for the benefit of its shareholders. The Committee rewards long-term value creation, and considers a number of performance factors when setting executive compensation as described in further detail in this Compensation Discussion and Analysis.

The Board of Directors of the Company (the “Board”) has delegated to the Compensation Committee (the “Committee”) the responsibility for determining or recommending to the Independent Directors of the Board the compensation of the Company’s executive officers, including the executive officers identified in the tables below (the “Named Executive Officers”). For 2024, the Company's Named Executive Officers were:

When determining the compensation of its Named Executive Officers, the Committee considers the Company’s financial performance, a desire to retain key executives by ensuring each component of compensation is competitive, and the individual contributions of each Named Executive Officer. The Company’s net income for fiscal 2024 was up as compared to fiscal 2023, due in large part to the execution of the Company’s strategic initiatives. The Company saw broad based growth across the business, with increasing loan and deposit balances and higher levels of fee-based revenues. In addition, the Company further supported the growth in net income through expense management. In 2024 the Company reduced expenses by 1.8% as compared to 2023. In recognition of these factors, the following actions were approved with respect to 2024 compensation:

These elements of compensation, as well as the Committee’s process in making compensation recommendations, are described in greater detail below.

The Committee is responsible for general oversight of personnel policies for the Company and its subsidiaries, including review and administration of non-qualified deferred compensation, administrative and non-fiduciary aspects of retirement and supplemental executive retirement plans, long-term equity compensation, and executive compensation plans. Each of the members of this Committee is an “Independent Director” as defined in Section 803A of the NYSE American Company Guide, and also meets the heightened independence standards for compensation committee members set forth in NYSE American Rule 805(c).

The Committee makes recommendations concerning the compensation of our Named Executive Officers, and those recommendations are reviewed and approved by our Independent Directors; however, equity awards are granted solely by the Committee, as the designated administrator of our equity incentive plans. The Independent Directors, under the leadership of our independent Chair, are responsible for establishing the annual performance goals and objectives of the Chief Executive Officer and evaluating his performance in light of such goals and objectives. Executive officers do not play a role in determining their own compensation, but they are called on to make recommendations concerning those individuals that report to them, including an assessment of performance. The Company’s Chief Executive Officer makes recommendations to the Committee regarding the compensation of the Named Executive Officers that report to him. The President of Tompkins Community Bank makes recommendations to the Committee regarding the compensation of bank local market presidents, including Mr. DeMilia. Additionally, the Committee reviews the competitiveness of the Company’s compensation programs, and oversees the succession planning process for executive officers, other than the Chief Executive Officer, for whom succession planning is conducted at the full Board level. The Committee also discusses and considers the results of the shareholders’ advisory vote when making decisions on the compensation paid to our Named Executive Officers and potential changes to such compensation, as discussed further below. As permitted by law and by the rules of the NYSE American, the Committee may delegate all or a portion of its duties and responsibilities to a subcommittee of the Committee.

The Compensation Committee has the authority to retain outside counsel, experts, and other advisors as it determines appropriate to assist it in the full performance of its functions. Since July 2022, the Committee has retained the services of AON Human Capital Solutions, a division of Aon, plc as a compensation consultant (the “Compensation Consultant”). During 2023, the Committee engaged the Compensation Consultant to assist the Committee in developing a new Benchmarking Peer Group to be used with respect to 2024 and future compensation decisions and to complete a compensation study of executive compensation based on the new Benchmarking Peer Group. The Compensation Consultant also provided the Committee with advice regarding goal achievement with respect to the vesting of performance-based restricted stock.

The Committee has assessed the independence of the Compensation Consultant pursuant to SEC rules and exchange requirements, and has concluded that no conflict of interest exists that would impair the Compensation Consultant’s ability to independently provide services to the Compensation Committee.

In furtherance of its objective to attract, develop and retain high caliber executives who are capable of maximizing the Company’s performance for the benefit of its shareholders, the Committee periodically compares its compensation levels, practices, and financial performance to survey and publicly available data for a group of banking institutions of similar size, geographic market or structure (the “Benchmarking Peer Group”). Based on the recommendations provided by the Compensation Consultant, the Committee approved a new Benchmarking Peer Group for 2024, which included the following financial institutions:

The updated Benchmarking Peer Group generally includes bank holding companies headquartered in the Northeast and Middle Atlantic regions of the United States with assets at December 31, 2022 of $5 billion to $13 billion. Information from comparative groups is only one factor in the Committee’s assessment of appropriate compensation levels, policies, and practices. The Committee does not have a formal policy of targeting a certain

percentile of the market data but considers market data in establishing the mix of compensation (including the allocation between cash and non-cash compensation and short and long-term equity compensation). The Committee does not have a formal policy regarding the relationship between compensation levels provided to the Chief Executive Officer and other Named Executive Officers.

The Committee considers individual performance based on the Named Executive Officer's specific contributions to the Company's strategic and financial results, as well as the development of the executive’s leadership knowledge and skills. Each Named Executive Officer has responsibility for one or more of our business units or divisions, and the Committee considers the overall success of the applicable business unit/division when it makes compensation decisions for that executive.

While advisory votes on executive compensation (“say-on-pay votes”) are non-binding, the Committee values the input of investors. In 2024, the Company's shareholders approved, on an advisory basis, the compensation paid to our Named Executive Officers by a vote of 96.69%. The Committee did not make changes to executive compensation based on these results. However, based on an analysis of the 2023 say-on-pay vote, the Committee, with the guidance of the Compensation Consultant, revised its short-term incentive program for 2024 to include pre-determined goals for corporate and individual performance, instead of awarding a discretionary bonus after a review of year-end results. At the Annual Meeting, shareholders are again being asked to approve, on an advisory basis, the compensation paid to our Named Executive Officers. See “Proposal No. 2 – Advisory Vote on Executive Compensation,” below.

The major components of the Company’s executive officer compensation are: (i) base salary, (ii) short-term incentive awards, (iii) long-term, equity-based awards, and (iv) retirement and other benefits.

Base Salary. The Company’s base salary program is designed to recognize the roles and responsibilities of executive officers’ positions and their performance in those roles. The Committee annually reviews the salaries of the Company’s executives. When setting base salary levels for recommendation to the Independent Directors, the Committee typically considers (a) competitive market conditions for executive compensation including the Benchmarking Peer Group, (b) the Company’s ability to provide merit adjustments to its employees, including NEOs and (c) the individual’s performance with respect to their business unit and demonstrated leadership.

For 2024, the Committee set a merit budget for all employees based on a review of comparative survey data, turnover rates, local unemployment data for the geographic regions in which the Company operates, and the Company's historical merit budgets. Based on a review of the data, the Committee established a 3% merit budget for 2024 and recommended increases generally ranging from 0% to 4%.

In 2024, most of the Company’s employees received salary increases, including each of the Named Executive Officers, as shown in the table below.

In determining the base salary increases for the Named Executive Officers for 2024, the Committee considered the merit budget, individual performance, and the results of a comparative executive compensation study performed by the Committee's Compensation Consultant and presented to the Committee in January 2024. The Committee recommended an increase of 8.00% for Mr. Tomazin based on his exceeding expectations during his first six months in his role as Chief Financial Officer and because his base salary was below the median for his position in the Company's Benchmarking Peer Group. Mr. McKenna received an increase of 4.00% due to bank performance in a challenging interest rate environment and to bring his base salary closer to the market median for the Company's Benchmarking Peer Group.

Short-Term Incentive Awards. The Company's Incentive Plan is a performance-based variable compensation program tied to the achievement of specific performance metrics and strategic goals. It is designed to motivate and reward selected senior officers, including the NEOs, for their contributions to the Company's growth, profitability and overall success. Under the Incentive Plan, the NEOs are eligible to receive cash awards based on pre-established corporate and individual performance goals. For 2024, the Committee set target incentives as a percentage of base salary for each NEO.

The target short-term incentive and weightings for corporate and individual performance for each NEO are set forth below:

In January 2025, the Committee determined the short-term incentive payouts for each of our executives (including our Named Executive Officers) based on its review of corporate and individual performance achievement for 2024.

Corporate Performance. In assessing corporate performance, the Committee set performance goals based on the Company’s Core earnings per share (“EPS”), Core revenue per share, and Core pre-tax pre-provision net revenue (“PPNR”) per share (each with equal weighting). The Committee chose these performance metrics which are financial measures not prepared in accordance with U.S. generally accepted accounting principles (“non-GAAP”) because they measure both top- and bottom-line performance. The Committee chose non-GAAP Core metrics to focus on operating performance and exclude unusual and non-recurring items. The Core metrics below exclude gains and losses on sales of securities and restructuring costs. PPNR provides a measure of profitability which is neutral to the impact of asset quality and taxes. Based on the 2024 results shown below, the Committee determined that corporate performance was achieved at a level of 100%.

Individual Performance. The Committee measured individual performance against the Named Executive Officers’ achievement of their individual goals, which were established for each of them at the beginning of 2024. The Compensation Committee evaluated the Named Executive Officers for their individual performance as follows:

Stephen S. Romaine, President and Chief Executive Officer: Mr. Romaine received a 100% award under the individual performance component in recognition of his strong efforts at leading the Company. His individual performance goals included broad responsibility for executing our strategic plan with a particular focus on growth in revenue and containment of expenses. The Company's expectations included successful oversight of leadership succession in light of retirements at the senior leadership level, and the development of a cohesive and effective leadership team with a number of new members.

Matthew D. Tomazin, Chief Financial Officer: Mr. Tomazin received a 95% award under the individual performance component. Mr. Tomazin’s individual performance goals included work on our long-term, sustainable earnings performance, including in-depth peer analysis and planning. He was also tasked with reviewing strategic investment opportunities, creating a broader view of operating budgets throughout the company and further developing the skill levels of our finance staff.

John M. McKenna, President Tompkins Community Bank: Mr. McKenna received a 90% award under the individual performance component. His individual goals included a focus on the business development and earnings performance of our banking business, expanded and upgraded business development staff recruiting, assessing expanded business opportunities, and communication among his business lines and others.

David S. Boyce, President & CEO, Tompkins Insurance Agencies (“TIA”): Mr. Boyce received a 95% award under the individual performance component. Mr. Boyce’s individual performance goals included succession planning in our insurance business, sustainable growth and earnings performance, as well as ongoing development of a long-term strategy for our insurance business.

David M. DeMilia, President Tompkins Community Bank Hudson Valley: Mr. DeMilia received a 95% award under the individual performance component. Mr. DeMilia’s individual performance goals included achievement of deposit and loan objectives in our Hudson Valley market, further refinement of strategy on pricing, achieving cost of funds goals, expanding business development staff in the Hudson Valley, along with work on personal development.

Short-Term Incentive Achievement. Based on the review of corporate and individual performance described above, the Committee determined the Named Executive Officers achieved their goals at the following levels:

The table below shows how the target incentive opportunity amount compared to the incentive payments actually made based on the Compensation Committee’s goal weightings and assessment of the corporate and individual performance for each NEO.

Long-Term, Equity-Based Awards. In November 2024, the Named Executive Officers each received equity awards with performance-based and time-based vesting. The number and type of awards granted to each Named Executive Officer are set forth below.

Performance-Based Awards. The Committee grants RSUs to promote executive retention and incentivize the Named Executive Officers to achieve long-term performance goals that create shareholder value and are earned if the specified financial goal is met at the end of the performance period. For 2024, the Committee granted performance-based awards in the form of restricted stock units (“RSUs”). These RSUs will vest in shares of the Company’s common stock subject to the Company’s achievement of performance goals over the period beginning on January 1, 2025 and ending on December 31, 2027 (the “performance period”).

The shares of common stock underlying the RSUs will vest at the target level if the average of the Company’s return on average equity (“ROAE”) for each year over the performance period is greater than or equal to the average of the Federal Reserve Board (“FRB”) Peer Group’s ROAE reported at the 50^th percentile for each year during the performance period. The maximum performance goal will be met if (1) the average of the Company’s ROAE for each year over the performance period is greater than or equal to the average of the FRB Peer Group’s ROAE for each year during the performance period and (2) the Company achieves a 10% average increase in Core EPS during the performance period. The Company's FRB Peer Group is the group of companies included in the FRB’s Bank Holding Company Performance Report (“BHCPR”), Peer Group 2, which covers banks and bank holding companies with assets between $3 billion and $10 billion. ROAE is shown in the BHCPR as Net Income/Average Equity Capital. Core EPS means net income attributable to Tompkins Financial Corporation before extraordinary items, and less net gain or loss on the sale of securities and nonrecurring items, expressed on a diluted per share basis. The Committee evaluates performance achievement after the FRB releases the BHCPR for the fourth quarter of the last fiscal year of the performance period.

In evaluating whether performance conditions are met, the Committee may consider adjustments to exclude the effect of certain transactions, extraordinary or non-recurring items, or accounting changes. After receiving advice from the Compensation Consultant, in 2024 the Committee made adjustments to the Company's ROAE in determining whether the performance goal was achieved with respect to Mr. Romaine's performance-based restricted stock for the 2021-2023 performance period. The Company's sale of securities in 2023 at a loss, which was undertaken to improve the Company’s future results, caused the Company's ROAE performance goal to be missed. Therefore, in order to avoid penalizing Mr. Romaine for supporting longer-term strategic decisions that might result in short-term losses, the Committee determined to exclude the loss on the sale of the securities and other non-recurring items from the Company's ROAE calculation. For more information regarding these adjustments, see the “2024 Option Exercises and Stock Vested” table below.

If one of our NEOs meets certain eligibility requirements and retires prior to the expiration of the performance period, the NEO will remain eligible to receive the shares covered by their award so long as the performance goal is attained, subject to the NEO’s compliance with a three-year non-competition agreement.

Time-Based Awards. The time-based awards were granted in restricted stock and are subject to a five-year vesting schedule. This schedule provides for zero percent vesting in year one and 25% vesting in years two through five. The Committee granted these awards to promote executive retention and alignment of our executives’ interests with shareholders.

More information about the terms and conditions of these grants is available in the “Grants of Plan-Based Awards” table and related narrative.

The Company chooses to award equity-based compensation because such grants (1) align executive interests with shareholder interests by creating a direct link between compensation and shareholder return, (2) give executives a significant, long-term interest in the Company’s success and (3) help retain key executives in a competitive market for executive talent. While the Committee recognizes that the executives of the Company can exert very little influence on short-term fluctuations in stock price, the Committee does believe that long-term stock price appreciation reflects achievement of strategic goals and objectives. Equity awards are granted based on the Named Executive Officers’ roles and their anticipated contribution to the achievement of the Company’s strategic goals and objectives. The Committee typically grants equity awards in November each year. Time-based awards typically vest over a five (5) year period, and the Committee has historically referenced a three (3) year performance period for performance-based grants.

In determining how to structure the 2024 equity awards, the Committee considered information and recommendations provided by the Compensation Consultant with respect to performance-based awards for a number of executives including the Named Executive Officers. The value of equity awards granted to our Named Executive Officers helps to ensure that their total compensation levels remain competitive with peers.

Retirement and Other Benefits. The Company maintains several programs that are designed to assist Company employees with their long-term retirement planning. The majority of Company employees, including the Named Executive Officers, are eligible to participate in the Company’s 401(k) Plan and ESOP. The Committee believes that, in addition to providing retirement income, these plans have the added benefit of linking compensation to the Company’s stock performance. The Company also maintains defined contribution and defined benefit pension plans.

401(k) Plan. The 401(k) Plan is a profit-sharing plan with a salary deferral arrangement that meets the requirements of Section 401(k) of the Internal Revenue Code of 1986, as amended (the “Internal Revenue Code”). Pursuant to the 401(k) Plan, an employee may defer a portion of base pay, within limits specified in the 401(k) Plan. For 2024, the Company matched 100% of an employee’s contribution up to 2% of the employee’s base pay. The Company also provided an additional employer contribution of 2% of the employee’s base pay. In addition, substantially all employees of the Company and its subsidiaries who were first employed before July 2023, including the Named Executive Officers, are eligible to receive an annual discretionary Company contribution to the 401(k) Plan based on age and length of service. These discretionary contributions are subject to a three-year vesting period. Certain employees, including Messrs. McKenna and DeMilia, who participated in the Tompkins Financial Corporation 2015 Defined Contribution Plan as of November 30, 2021 receive a contribution to the 401(k) Plan at an increased level based on age and length of service. The contribution for 2024 for Messrs. McKenna and DeMilia are included as “All Other Compensation” in the Summary Compensation Table below, and described in Note 5 to that table.

Profit-Sharing. Substantially all employees of the Company and its subsidiaries, including the Named Executive Officers, are eligible to receive an annual cash profit-sharing payment. Employees may elect to defer all or a portion of their profit-sharing cash payment to the 401(k) Plan (which deferral is not eligible for matching by the Company). Eligible compensation used to determine profit sharing contributions is limited to the annual IRS mandated compensation limit ($345,000 for 2024). However, the Company pays a “supplemental profit sharing” amount as current cash compensation to the Named Executive Officers which represents the profit sharing attributable to their compensation in excess of the IRS-mandated compensation limit under Section 415 of the Internal Revenue Code (the “Code Section 415 Limit”).The profit-sharing and supplemental profit-sharing cash component amounts for the Named Executive Officers are included as “All Other Compensation” in the Summary Compensation Table below, and described in Note 5 to that table.

Employee Stock Ownership Plan. The purpose of the ESOP is to permit the Company to make discretionary profit-sharing contributions to employees in the form of shares of common stock of the Company in order to facilitate stock ownership by employees. The Company's Board of Directors determines the contributions, which are limited to a maximum amount as stipulated in the ESOP. In January 2025, the Board determined that an ESOP contribution of 2% of each employee’s base pay would be made for 2024.

Pension Plan. The Company has a defined benefit pension plan, called the Tompkins Financial Corporation Retirement Plan (the “Pension Plan”), which covers substantially all employees of the Company and its subsidiaries who were employed prior to January 1, 2010. The Pension Plan does not require or allow employee contributions. The assets of the Pension Plan are held in a separate trust, which for 2024 was administered by the Retirement Plans Management Committee. On January 1, 2010, in order to more effectively control the volatility of plan expense, the

Company closed the Pension Plan to new employees. On July 31, 2015, the Pension Plan was frozen, and active participants in this plan ceased to earn an accrued benefit after this date (the “Pension Plan Freeze”). Messrs. Romaine, Boyce, McKenna and DeMilia are all participants in the Pension Plan.

Supplemental Executive Retirement Plans (“SERPs”). The Company is a party to non-qualified supplemental retirement plans with certain of its executive officers, including each Named Executive Officer other than Mr. Tomazin. These plans provide additional retirement income to promote retention and to recognize and reward long-term service to the Company. In connection with the Pension Plan Freeze, the Company amended and restated the existing SERPs with Messrs. Romaine, McKenna and Boyce (the “Amended SERPs”) and entered into new defined benefit SERPs (the “DB SERPs”) with Messrs. Romaine and Boyce. In 2019, the Company further amended Mr. Romaine’s SERP to expand the definition of “Earnings” under the SERP to better align the scope of compensation included in our CEO's retirement benefits with chief executive compensation in a manner that is more consistent with market practice. All benefits provided under the SERPs are unfunded and the Company makes payments directly to plan participants. The Pension Plan and SERPs are further described in the narrative following the “Pension Benefits” table, below.

Mr. McKenna also participates in a defined contribution SERP (the “DC SERP”), into which the Company makes contributions that would otherwise be limited due to the Code Section 415 Limit. Mr. DeMilia participates in a DC SERP into which the Company makes an annual contribution of 16% of his annual base salary. The DC SERPs are further described in the narrative following the “2024 Nonqualified Deferred Compensation” table, below.

Deferred Compensation Plan. The Company maintains a nonqualified deferred compensation plan for a select group of officers, including the Named Executive Officers. This plan allows participating officers to defer receipt of all or a portion of cash bonuses/incentives, profit-sharing payments and supplemental profit-sharing payments. Amounts deferred under the deferred compensation plan on the part of the Named Executive Officers are included as “Bonus”, “Non-Equity Incentive Plan Compensation” or “All Other Compensation,” as applicable, in the Summary Compensation Table and in the “2024 Nonqualified Deferred Compensation Table” below.

Life Insurance Benefits. As a part of its comprehensive and competitive approach to compensation, the Company provides life insurance benefits to certain officers of the Company, including all of the Named Executive Officers. For Messrs. Romaine and Boyce, the Company has entered into split dollar life insurance agreements. These insurance contracts are carried at cash surrender value on the Company’s consolidated statements of financial condition. Increases in the cash surrender value of the insurance are reflected as noninterest income, and the related mortality expense is recognized as other employee benefits expense in the Company’s consolidated statements of income. The value of premiums paid with respect to such life insurance on behalf of the Named Executive Officers is included as “All Other Compensation” in the Summary Compensation Table. The split dollar agreements for Messrs. Romaine and Boyce establish a minimum death benefit payable to each executive under his plan and a maximum payment equal to the lesser of (a) four times the executive’s base annual salary (as defined in the applicable plan), or (b) the death benefit or benefits available under the Policy or Policies (as defined in the applicable plan) maintained as of the date of such executive’s death. Messrs. McKenna, Tomazin, and DeMilia are entitled to a Group Term Life benefit of two times their base annual salary.

Post-Retirement Life Insurance. The Company offers post-retirement life insurance coverage to Messrs. Romaine, McKenna and Boyce. This insurance includes split dollar agreements for Messrs. Romaine and Boyce and a group-term benefit for Mr. McKenna.

Perquisites. Perquisites for the Named Executive Officers are limited to personal use of a Company-owned vehicle and an opportunity for partial reimbursement of club membership dues. The Committee believes that these limited benefits assist the Named Executive Officers in the performance of their duties by providing convenience in light of the significant demands on our Named Executive Officers’ time, including frequent car travel on business and providing a place for business development activities. Messrs. McKenna and DeMilia received partial reimbursement for their club memberships. Other Named Executive Officers have declined this perquisite.

Termination of Employment and Change-in-Control Arrangements. The Company does not have employment contracts with the Named Executive Officers and does not maintain a severance plan that covers the Named Executive Officers. However, the Company is obligated to provide certain payments to the Named Executive Officers upon termination as part of their SERPs. In addition, under the Company’s equity incentive plans, outstanding unvested equity awards may fully vest if a Named Executive Officer is terminated in connection with a change of

control of the Company. SERP payments, accelerated vesting of equity awards and other benefits due upon termination are explained under the “Potential Payments upon Termination or Change in Control” section of this Proxy Statement. In the change-in-control context, these payments and benefits are subject to a “double trigger” as described in greater detail under that section.

Long-Term Disability Benefits. As a part of its comprehensive and competitive approach to compensation, all Named Executive Officers participate in the Group Long-Term Disability Plan. In addition, the Company maintains Executive Individual Disability Insurance to provide additional income that is more in line with the executive’s total compensation in the event an Executive becomes disabled. Total annual disability benefits are shown in the chart on page 39.

The Compensation Committee has adopted the Tompkins Financial Corporation Amended and Restated Clawback Policy to recover incentive-based executive compensation in connection with accounting restatements due to material non-compliance with federal securities laws. The policy is intended to comply with the rules adopted by the Securities and Exchange Commission and the NYSE American, LLC. The Company's right to recover excess incentive compensation provided by this policy are in addition to any other remedies available to the Company under applicable law, policy or agreement including, without limitation, those rights described under Section 304 of the Sarbanes Oxley Act.

In addition, the 2019 Equity Incentive Plan allows the Compensation Committee to specify in any award agreement with our executives (including our Named Executive Officers) that the executive’s rights under an award are subject to alteration or reduction upon the occurrence of certain events, including, but not limited to, a breach of restrictive covenants or conduct that is detrimental to the business or reputation of the Company. We have included such a provision in each of the award agreements covering grants of equity incentive compensation to our Named Executive Officers.

Tompkins Financial Corporation aims to compensate its executive officers competitively for their performance while also mitigating potential risks for the Company. Management and the Board have been careful to mitigate many of the risks of incentive programs, choosing to reward proven results based on performance that is not tied to one specific metric, but instead is based on the achievement of a combination of individual, division, business unit, and corporate financial goals, as described herein. The result is that no individual or group is incentivized to take unnecessary risk with respect to a customer, the organization or our shareholders. We believe that these efforts are supported by an effective risk management system and strong corporate governance.

As described above under “Corporate Governance Matters – Corporate Governance Guidelines,” the Guidelines include a policy prohibiting non-employee directors and executive officers, including the Named Executive Officers, from hedging the economic risk of their ownership of the Company’s equity securities or from pledging more than the lesser of (1) 1,000 shares and (2) 20% of the Company's equity securities beneficially owned by such person.

The accounting and tax treatment of compensation generally has not been a significant factor in determining the amounts of compensation for our executive officers. However, the Compensation Committee and management have considered the accounting and tax impact of various program designs to balance the potential cost to the Company with the benefit and value to the executive.

Section 162(m) of the Internal Revenue Code generally denies publicly-held corporations a federal income tax deduction for compensation exceeding $1,000,000 paid to the chief executive officer, chief financial officer or any of the three other highest paid executive officers.

While the tax impact of any compensation arrangement is one factor to be considered, that impact is evaluated in light of the Committee’s overall compensation philosophy and objectives. Accordingly, the Committee may award compensation to the Company’s executive officers that is not fully deductible if it determines the compensation is consistent with its philosophy and is in the Company’s and its shareholders’ best interests.

Section 409A of the Internal Revenue Code imposes an additional tax on certain forms of deferred compensation. The Committee takes Section 409A into account in determining the form and timing of compensation paid to the Company’s executives.

The Company values equity incentive awards in accordance with FASB ASC Topic 718. More information regarding the application of ASC Topic 718 by the Company may be found in Note 11 (Stock Plans and Stock--Based Compensation) to the Company’s audited financial statements filed with the SEC in the Company’s Annual Report on Form 10-K for the fiscal year ended December 31, 2024.

The information contained in this report shall not be deemed to be “soliciting material” or “filed” or incorporated by reference in future filings with the SEC, or subject to the liabilities of Section 18 of the Exchange Act, except to the extent that the Company specifically requests that it be treated as soliciting material or specifically incorporates it by reference into a document filed under the Securities Act or the Exchange Act.

The Compensation Committee has reviewed and discussed the “Compensation Discussion and Analysis” with the management of the Company. Based on the Compensation Committee’s review and discussion, the Committee recommended to the Board that the “Compensation Discussion and Analysis” be included in this Proxy Statement and incorporated by reference into the Company’s 2024 Annual Report on Form 10-K.

The following table sets forth information concerning the total compensation earned by the Company’s Chief Executive Officer, the Chief Financial Officer, and the next three most highly-compensated executive officers of the Company in the fiscal year ended December 31, 2024. These five officers are referred to as the “Named Executive Officers” in this Proxy Statement.