SEC Form DEF 14A filed by Trupanion Inc.

A LETTER TO OUR STOCKHOLDERS

April 30, 2025

Dear Trupanion Stockholders,

I am pleased to address you as the Chairperson of Trupanion and cordially invite you to attend the 2025 Annual Meeting of Stockholders (the Annual Meeting) of Trupanion, Inc. (the Company or Trupanion).

I am incredibly proud of the foundation Trupanion now has, the fortification of our balance sheet, and the improved capital position. This puts the company in a place of strength with so much compounding growth and opportunity ahead. The most impactful metric of all is the $3.5 billion paid directly to veterinarians on behalf of our pet-loving members. This milestone is a powerful reflection of Trupanion’s commitment to helping pets receive the best care possible and supporting the families who love them.

The Annual Meeting will be held on Wednesday, June 11, 2025 at 9 a.m. (Pacific Time), at 6100 4th Avenue South, Seattle, Washington 98108. For specific instructions on how to vote your shares, please refer to the information provided in this proxy statement. We urge all stockholders to vote their shares in advance of the meeting through the Internet, mail or by telephone. If you plan to attend the meeting, you must request an admission ticket by May 15, 2025 by following the instructions in this proxy statement.

Please note that, like last year, we will not be holding our stockholder engagement event following the Annual Meeting. Instead, we will be hosting an Investor Day on September 17, 2025, at which we will have presentations by management and an extensive question and answer period. This annual event is designed to be the best opportunity to understand Trupanion’s achievements and challenges over the past year and its strategic vision going forward. Those looking for opportunities to engage in Q&A and connect real-time with the team are encouraged to attend the Investor Day. Additional details regarding this event are available at https://investors.trupanion.com/news/events/default.aspx.

In the event any changes to our Annual Meeting plans are necessary or appropriate, such as the date or location (including to hold the meeting by remote communication), we will announce the change in advance and post details, including instructions on how stockholders can participate, on our investor relations website at https://investors.trupanion.com and file them with the Securities and Exchange Commission (the SEC).

We continue to elect to deliver our proxy materials to the majority of our stockholders over the Internet, which provides stockholders with the information they need, while minimizing our environmental impact and lowering the distribution cost of proxy materials. On or around May 2, 2025, we expect to commence delivery to stockholders of a Notice of Internet Availability of Proxy Materials (Notice of Internet Availability) containing instructions on how to:

The matters to be acted upon at the meeting are described in the accompanying Notice of Annual Meeting of Stockholders and proxy statement.

Your vote is important to us. We encourage you to vote as soon as possible. Whether or not you plan to attend the Annual Meeting in-person, please vote your shares through the Internet, by mail, or by phone to ensure your shares are represented at the meeting. For those who plan to attend in-person, you will also have the opportunity to vote at the Annual Meeting. If you plan to attend the meeting, you must request an admission ticket by May 15, 2025 by following the instructions in this proxy statement.

Thank you for your continued support and trust in Trupanion. In our 2024 Shareholder letter, our CEO & President, Margi Tooth, will share detailed insights into our performance, strategic initiatives, and future outlook. Margi’s leadership and vision have been instrumental in driving our success, and I have complete confidence and admiration for the team. Together, we will continue to make a positive impact on the lives of pets and their families for decades to come.

Warm Regards,

Darryl Rawlings

Chairperson of the Board of Directors

Seattle, Washington

NOTICE OF ANNUAL MEETING OF STOCKHOLDER

Notice of Annual Meeting of Stockholders
		DATE:				TIME:				LOCATION:
		June 11, 2025				9:00 a.m. PDT				6100 4th Avenue South
										Seattle, Washington 98108

Agenda. We are holding the Annual Meeting for the following purposes, which are more fully described in the accompanying proxy statement:

Record Date. Only stockholders of record at the close of business on April 16, 2025 are entitled to notice of, and to vote at, the Annual Meeting and any adjournments thereof. For ten days prior to the Annual Meeting, a complete list of the stockholders entitled to vote at the Annual Meeting will be available for examination by any stockholder for any purpose relating to the Annual Meeting during ordinary business hours at our headquarters, provided, stockholders will need to comply with Company policies in connection with visiting our headquarters.

Stock Ownership. For questions regarding your stock ownership, contact Trupanion’s Director of Investor Relations, Gil Melchior, by email at [email protected]. If you are a registered holder, contact our transfer agent, Broadridge Corporate Issuer Solutions, Inc., by phone at (877) 830-4936 or by email through their website at https://shareholder.broadridge.com/bcis/.

Digital Proxy Statement and Annual Report. Visit https://investors.trupanion.com/financials/annual-reports/default.aspx to review or download a digital copy of this proxy statement and our Annual Report.

YOUR VOTE IS VERY IMPORTANT. Although you are legally entitled to attend the Annual Meeting in-person for the purposes of voting your shares, we recommend you vote your shares by proxy in advance of the Annual Meeting through the Internet, by mail or by telephone to ensure that your shares are represented at the meeting. For specific instructions on how to vote your shares, please refer to the information provided in this proxy statement. If you plan to attend the meeting, you must request an admission ticket by May 15, 2025 by following the instructions in this proxy statement.

Please note that we will not be holding our stockholder engagement event following the Annual Meeting. Instead, we will be hosting an Investor Day on September 17, 2025, at which we will have presentations by management and an extensive question and answer period. This annual event is designed to be the best opportunity to understand Trupanion’s achievements and challenges over the past year and its strategic vision

going forward. Those looking for opportunities to engage in Q&A and connect real-time with the team are encouraged to attend the Investor Day. Additional details regarding this event are available at https://investors.trupanion.com/news/events/default.aspx.

TABLE OF CONTENTS

Proxy Statement Summary

Information About Solicitation and Voting

The accompanying proxy is solicited on behalf of Trupanion, Inc.’s Board of Directors for use at Trupanion’s 2025 Annual Meeting to be held on Wednesday, June 11, 2025, at 9:00 a.m., Pacific Time, and any adjournment or postponement thereof. The Annual Meeting will be held in-person at 6100 4th Avenue South, Seattle, Washington 98108 and stockholders will be able to attend the Annual Meeting and vote during the meeting in-person. However, we encourage stockholders to vote in advance of the Annual Meeting through the Internet, by mail or by telephone to ensure that your shares are represented at the Annual Meeting. If you plan to attend the meeting, you must request an admission ticket by May 15, 2025 by following the instructions in this proxy statement.

At the Annual Meeting, stockholders will act upon the proposals described in this proxy statement. In addition, we will consider any other matters that are properly presented for a vote at the Annual Meeting. We are not aware of any other matters to be submitted for consideration at the Annual Meeting. If any other matters are properly presented for a vote at the meeting, the persons named in the proxy, who are officers of the Company, have the authority in their discretion to vote the shares represented by the proxy.

Annual Meeting Agenda and Voting Recommendations

1

General Proxy Information

Record Date; Quorum

Only holders of record of our common stock at the close of business on April 16, 2025, the record date, will be entitled to vote at the Annual Meeting. At the close of business on April 16, 2025, Trupanion had 42,776,104 shares of common stock outstanding and entitled to vote.

The holders of a majority of the voting power of the shares of stock entitled to vote at the Annual Meeting as of the record date must be present or represented by proxy at the meeting in order to hold the Annual Meeting and conduct business. This presence is called a quorum. Your shares are counted as present at the Annual Meeting if you are present and vote in-person at the meeting or if you have properly submitted a proxy through the Internet, mail or by telephone.

Internet Availability of Proxy Materials

Under rules adopted by the SEC, we are furnishing proxy materials to our stockholders primarily via the Internet, instead of mailing printed copies to each stockholder. On or around May 2, 2025, we expect to commence delivery to our stockholders of a Notice of Internet Availability of Proxy Materials (Notice of Internet Availability) containing instructions on how to access our proxy materials, including our proxy statement and our Annual Report on Form 10-K for the year ended December 31, 2024. The Notice of Internet Availability also provides instructions on how to vote through the Internet or by telephone and includes instructions on how to receive paper copies of the proxy materials by mail or an electronic copy of the proxy materials by email.

This process is designed to reduce our environmental impact and lower the costs of printing and distributing our proxy materials without impacting our stockholders’ timely access to this important information. However, if you would prefer to receive printed proxy materials, please follow the instructions included in the Notice of Internet Availability.

Voting Rights; Required Vote

Each holder of shares of our common stock is entitled to one vote in respect of all matters at the Annual Meeting for each share of common stock held as of the close of business on April 16, 2025, the record date. You may vote all shares owned by you at such date, including shares held directly in your name as the stockholder of record and shares held for you as the beneficial owner in street name through a brokerage firm, bank, or other nominee. Dissenters’ rights are not applicable to any of the matters being voted on.

How Your Shares Are Voted

Stockholder of Record: Shares Registered in Your Name. If on April 16, 2025, your shares were registered directly in your name with Trupanion’s transfer agent, Broadridge Corporate Issuer Solutions, Inc., then you are considered the stockholder of record with respect to those shares. As a stockholder of record, you may vote at the Annual Meeting, vote in advance through the Internet, by telephone, or if you request to receive paper proxy materials by mail, by filling out and returning a proxy card appointing a person to represent you and vote your shares at the Annual Meeting.

Beneficial Owner: Shares Registered in the Name of a Brokerage Firm, Bank or Other Nominee. If on April 16, 2025, your shares were held in an account with a brokerage firm, bank or other nominee, then you are the beneficial owner of the shares held in street name. As a beneficial owner, you have the right to direct your brokerage firm, bank or other nominee on how to vote the shares held in your account, and your brokerage firm, bank or other nominee provides voting instructions for you to use in directing it on how to vote your shares. Because the brokerage firm, bank or other nominee that holds your shares is the stockholder of record, if you

2

wish to attend the Annual Meeting and vote your shares, you must, in addition to following the instructions set forth in this proxy statement to obtain a ticket, obtain a valid proxy from the firm that holds your shares giving you the right to vote the shares at the Annual Meeting.

A proxy submitted by a stockholder may indicate that the shares represented by the proxy are not being voted with respect to the election of directors (stockholder withholding). Stockholder withholding will count for purposes of determining the presence of a quorum, but it will not be treated as a vote cast. Accordingly, stockholder withholding will have no effect on the election of the nine director nominees named in this proxy statement. Similarly, abstentions will count for purposes of determining the presence of a quorum, but they will not be treated as votes cast, and, therefore, will have no effect on the ratification of the appointment of Ernst & Young LLP or the advisory votes to approve the compensation provided to our named executive officers in 2024 or the frequency of future advisory votes on the compensation provided to our named executive officers. In addition, while a broker has discretion to vote uninstructed shares held in street name on “routine” matters, under stock market rules, a broker lacks discretion to vote shares held in street name on “non-routine” matters in the absence of instructions from the beneficial owner of the stock (called a broker non-vote). Proposal 2 is a routine matter, but Proposals 1, 3, and 4 are non-routine matters. Broker non-votes will count for purposes of determining the presence of a quorum, but will not be treated as votes cast on Proposals 1, 3, and 4. Accordingly, broker non-votes will have no effect on the election of directors or the advisory votes to approve compensation provided to our named executive officers in 2024 or the frequency of future advisory votes on the compensation provided to our named executive officers.

The following chart describes the proposals to be considered at the Annual Meeting, our recommended vote with respect to each matter, the vote required to approve each matter, and the manner in which votes will be counted:

Voting Instructions; Voting of Proxies

If you are a stockholder of record, you may:

3

Votes submitted through the Internet, by mail, or by telephone must be received by 11:59 p.m., Eastern Time, on June 10, 2025. Submitting your proxy, through these means will not affect your right to vote in person should you decide to attend the Annual Meeting.

You may vote shares held directly in your name as the stockholder of record in person at the Annual Meeting. If you choose to vote your shares in person at the Annual Meeting and you are a record holder, then you must bring your admission ticket (which you may obtain as described below) and government-issued identification such as a driver’s license or passport. You may also appoint another person to represent you at the Annual Meeting through a written, signed proxy giving such person the right to vote the shares. Such person must bring that proxy, their government-issued identification and an admission ticket to the Annual Meeting.

If you are not the stockholder of record, please refer to the voting instructions provided by your brokerage firm, bank or other nominee to direct it how to vote your shares.

For Proposal 1, you may either vote “FOR” each of the nominees to the Board of Directors, or you may withhold your vote from any nominee you specify. For Proposals 2 and 3, you may vote “FOR” or “AGAINST” or “ABSTAIN” from voting. For Proposal 4, you may vote “1 YEAR”, “2 YEARS”, or “3 YEARS”, or you may “ABSTAIN” from voting. Your vote is important. Whether or not you plan to attend the Annual Meeting in-person, we urge you to vote in advance of the meeting through the Internet, by mail or by phone to ensure that your shares are represented at the meeting.

All proxies will be voted in accordance with the instructions specified on the proxy card. If you sign a physical proxy card and return it without instructions as to how your shares should be voted on a particular proposal at the Annual Meeting, your shares will be voted in accordance with the recommendations of our Board of

4

Directors stated in the section above titled “How Your Shares Are Voted.” The proxies also confer discretionary authority upon the person named therein with respect to any amendments, variations or other matters which may properly come before the Annual Meeting. As of the date hereof, the Company knows of no such amendments, variations or other matters to come before the Annual Meeting. However, if any such amendment, variation or other matter properly comes before the Annual Meeting, a proxy, when properly completed and delivered and not revoked, will confer discretionary authority upon the person named therein to vote on such other business in accordance with their best judgment, subject to any limitations imposed by applicable law or the rules of any applicable securities exchange.

If you received a Notice of Internet Availability, please follow the instructions included on the notice on how to access your proxy card and vote through the Internet or by telephone.

If you receive more than one proxy card or Notice of Internet Availability, your shares are registered in more than one name or are registered in different accounts. To make certain all of your shares are voted, please follow the instructions included on the Notice of Internet Availability on how to access and vote each proxy card.

Expenses of Soliciting Proxies

The expenses of soliciting proxies will be paid by Trupanion. Following the original distribution and mailing of the solicitation materials, we or our agents may solicit proxies by mail, email, telephone, or by other similar means, or in-person. Our directors, officers and other employees, without additional compensation, may solicit proxies for us personally or in writing, by mail, email, telephone, or by other similar means. Following the original distribution and mailing of the solicitation materials, we will request brokerage firms, banks and other nominees who are record holders to forward copies of those materials to persons for whom they hold shares and to request authority for the exercise of proxies. In such cases, we, upon the request of the record holders, will reimburse such holders for their reasonable expenses. If you choose to access the proxy materials and/or vote through the Internet, by phone or by mail, you are responsible for any Internet access, telephone or data usage or postage charges you may incur.

Revocability of Proxies

A stockholder of record who has given a proxy may revoke it at any time before the closing of the polls by the inspector of elections at the Annual Meeting by:

Please note, however, that if your shares are held of record by a brokerage firm, bank or other nominee and you wish to revoke a proxy, you must contact that firm to revoke or change any prior voting instructions.

Electronic Access to the Proxy Materials

The Notice of Internet Availability will provide you with instructions regarding how to:

5

To help us achieve our environmental goals, consider choosing to receive your future proxy materials by email, which will reduce the impact of our annual meetings of stockholders on the environment and lower the costs of printing and distributing our proxy materials. If you choose to receive future proxy materials by email, you will receive an email next year with instructions containing a link to those materials and a link to the proxy voting site. Your election to receive proxy materials by email will remain in effect until you terminate it.

Voting Results

Voting results will be tabulated and certified by the inspector of elections appointed for the meeting. The preliminary voting results will be announced at the meeting. The final results will be tallied by the inspector of elections and filed with the SEC in a current report on Form 8-K within four business days of the Annual Meeting.

6

Proposal No. 1: Election of Directors

As of the date of this Proxy Statement, our Board of Directors consists of nine directors.

Our nominating and corporate governance committee has nominated, Max Brodén, Jacqueline “Jackie” Davidson, Paulette Dodson, Richard Enthoven, Murray Low, Elizabeth “Betsy” McLaughlin, Darryl Rawlings, Howard Rubin, and Margaret “Margi” Tooth for election as directors at the 2025 Annual Meeting, and at the recommendation of our nominating and corporate governance committee, our Board of Directors proposes that Mr. Brodén, Ms. Davidson, Ms. Dodson, Mr. Enthoven, Dr. Low, Ms. McLaughlin, Mr. Rawlings, Mr. Rubin, and Ms. Tooth each be elected as a director for a one-year term expiring at the 2026 annual meeting and until their successor is duly elected and qualified or until their earlier resignation or removal.

Our nominating and corporate governance committee regularly considers and will continue to assess Board size, tenure and refreshment, and whether our Board of Directors has the right mix of skills, qualifications and experiences. We believe our Board size of nine is appropriate at this time.

Under our Bylaws, each director is elected by a plurality of the votes cast at the Annual Meeting. This means that the nine individuals nominated for election to the Board of Directors at the Annual Meeting receiving the highest number of “FOR” votes will be elected. You may either vote “FOR” any or all of the nominees or you may “WITHHOLD” your vote with respect to any or all nominees. Shares represented by proxies will be voted “FOR” the election of each of the nominees, unless the proxy is marked to withhold authority to so vote. You may not cumulate votes in the election of directors. If any nominee for any reason is unable to serve, the proxies may be voted for such substitute nominees as the proxy holders, who are officers of our Company, might determine. Each nominee has consented to being named in this proxy statement and to serve if elected. Proxies may not be voted for more than eight directors.

7

Our Board of Directors

Board of Directors Snapshot

Our Board of Directors and their respective ages as of April 16, 2025 are as follows:

Information regarding our director nominees (see Proposal 1), including their principal occupations, certain other directorships they hold, or have held, and their other skills and qualifications, is set forth below. There are no familial relationships among our directors and officers. No director nominee has an arrangement or understanding with another person under which he or she was or is to be selected as a director or nominee.

Our Directors and Nominees

8

9

10

11

12

Non-Employee Director Compensation

Non-Employee Director Compensation Program

We maintain a non-employee director compensation program. For calendar year 2024, each of our non-employee directors received an annual retainer in the amount of $150,000. In addition, any non-employee directors serving as the lead independent director or as the chairs of each of the Board of Directors, audit committee, compensation committee and nominating and corporate governance committee received an additional annual retainer in the amount of $50,000. Annual amounts are pro-rated for any person whose service commences after the applicable amounts are paid.

Under our non-employee director compensation program, a director receives their retainer in the form of (i) restricted stock units (RSUs) or non-qualified stock options, as our Board of Directors determines each year and/or (ii) cash, subject to certain limitations. Directors may elect to receive (i) 50% of their retainer in cash and 50% in equity or (ii) 100% in cash if the director holds at least the minimum amount of equity required under our stock ownership guidelines (without regard to the five-year transition relief), unless otherwise approved by the compensation committee. Annual awards that are unvested terminate at the time a non-employee director’s service ends, and, in general, no cash compensation will be paid following the effective date of a director’s resignation or other termination from our Board of Directors.

For 2024, the number of shares of common stock underlying RSU grants was determined by dividing the applicable dollar amount by the value of a share of common stock as reported by the NASDAQ stock market as of the first day of the applicable open trading window in which the grant was made. If equity had been in the form of non-qualified stock options, the number of underlying shares of common stock would have been determined by dividing the applicable dollar amount by the value of each option calculated using the Black-Scholes valuation method as of the first day of the open trading window in which the grant was made.

For calendar year 2024, our Board of Directors determined that the equity portion of non-employee director retainers would be in the form of RSUs. Max Brodén and Betsy McLaughlin elected to receive their retainers in RSUs only. Dan Levitan and Zay Satchu, whose terms as directors each ended in June 2024, elected to receive their retainers in RSUs only as well. Jackie Davidson and Paulette Dodson each elected to receive 50% of their retainer in cash and 50% in the form of RSUs. Murray Low, Howard Rubin, and Richard Enthoven each elected to receive their retainers in cash only. Following Mr. Rawlings’ resignation as chief executive officer on August 1, 2024, he was eligible to receive compensation as a non-employee director and chairman of the Board of Directors and elected to receive his retainer in cash only.

Under our non-employee director compensation program in effect for 2024, equity awards were granted in the first open trading window of the calendar year and vested in four quarterly installments on March 31^st, June 30^th, September 30^th, and December 31^st, subject to the continued service of the non-employee director through the vesting date. Similarly, any cash amounts were paid in the same quarterly installments, subject to the continued service of the non-employee director on each date.

In November 2024, we amended our non-employee director compensation program in order to (i) align our annual determination of director compensation with the actual length of directors’ terms (i.e. from the date of each shareholder meeting until the following year shareholder meeting) rather than a calendar year, and (ii) allow non-employee directors to defer settlement of their RSUs until they leave our board. Under this revised program, equity awards will be granted in the open trading window immediately prior to our annual meeting of stockholders and will vest in four quarterly installments in each successive open trading window, subject to the continued service of the non-employee director through the vesting date. Similarly, any cash amounts will be paid in the same quarterly installments, subject to the continued service of the non-employee director on each date. (To account for this change in annual cadence, the revised program also provides for a prorated retainer to compensate our directors for their service between January 1, 2025 and the open trading window immediately prior to our 2025 annual meeting of stockholders.) Finally, the RSU deferral provision permits each

13

director to elect to defer settlement of their RSUs until such director ceases to provide services to Trupanion. In general, directors must make these deferral elections in the calendar year prior to the date of the grant of such RSUs. Directors who make a deferral election will have no right as stockholders with respect to amounts credited to their deferred RSU accounts until such RSUs are settled. Settlement of any RSUs credited to the deferred RSU account in shares of fully vested common stock will occur as soon as practicable following the director’s termination of service.

Additional Compensation for Non-Employee Directors

From time to time, our Board of Directors may also award additional compensation to directors when it determines doing so is in our best interests and those of our stockholders, such as for unexpected or additional service contributions.

In 2024, in recognition of their service on the Board of Directors through our 2024 annual meeting of stockholders, we paid Dan Levitan and Zay Satchu, directors who did not stand for reelection at the 2024 annual meeting, $37,500 each in cash. We made this payment because they had equity awards granted in early 2024 that expired following their departure from the Board, and they therefore did not receive compensation under such awards to account for the latter portion of their 2024 service as a board member. We have since adjusted the annual period for director compensation as described above to align with the actual length of directors’ terms (i.e. from the date of each shareholder meeting until the following year shareholder meeting) rather than a calendar year.

Further, in 2024, following his resignation as an employee, we paid non-employee director Darryl Rawlings $83,333 in consideration for consulting services in connection with our pet food initiative, pursuant to a consulting agreement we entered into with Mr. Rawlings.

As part of his service to our Board of Directors, Howard Rubin also serves on the boards of directors of American Pet Insurance Company, GPIC Insurance Company, and ZPIC Insurance Company, and, in 2024, served on the board of directors of QPIC Insurance, each wholly-owned subsidiaries of Trupanion. In consideration of his service as a director of these subsidiaries, Mr. Rubin received an annual retainer, paid in the form of RSUs, with a value of $15,000 for each board on which he served. For 2024, the number of RSUs granted for this service was determined by dividing $30,000 by our then-most current calculation of intrinsic value of a share of our common stock.

The Company also provides reimbursement for reasonable travel, accommodation and out-of-pocket expenses of directors to attend Board meetings and participate in other corporate functions.

2024 Non-Employee Director Compensation Table

The following table presents the total compensation for each person who served as a non-employee member of our Board of Directors during the year ended December 31, 2024. Other than as set forth in the table, during the year ended December 31, 2024, we did not pay any fees to, make any equity awards or non-equity awards to, or pay any other compensation to the non-employee members of our Board of Directors, with the exception of reimbursement of travel expenses as described above. Margi Tooth, our current Chief Executive Officer, received no compensation for her service as a director during the year ended December 31, 2024. Darryl Rawlings, our former Chief Executive Officer, likewise did not receive any compensation for his service as a director for the portion of the year that he also served as an employee. The compensation provided to Mr. Rawlings and Ms. Tooth as employees is discussed in the section entitled “Executive Compensation”.

14

15

Corporate Governance

We are strongly committed to good corporate governance practices. These practices provide an important framework within which our Board of Directors and management pursue our strategic objectives for the benefit of our stockholders.

Corporate Governance Guidelines

Our Board of Directors has adopted Corporate Governance Guidelines that set forth expectations for directors, director independence standards, the board committee structure and functions and other policies for the governance of our Company. Our Corporate Governance Guidelines are available on the investor relations section of our website at https://investors.trupanion.com. Information contained on, or that can be accessed through, our website is not incorporated by reference, and you should not consider information on our website to be part of, this proxy statement.

Board Composition and Leadership Structure

Under our Corporate Governance Guidelines, our Board of Directors is free to choose its chairperson in any way that it deems best for us. Our Board of Directors, in consultation with our nominating and corporate governance committee, periodically considers its leadership structure and may change the structure as it deems appropriate. From January 2023 until July 2024, the positions of Chief Executive Officer and Chairperson of our Board of Directors were held by Mr. Rawlings. Our Board of Directors determined that having our Chief Executive Officer as chairperson of the Board of Directors facilitated our Board of Directors’ decision-making process because Mr. Rawlings has first-hand knowledge of our operations and the major opportunities and challenges facing us. This also enabled Mr. Rawlings to act as the key link between our Board of Directors and other members of management. To assure effective independent oversight, our Corporate Governance Guidelines provide that when the positions of Chairperson of our Board of Directors and Chief Executive Officer are held by the same person, our independent directors may designate a Lead Independent Director and Dr. Low served in this role. Following Mr. Rawlings’ resignation and Ms. Tooth’s appointment as our Chief Executive Officer, the positions of Chief Executive Officer and Chairperson of our Board of Directors were again held by different people. This structure allows our Chief Executive Officer to focus on our business strategy and operations while our Chairperson leads our Board of Directors in advising and independently overseeing management. At this time, our Board of Directors believes such separation functions adequately, providing incrementally enhanced oversight of management by our Board of Directors. In addition, Dr. Low continues to serve as our Lead Independent Director.

Board’s Role in Risk Oversight

Our Board of Directors believes that open communication between management and the Board of Directors is essential for effective risk management and oversight. In addition to receiving regular Company performance reports, our Board of Directors meets with our Chief Executive Officer and other members of the senior management team at least quarterly at Board of Directors meetings, where, among other topics, they discuss strategy, key performance metrics, and risks in the context of reports from the management team and evaluate the risks inherent in our business and significant transactions. While our Board of Directors is ultimately responsible for risk oversight, our Board committees assist the Board of Directors in fulfilling its oversight responsibilities in certain areas of risk. Among other things, the audit committee assists our Board of Directors in fulfilling its oversight responsibilities with respect to risk management in the areas of internal control over financial reporting, disclosure controls and procedures and cybersecurity. The compensation committee assists our Board of Directors in assessing whether Trupanion’s executive compensation programs and policies are competitive, aligned with stockholder interest and designed to avoid undue or excessive risk-taking. The nominating and corporate governance committee assists our Board of Directors in fulfilling its oversight responsibilities with respect to the management of risk associated with Board membership and corporate governance.

16

Director Independence

Our common stock is listed on the NASDAQ Global Market. Under the rules of the NASDAQ Stock Market, independent directors must comprise a majority of a listed company’s board of directors. In addition, the rules of the NASDAQ Stock Market require that, subject to specified exceptions, each member of a listed company’s audit, compensation and nominating and corporate governance committees be independent. Under the rules of the NASDAQ Stock Market, a director will only qualify as an “independent director” if, in the opinion of that company’s board of directors, that person does not have a relationship that would interfere with the exercise of independent judgment in carrying out the responsibilities of a director.

Audit committee members must also satisfy the heightened independence criteria set forth in Rule 10A-3 under the Exchange Act. In order to be considered independent for purposes of Rule 10A-3, a member of an audit committee of a listed company may not, other than in their capacity as a member of the board of directors or any board committee: (i) accept, directly or indirectly, any consulting, advisory or other compensatory fee from the listed company or any of its subsidiaries or (ii) be an affiliated person of the listed company or any of its subsidiaries. Compensation committee members are also subject to heightened independence standards similar to those applicable to audit committee members.

Our Board of Directors has undertaken a review of the independence of each director and considered whether each director has a relationship with us that would interfere with their ability to exercise independent judgment in carrying out their responsibilities. As a result of this review, our Board of Directors determined that Mr. Brodén, Ms. Davidson, Ms. Dodson, Mr. Enthoven, Dr. Low, Ms. McLaughlin, and Mr. Rubin, representing seven of our nine directors, are “independent directors” as defined under the applicable rules of the SEC and the listing requirements and rules of the NASDAQ Stock Market. Our Board of Directors also determined that Mr. Levitan and Dr. Satchu, directors whose terms ended as of our 2024 annual meeting of stockholders, were independent under such rules and listing requirements.

Our Board of Directors did not conclude that Mr. Rawlings was independent because he recently served as our Chief Executive Officer and is currently providing consulting services to us. Our Board of Directors also did not conclude that Ms. Tooth was independent because she currently serves as our Chief Executive Officer.

In determining independence, our Board of Directors considered the mandatory non-independence tests in NASDAQ Rule 5605(a)(2)(A)-(F) and various other transactions, relationships and arrangements involving our directors. Mr. Rubin was an executive officer of ours more than ten years ago and he also formerly provided certain consulting services to us. Ms. McLaughlin also formerly provided certain consulting services to us prior to her appointment to our Board of Directors. Mr. Brodén currently serves as the Chief Financial Officer of Aflac Incorporated, with whom we entered into a Strategic Alliance Agreement and certain related agreements and who owns more than 5% of our common stock. Our Board of Directors also considered the beneficial ownership of our common stock by directors and by entities with whom directors have relationships (even if the director does not control the entity), such as TARMAC DLTFM Limited, an entity affiliated with Mr. Enthoven, which has, in the past, disclosed that it is the beneficial owner of more than 5% of our common stock. Our Board of Directors has determined that none of these transactions, relationships or arrangements affect the independence of Messrs. Rubin, Brodén, Enthoven or Ms. McLaughlin.

In making these determinations, our Board of Directors reviewed and discussed information provided by the directors and the Company regarding each director’s business and personal activities and relationships as they may relate to us and our management, including the beneficial ownership of our capital stock by each director and other transactions involving them.

17

Role of Lead Independent Director

Dr. Low, in his role as our Lead Independent Director, works to ensure that “all voices are heard” within the boardroom, proactively spends time with our Chief Executive Officer to understand our vision and strategy, and helps focus our Board of Directors on areas aligned with our vision and strategy. In addition to acting as the chairperson of the independent director sessions, the Lead Independent Director also assists our Board of Directors in supporting effective corporate governance.

Our Lead Independent Director supports the Chairperson of our Board in scheduling and setting the agenda for meetings of our Board of Directors and, when the Chairperson of our Board of Directors is not present, the Lead Independent Director may chair such meetings. In addition, the Lead Independent Director may preside over executive sessions of independent directors, serve as a liaison between the Chairperson of our Board of Directors and the independent directors, coordinate information sent to our Board of Directors, approve meeting schedules to ensure sufficient time to cover all agenda items, consult with stockholders on an annual basis and perform such other functions and responsibilities as requested by our Board of Directors from time to time.

Committees of Our Board of Directors

Our Board of Directors has established an audit committee, a compensation committee and a nominating and corporate governance committee, each of which has a charter. The composition and responsibilities of each committee are described below. Members serve on these committees until their resignations or until otherwise determined by the Board of Directors. Copies of the charters for each committee are available without charge on the investor relations website at https://investors.trupanion.com/governance/Committee-Charters-Governance-Documents/default.aspx. As of April 30, 2025, the Company’s committee composition is as follows:

Name

Independent

Chairperson of the Board

Lead Independent Director

Audit Committee

Compensation Committee

Nominating and Corporate Governance Committee

Darryl Rawlings

Margi Tooth

Max Brodén

✓

Jacqueline “Jackie” Davidson

✓

Paulette Dodson

✓

Richard Enthoven

✓

Murray Low

✓

Elizabeth “Betsy” McLaughlin

✓

Howeard Rubin

✓

✓ = “Independent”  = “Chair” or “Lead Independent Director”  = “Committee Member”

18

Audit Committee

Our audit committee consists of Mr. Brodén, Ms. Davidson, and Mr. Rubin, with Ms. Davidson serving as the chair of our audit committee. The composition of our audit committee meets the independence and other composition requirements under the applicable NASDAQ Stock Market and SEC rules and each member of our audit committee is financially literate. In addition, our Board of Directors has determined that each member of our audit committee is an “audit committee financial expert” as defined in Item 407(d)(5)(ii) of Regulation S-K promulgated under the Securities Act. Our audit committee’s principal functions are to assist our Board of Directors in its oversight of:

Compensation Committee

Our compensation committee consists of Mr. Enthoven, Ms. McLaughlin, and Mr. Rubin, with Mr. Rubin serving as chair of our compensation committee. The composition of our compensation committee meets the requirements for independence under the applicable NASDAQ Stock Market and SEC rules. Our compensation committee’s principal functions are to assist our Board of Directors with respect to compensation matters, including:

Nominating and Corporate Governance Committee

Our nominating and corporate governance committee consists of Ms. Dodson, Dr. Low, and Ms. McLaughlin, with Ms. Dodson serving as chair of our nominating and corporate governance committee. Each nominating and corporate governance committee member is independent under the applicable NASDAQ Stock Market rules and SEC rules. Our nominating and corporate governance committee’s principal functions include:

Corporate Governance and Ethics Principles

A primary goal of our Board of Directors is to build long-term value for our stockholders. Our Board of Directors has adopted and follows corporate governance practices that it and our senior management believe are sound and, promote this purpose, including the establishment of the following:

19

Insurance Company. In addition, more than ten years ago, Mr. Rubin served as our Chief Operating Officer. None of our executive officers currently serves or has served on the Board of Directors or compensation committee of any entity whose executive officers included any of our directors.

Board and Committee Meetings, Attendance, and Executive Sessions

The Board of Directors and its committees meet regularly throughout the year and also hold special meetings and act by written consent from time to time. During 2024:

During 2024, no director attended fewer than 75% of the aggregate of the number of meetings held by our Board of Directors. No director attended fewer than 75% of the number of meetings held by all committees of our Board of Directors on which such director served, in each case during the time the director served on our Board of Directors.

Typically, in conjunction with the regularly scheduled meetings of our Board of Directors, the directors meet in executive sessions with our Chief Executive Officer outside the presence of other members of management and, separately, our non-employee directors meet outside the presence of the Chief Executive Officer. In 2024, our Lead Independent Director, Dr. Low, presided over such executive sessions.

Board Attendance at Annual Stockholders’ Meeting

We invite and encourage each member of our Board of Directors to attend our annual meetings of stockholders though we do not have a formal policy regarding attendance of annual meetings by the members of our Board of Directors. We may consider in the future whether our Company should adopt a more formal policy regarding director attendance at our annual meetings. Nine of our ten then-current directors attended our 2024 Annual Meeting of Stockholders.

Role of Stockholder Engagement

Our Board of Directors believes it is important to regularly engage with our stockholders. In the past several years, we have proactively reached out to many of our largest stockholders to solicit their feedback on our executive compensation, corporate governance and disclosure practices in order to gain a better understanding of the practices they most value. Our stockholder engagement team has consisted of certain independent directors and members of our investor relations and legal team. Stockholders have also regularly met with members of our senior management team to discuss our strategy and review our operational performance.

Communication with Directors

Stockholders and interested parties who wish to communicate with our Board of Directors, non-employee members of our Board of Directors as a group, a committee of our Board of Directors or a specific member of our Board of Directors (including our Chairperson and Lead Independent Director) may do so by letters addressed to the attention of our Corporate Secretary, Trupanion, Inc., 6100 4th Avenue South, Suite 200, Seattle, Washington 98108.

21

All communications are reviewed by our Corporate Secretary and provided to the members of our Board of Directors unless such communications are sales materials or other routine items, or items unrelated to the duties and responsibilities of our Board of Directors.

Considerations in Evaluating Director Nominees

Our nominating and corporate governance committee is responsible for identifying, evaluating and recommending nominees to our Board of Directors. A variety of methods are used to identify and evaluate director nominees, with the goal of maintaining and further developing a diverse, experienced and highly qualified Board of Directors. Candidates may come to our attention through current members of our Board of Directors, professional search firms, stockholders or other persons.

Our nominating and corporate governance committee will recommend to our Board of Directors for selection all nominees to be proposed by our Board of Directors for election by the stockholders, including approval or recommendation of a slate of director nominees to be proposed by our Board of Directors for election at each annual meeting of stockholders, and will recommend all director nominees to be appointed by our Board of Directors to fill interim director vacancies.

Our Board of Directors encourages selection of directors who will contribute to our overall corporate mission. The nominating and corporate governance committee may from time to time review and recommend to our Board of Directors the desired qualifications, expertise and characteristics of directors, including such factors as business experience, diversity and professional experience in management, animal health, technology, finance, marketing, financial reporting and other areas that are expected to contribute to an effective Board of Directors. In evaluating potential candidates for our Board of Directors, the nominating and corporate governance committee considers these factors, among others, in the light of the specific needs of our Board of Directors at that time. We value diversity on a company-wide basis but have not adopted a policy regarding board diversity.

In addition, under our Corporate Governance Guidelines, a director is expected to spend the time and effort necessary to properly discharge such director’s responsibilities. Accordingly, a director is expected to regularly attend meetings of the Board of Directors and committees on which such director sits and to review materials distributed to the director. Thus, the number of other public company boards and other boards (or comparable governing bodies) on which a prospective nominee is a member, as well as their other professional responsibilities, will be considered. Under our Corporate Governance Guidelines, there are no limits on the number of terms that may be served by a director. However, in connection with evaluating recommendations for nomination for reelection, the nominating and corporate governance committee considers director tenure.

Stockholder Recommendations for Nominations to the Board of Directors

Our nominating and corporate governance committee will consider properly submitted stockholder recommendations for candidates for our Board of Directors who meet the minimum qualifications as described above. Our nominating and corporate governance committee does not intend to alter the manner in which it evaluates candidates, including the minimum criteria set forth above, based on whether or not the candidate was recommended by a stockholder. A stockholder of record can nominate a candidate for election to our Board of Directors by complying with the procedures in Article I, Section 1.11 of our Amended and Restated Bylaws. Any eligible stockholder who wishes to submit a nomination should review the requirements in our Bylaws on nominations by stockholders. Any nomination should be sent in writing to our Corporate Secretary, Trupanion, Inc., 6100 4th Avenue South, Suite 200, Seattle, Washington 98108. Submissions must include the full name of the proposed nominee, complete biographical information, a description of the proposed nominee’s qualifications as a director, and other information specified in our Bylaws. Any such submission must be accompanied by the written consent of the proposed nominee to be named as a nominee and to serve as a director if elected. These candidates are evaluated at meetings of the nominating and corporate governance

22

committee, and may be considered at any point during the year. If any materials are provided by a stockholder in connection with the recommendation of a director candidate, such materials are forwarded to the nominating and corporate governance committee.

All proposals of stockholders that are intended to be presented by such stockholder at an annual meeting of stockholders must be in writing and notice must be delivered to the Corporate Secretary at our principal executive offices not later than the close of business on the 75th day, nor earlier than the close of business on the 105th day, prior to the first anniversary of the preceding year’s annual meeting. Stockholders are also advised to review our Bylaws, which contain additional requirements with respect to advance notice of stockholder proposals and director nominations.

23

Proposal No. 2: Ratification of Independent Registered Public Accounting Firm

Our audit committee has selected Ernst & Young LLP as our independent registered public accounting firm to perform the audit of our consolidated financial statements for the fiscal year ending December 31, 2025. Ernst & Young LLP audited our financial statements for the fiscal year ended December 31, 2024 and has been our independent registered public accounting firm since 2012. We expect that representatives of Ernst & Young LLP will join the Annual Meeting, will be able to make a statement if they so desire, and will be available to respond to appropriate questions.

At the Annual Meeting, the stockholders are being asked to ratify the appointment of Ernst & Young LLP as our independent registered public accounting firm for the fiscal year ending December 31, 2025. Our audit committee is submitting the selection of Ernst & Young LLP to our stockholders because we value our stockholders’ views on our independent registered public accounting firm and as a matter of good corporate governance. If this proposal does not receive the affirmative approval of a majority of the votes cast on the proposal, the audit committee would reconsider the appointment. Notwithstanding its selection and even if our stockholders ratify the selection, our audit committee, in its discretion, may appoint another independent registered public accounting firm at any time during the year if the audit committee believes that such a change would be in our best interests and those of our stockholders.

Principal Accountant Fees and Services

The following table presents fees for professional services for the fiscal years ended December 31, 2024 and 2023, for Ernst & Young LLP.

24

Audit Committee Pre-Approval of Audit and Permissible Non-Audit Services

Our audit committee generally pre-approves all audit and permissible non-audit services provided by our independent registered public accounting firm. These services may include audit services, audit-related services, tax services and other services. Pre-approval is detailed as to the particular service or category of services and is generally subject to a specific budget. Our independent registered public accounting firm and management are required to periodically report to the audit committee regarding the extent of services provided by our independent registered public accounting firm in accordance with this pre-approval, and the fees for the services performed to date. Our audit committee may also pre-approve particular services on a case-by-case basis. All of the services relating to the fees described in the table above were pre-approved by our audit committee.

25

Report of the Audit Committee

The information contained in the following report of the audit committee is not considered to be “soliciting material”, “filed” or incorporated by reference in any past or future filing by us under the Securities Exchange Act of 1934 or the Securities Act of 1933 unless and only to the extent that we specifically incorporate it by reference.

The audit committee of the Board of Directors of Trupanion, Inc. (the Company) has reviewed and discussed with the Company’s management and Ernst & Young LLP the Company’s audited consolidated financial statements as of and for the year ended December 31, 2024. The audit committee has also discussed with Ernst & Young LLP the matters required to be discussed by the applicable requirements of the Public Company Accounting Oversight Board (PCAOB) and the Securities and Exchange Commission.

The audit committee has received and reviewed the written disclosures and the letter from Ernst & Young LLP required by applicable requirements of the PCAOB regarding the independent accountant’s communications with the audit committee concerning independence, and has discussed with Ernst & Young LLP its independence.

Based on the review and discussions referred to above, the audit committee recommended to the Board of Directors that the audited consolidated financial statements be included in the Company’s Annual Report on Form 10-K for the year ended December 31, 2024 for filing with the Securities and Exchange Commission.

26

Executive Officers

The following sets forth information regarding our executive officers, including their respective ages and positions as of the record date. Biographical information pertaining to Ms. Tooth, who is both an executive officer and director of the Company, can be found in the Section titled “Our Board of Directors - Our Director Nominees.” There are no family relationships among any of our directors or executive officers.

Our Executive Officers

27

28

EMILY DREYER Senior Vice President, Channel Growth, Trupanion, Inc.   Age: 37
		Biography: Emily Dreyer has served as our Senior Vice President of Channels since June 2022. Prior to her current appointment, Ms. Dreyer served in various roles at Trupanion, including as our Vice President of Customer Marketing from January 2021 until June 2022, our Head of Customer Marketing from May 2017 to January 2021, our Senior Marketing Manager from September 2016 to May 2017, our Customer Acquisition Manager from September 2014 to September 2016, our Acquisition Specialist from January 2014 to September 2014, and as our Marketing Specialist from January 2013 to January 2014. Ms. Dreyer holds a B.A. from Trinity College.   Pet Memory: “I adopted my first dog, Dakota, when I was still in college and we became inseparable from that day forward. Our favorite thing to do together was go for a romp on the beach- rain, snow or shine. She would chase after seagulls, pull the legs off of crabs, and not listen to a word I said. Our walks together were a time for me to clear my head and we always returned tired and happy. She was diagnosed with cancer in 2016 and, thanks to Trupanion, we were able to have another year of walks on the beach together.” -Emily

29

Proposal No. 3: Advisory and Non-Binding Vote to Approve the Compensation Provided to the Company’s Named Executive Officers for 2024

Say-On-Pay

We are asking our stockholders to vote, on an advisory, non-binding basis, to approve a resolution on the compensation of the Company’s named executive officers, as reported in this proxy statement pursuant to Item 402 of Regulation S-K (commonly referred to as a “say-on-pay” vote). As described in the “Compensation Discussion and Analysis” section of this proxy statement, our compensation philosophy drives our compensation programs, which are designed to align the interests of our executive officers with those of our stockholders, our corporate objectives, our desired behaviors and company culture, as well as to attract, motivate, and retain key employees who are critical to the success of our Company. Under these programs, our executive officers, including our named executive officers, are motivated to achieve specific strategic objectives that are expected to increase stockholder value. Please read the “Compensation Discussion and Analysis” section of this proxy statement and the “Executive Compensation Tables” and narrative discussion for additional details about our compensation programs, including information about the 2024 compensation for our named executive officers.

Say-On-Pay Resolution

At the Annual Meeting, stockholders are being asked to approve the compensation of our named executive officers as described in this proxy statement by voting in favor of the resolution set forth below. This vote is not needed to address any specific item of compensation, but rather the overall compensation of our named executive officers and the policies and practices described in this proxy statement.

“RESOLVED, that the compensation paid to the Company’s named executive officers, as disclosed pursuant to the SEC’s executive compensation disclosure rules, including the Compensation Discussion and Analysis, compensation tables and narrative discussion, is hereby APPROVED.”

Even though this say-on-pay vote is advisory, and therefore will not be binding on us, we value the opinions of our stockholders. Accordingly, to the extent there is a significant vote against the compensation for our named executive officers, we will consider our stockholders’ concerns and the compensation committee will evaluate what actions may be necessary or appropriate to address those concerns. Stockholders who vote against the resolution are encouraged to contact the Board of Directors to explain their concerns in writing to:

Trupanion, Inc.

6100 4^th Avenue South, Suite 200

Seattle, Washington 98108

Attn: Corporate Secretary

30

Proposal No. 4: Advisory and Non-Binding Vote on the Frequency of Future Advisory Votes on the Compensation Provided to the Company’s Named Executive Officers

Say-On-Pay Frequency

We are asking our stockholders to vote, on an advisory, non-binding basis, on the frequency of future stockholder advisory votes on our executive compensation programs, such as Proposal No. 3. In particular, we are asking whether the advisory vote on compensation of our named executive officers should occur once every year, every two years, or every three years. After careful consideration of the frequency alternatives, our Board of Directors believes that conducting an annual advisory vote on the compensation of our named executive officers is appropriate for Trupanion and its stockholders at this time. The Board of Directors’ determination was influenced by the fact that the compensation of our named executive officers is evaluated, adjusted and approved on an annual basis. As part of the annual review process, our Board of Directors’ believes that the stockholder sentiment should be a factor that is taken into consideration by the Board of Directors and its compensation committee in making decisions with respect to the compensation of our named executive officers. By providing an advisory vote on the compensation for our named executive officers on an annual basis, our stockholders will be able to provide us with direct input on our compensation philosophy, policies and practices as disclosed in the proxy statement every year. We understand that our stockholders may have different views as to what the best approach for us, and we look forward to hearing from our stockholders on this agenda item each year. Accordingly, our Board of Directors recommends that the advisory vote on the compensation of our named executive officers be held every year.

Say-On-Pay Frequency Resolution

You may cast your vote for “1 YEAR”, “2 YEARS”, or “3 YEARS”, or you may “ABSTAIN” from voting in the response to the resolution set forth below:

“RESOLVED, that the option of once every year, two years, or three years that receives the highest number of votes cast for this resolution will be determined to the preferred frequency with which the Company is to hold an advisory and non-binding vote by stockholders to approve the compensation paid to the Company’s named executive officers, as disclosed pursuant to the SEC’s executive compensation disclosure rules, including the Compensation Discussion and Analysis, compensation tables and narrative discussion.”

The option of 1 year, 2 years or 3 years that receives the highest number of votes cast will be the frequency we select to hold future advisory votes on the compensation to our named executive officers. While as a corporate law matter approval requires a majority of the votes cast, we intend to honor the frequency selected by a plurality of the votes cast. Even though your vote is advisory and therefore will not be binding on us, we value our stockholders’ opinions and we intend to select the frequency receiving the most votes.

31

Executive Compensation

Compensation Discussion and Analysis

This Compensation Discussion and Analysis (CD&A) explains our executive compensation philosophy and programs, the decisions our compensation committee made under those programs, and the rationale for those decisions. In 2024 our named executive officers (NEOs) were:

Executive Summary

Company Performance and Alignment with Pay

2024 was a milestone year for Trupanion. Strong execution drove 20% subscription revenue growth, the doubling of our subscription margin in the fourth quarter from its quarterly low in 2023, and a record $39 million in free cash flow.

In 2024, we estimate that intrinsic value increased by approximately $879 million to $2.01 billion.

This strong performance was evidenced in incentive outcomes for the year:

32

2024 Compensation Program at a Glance

NEO target direct compensation is comprised of three core elements: a base salary, a short-term incentive program and an annual grant of equity-based long-term incentive (LTI) awards. The key features of our incentive plans and 2024 target direct compensation levels in effect for 2024 are summarized below.

Short-Term Incentives

Trupanion operated its legacy short-term incentive program design for the first six months of 2024 and implemented a new Management Incentive Plan (MIP) effective beginning in July 2024. Target opportunities were approved by the compensation committee and expressed as a percentage of salary. Payouts under both programs could range from 0% to 200% of target based on performance. Both designs incentivized and rewarded our performance in areas related to our financial, operational and strategic performance during the year.

Annual Long-Term Incentive Awards

Long-term incentive awards for 2024 performance were granted in February 2025 based on an assessment of intrinsic value per fully diluted share. We consider these grants part of 2024 compensation because they reflect our performance during the year. An aggregate pool is established with allocations to each NEO determined based on an assessment of individual performance. Awards are granted in the form of RSUs that will vest on a quarterly basis over two years, subject to continued service. Awards granted in February 2025, while considered part of 2024 compensation, will be reported in next year’s Summary Compensation Table.

Compensation Mix

The mix of our executive pay structure emphasizes incentive-driven, performance-based pay. This is designed to motivate our executives to achieve our long-term goals and deliver sustained increases in stockholder value without undue risk-taking. As described above, we evaluate compensation on a “performance year,” rather

33

than a “calendar year” basis. This means, for 2024 for example, we consider direct compensation to comprise salary earned in 2024, plus bonuses earned for 2024 performance, but paid in 2025, plus any long-term incentive award earned for 2024 performance and granted in 2025, promotion grants made in 2024, and new hire grants made in 2024. We currently do not target a specific compensation mix; rather, we monitor executive compensation mix to ensure that our compensation mix objectives of emphasizing long-term performance-based compensation, are being met.

The following pay mix charts reflect the mix of 2024 performance year compensation for our NEOs as described. We have excluded the compensation of our former CEO, Darryl Rawlings, from the CEO compensation mix table.

How Trupanion Manages Executive Pay

Key Operational and Governance Features of our Executive Compensation Framework

Trupanion is dedicated to maintaining an executive compensation program that effectively aligns pay with performance while embodying robust corporate governance standards. Below, we detail the core components of our approach.

34

Compensation Philosophy & Highlights:

Our compensation philosophy is mission-driven, aiming to attract, retain, and reward critical talent essential to our strategic objectives. By fostering a pay-for-performance culture, we ensure behavior aligns with performance metrics crucial to our business strategy. Our compensation structure is designed to incentivize performance in financial and operational areas that will contribute to intrinsic value per share growth, which is rewarded through our short- and long-term incentives. We recognize and encourage outstanding contributions at both the team and individual levels.

Say-on-Pay Vote Outcomes:

In 2024, we held a non-binding advisory say-on-pay vote at our Annual Meeting of Stockholders, where approximately 96.4% of shares voted were in favor of our proposal. The compensation committee viewed this strong approval as an endorsement of our executive compensation program. The committee will continue to consider the results of say-on-pay votes and stockholder feedback in making future compensation decisions.

Role of the Compensation Committee

The compensation committee is responsible for administering our executive compensation program, among other responsibilities, as provided in its charter. The Committee oversees the following items:

No NEO is present when their own compensation is being discussed. The full Board of Directors determines the compensation of the President & Chief Executive Officer. The compensation committee determines the compensation for the other executive officers, taking into consideration the recommendations from the President & Chief Executive Officer.

Role of Management

The compensation committee works closely with management to gather and analyze data to assist it with compensation decisions. In addition, our President & Chief Executive Officer reviews the performance of executive officers and provide recommendations regarding their compensation to the compensation committee for its consideration.

35

Additionally, our President & Chief Executive Officer and our Chief Administrative Officer annually support the compensation committee and the Board of Directors in its review of succession planning, given its critical importance to the Company’s success.

Role of Consultant

In 2024, the compensation committee engaged Meridian Compensation Partners, LLC (Meridian) as its independent compensation consultant. Meridian reported directly to the compensation committee and advised the committee on various executive pay issues.

In the fourth quarter of 2024 the committee conducted a review of its independent consultant and effective January 1, 2025 replaced Meridian with Willis Towers Watson (WTW) to provide advice on a go-forward basis. WTW will similarly report directly to the compensation committee.

Pursuant to SEC rules, the compensation committee assessed the independence of Meridian and WTW, concluding that both are independent and that neither had or have any conflict of interests with the Company, its directors or its executive officers.

Peer Group

The compensation committee identifies a comparator group of companies to evaluate the competitiveness of its compensation levels, policies, programs, and dilution. They also consult survey data for a broad evaluation of market pay levels for executive positions, using this information as a reference point rather than a determinant of pay levels.

Given the lack of direct public competitors in the pet insurance industry, comparator companies are identified based on similar business characteristics to Trupanion. Due to the changing nature of our business, in 2024 we updated the criteria to determine the peer group. This includes:

Based on these criteria, the committee identified comparator companies to inform compensation decisions, supplemented by broader market insights.

36

Executive Compensation for 2024

Base Salary

Base salary is intended to provide a market competitive level of fixed compensation that balances other performance-based elements of the pay mix. Salary levels are reviewed but not necessarily increased annually by the compensation committee and take into account an executive’s role and direct impact, and changes in market conditions based on our review of peer companies. Three NEOs received increases during 2024 in relation to their promotions and role expansions.

Short-Term Incentives

Short-term incentives are intended to focus our NEOs on the achievement of annual financial, operational and strategic goals that contribute to longer-term value creation for our stockholders.

For the first six months of 2024, our legacy short-term incentive design was in operation. Effective July 2024, the new MIP was approved. Target opportunities were approved by the compensation committee and expressed as a percentage of salary. Payouts under both programs could range from 0% to 200% of target based on performance.

Legacy Short-Term Incentive

Our legacy short-term incentive design was in effect for the first six months of the year. Performance was measured against monthly goals, with incentives earned based on this performance which the compensation committee assessed on a quarterly basis. An NEO became eligible to participate in the plan on the first day of the month following the NEO’s date of hire. Incentives were earned and paid based on performance relative to corporate goals, and additionally for select NEO’s individual goals. These individual goals were determined

37

by the President & Chief Executive Officer, and overseen by the compensation committee, and typically tied to initiatives indicative of growth, such as the number of active hospitals and enrolled pets.

Target opportunities are expressed as a percentage of salary. The compensation committee approved increases effective in May for all but one NEO to ensure opportunities remained market competitive.

Monthly corporate goals for 2024 were established in three areas: gross new pets under the age of three, cancellations, and subscription AOI. The table below highlights the definitions and significance of these metrics.

The compensation committee conducted reviews in April and July of the monthly achievement scores for the first two quarters. On average, the monthly achievement for the corporate objectives was 38%. This overall achievement was primarily driven by an average achievement of 25% for adjusted operating income and an average achievement of 17% for cancellations. For the first half of 2024, gross new pets under three saw an average monthly achievement of less than 1%.

38

In respect of the individual goals, the compensation committee considered the following:

(1) Mr. Kearns resigned as our Chief Legal Officer effective April 4, 2025.

While incentives were earned based on performance relative to monthly goals, any short-term incentives earned by the President & CEO, CFO, and former CEO were not paid until 2025 following the conclusion of our fiscal year. For all other NEOs awards were earned and paid monthly. Earned incentives were delivered in a combination of cash and fully-vested RSUs. NEOs had the choice to receive their earned value in fully-vested RSUs that were granted at a 20% premium and subject to a two-year lock-up period.

Based on the aforementioned targets, goals and payment policy, the compensation committee approved the following in respect of performance in the first six months of 2024.

Management Incentive Plan (MIP)

In July 2024, Trupanion implemented a new short-term incentive called the MIP. Target opportunities are expressed as a percentage of salary. The compensation committee approved increases effective in May for all but one NEO to ensure opportunities remained market competitive.

39

These changes are intended to increase the alignment of pay with our financial performance and simplify the incentive design for participants. Similar to legacy design, opportunities were established as a percentage of base salary as follows.