trup-20260427

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

WASHINGTON, D.C. 20549

SCHEDULE 14A

(Rule 14a-101)

SCHEDULE 14A INFORMATION

Proxy Statement Pursuant to Section 14(a) of

the Securities Exchange Act of 1934

Filed by the Registrant þ

Filed by a Party other than the Registrant o

Check the appropriate box:

o Preliminary Proxy Statement

o Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2))

þ Definitive Proxy Statement

o Definitive Additional Materials

o Soliciting Material Pursuant to §240.14a-12

TRUPANION, INC.

(Name of Registrant as Specified In Its Charter)

Payment of Filing Fee (Check the appropriate box):

þ No fee required.

o Fee paid previously with preliminary materials.

o Fee computed on table below per Exchange Act Rules 14a-6(i)(1) and 0-11.

Trupanion Proxy Statement Title Page_DIGITAL.jpg

A LETTER TO OUR STOCKHOLDERS

April 27, 2026

Dear Trupanion Stockholders,

I am pleased to address you as the Chairperson of Trupanion and cordially invite you to attend the 2026 Annual Meeting of Stockholders (the Annual Meeting) of Trupanion, Inc. (the Company or Trupanion).

The Annual Meeting will be held on Wednesday, June 10, 2026 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 14, 2026 by following the instructions in this proxy statement, and bring the ticket with you to the meeting.

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 April 27, 2026, 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:

•access our proxy statement for the Annual Meeting and our Annual Report on Form 10-K for the fiscal year ended December 31, 2025, as filed with the SEC (the Annual Report);

•vote through the Internet, mail or by telephone; and

•receive paper copies of the proxy materials by mail, if desired.

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 14, 2026 by following the instructions in this proxy statement, and bring the ticket with you to the meeting.

Thank you for your continued support and trust in Trupanion.

Darryl Rawlings

Chairperson of the Board of Directors

Seattle, Washington

NOTICE OF ANNUAL MEETING OF STOCKHOLDERS

Notice of Annual Meeting of Stockholders

DATE:

June 10, 2026

TIME:

9:00 a.m. PDT

LOCATION:

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:

1.To elect nine directors to serve until the next annual meeting of stockholders and until a successor has been elected and qualified or until such director's earlier resignation or removal .

2.To ratify the appointment of Ernst & Young LLP as our independent registered public accounting firm for the fiscal year ending December 31, 2026.

3.To approve, on a non-binding advisory basis, the compensation provided to our named executive officers in 2025.

Record Date. Only stockholders of record at the close of business on April 14, 2026 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 Investor Relations by email at Investor.Relations@trupanion.com. If you are a registered holder, contact our transfer agent, Broadridge Corporate Issuer Solutions, Inc., by phone at (877) 830-4936 or by email at shareholder@broadridge.com or 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 14, 2026 by following the instructions in this proxy statement, and bring the ticket with you to the meeting.

By Order of the Board of Directors,

Asher Bearman

Chief Legal Officer

Seattle, Washington

April 27, 2026


IMPORTANT NOTICE REGARDING THE AVAILABILITY OF PROXY MATERIALS FOR THE ANNUAL MEETING OF STOCKHOLDERS TO BE HELD ON June 10, 2026. The Proxy Statement and our 2025 Annual Report on Form 10-K are available at https://investors.trupanion.com/financials/annual-reports/default.aspx and at https://www.proxyvote.com.

Table of Contents


Proxy Statement Summary			1
Information About Solicitation and Voting			1
Annual Meeting Agenda and Voting Recommendations			1

General Proxy Information			2
Record Date; Quorum			2
Internet Availability of Proxy Materials			2
Voting Rights; Required Vote			2
How Your Shares Are Voted			2
Voting Instructions; Voting of Proxies			3
Expenses of Soliciting Proxies			5
Revocability of Proxies			5
Electronic Access to the Proxy Materials			5
Voting Results			5

Proposal No. 1: Election of Directors			6

Our Board of Directors			7
Board of Directors Snapshot			7
Our Directors and Nominees			7

Non-Employee Director Compensation			14
Non-Employee Director Compensation Program			14
Additional Compensation for Non-Employee Directors			15
2025 Non-Employee Director Compensation Table			15

Corporate Governance			17
Corporate Governance Guidelines			17
Board Composition and Leadership Structure			17
Board's Role in Risk Oversight			17
Director Independence			18
Role of Lead Independent Director			18
Committees of Our Board of Directors			19
Corporate Governance and Ethics Principles			20
Insider Trading Policy			21
Compensation Committee Interlocks and Insider Participation			21
Board and Committee Meetings, Attendance, and Executive Sessions			22
Board Attendance at Annual Stockholders’ Meeting			22
Role of Stockholder Engagement			22


Communication with Directors			22
Considerations in Evaluating Director Nominees			22
Stockholder Recommendations for Nominations to the Board of Directors			23

Proposal No. 2: Ratification of Independent Registered Public Accounting Firm			24
Principal Accountant Fees and Services			24
Audit Committee Pre-Approval of Audit and Permissible Non-Audit Services			24

Report of the Audit Committee			25

Executive Officers			26
Our Executive Officers			26

Proposal No. 3: Approve, on a Non-Binding Advisory basis, the Compensation Paid to Our Named Executive Officers for 2025			30
Say-On-Pay			30
Say-On-Pay Resolution			30

Executive Compensation			31
Compensation Discussion and Analysis			31
Company Performance and Alignment with Pay			31
2025 Compensation Program at a Glance			31
Key Operational and Governance Features of our Executive Compensation Framework			33
Compensation Philosophy & Highlights			33
Say-on-Pay Vote Outcomes			34
Role of the Compensation Committee			34
Role of Consultant			34
Peer Group			35
Executive Compensation for 2025			36
2025 Performance Metrics			37
Adjusted Annual Operating Income (AOI)			37
Lifetime Value of Pets (LVP)			38
Internal Rate of Return (IRR)			38
2025 Payouts			38
Annual Long-Term Incentive Awards			39
Off-Cycle Awards			42
Other Compensation, General Benefits and Perquisites			42
Other Compensation Policies and Practices			42


Share Ownership			44
Risk Assessment			44
Clawbacks			44
Pledging & Hedging			45
Timing of Equity Awards			45

Compensation Committee Report			46

Executive Compensation Tables			47
Summary Compensation Table			47
Grants of Plan-Based Awards			49
Outstanding Equity Awards at Fiscal Year-End			50
Option Exercises and Stock Vested Table			51
Termination of Employment and Change of Control Payments Table			52
Narrative Discussion to Termination of Employment and Change of Control Payment Table			54

Pay Ratio			55

Pay Versus Performance			56
Pay Versus Performance Table			56
Description of the Relationship Between Compensation Actually Paid to Our Named Executive Officers and Company Performance			57
The Company's Most Important Financial Performance Measures			59

Equity Compensation Plan Information			60

Security Ownership of Certain Beneficial Owners and Management			61

Certain Relationships and Related Party Transactions			64
Consulting Arrangements			64
Review, Approval or Ratification of Transactions with Related Parties			64

Additional Information			65
Stockholder Proposals to be Presented at Next Annual Meeting			65
Delinquent Section 16(a) Reports			65
Available Information			66
“Householding” — Stockholders Sharing the Same Address			66

Information on Attending the 202 6 Annual Meeting of Stockholders			67

Appendix A			69

Table of Conten ts

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 2026 Annual Meeting to be held on Wednesday, June 10, 2026, 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 14, 2026 by following the instructions in this proxy statement, and bring the ticket with you to the meeting.

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



Proposal	Description	Board Recommendation

Proposal 1	Election of the nine director nominees named in this proxy statement	"FOR"
Proposal 2	Ratification and Appointment of Independent Registered Public Accounting Firm for the Fiscal Year Ending December 31, 2026	"FOR"
Proposal 3	Approval, on a non-binding advisory basis, the Compensation Provided to our Named Executive Officers for 2025	"FOR"

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General Proxy Information

Record Date; Quorum

Only holders of record of our common stock at the close of business on April 14, 2026, the record date, will be entitled to vote at the Annual Meeting. At the close of business on April 14, 2026, Trupanion had 43,620,472 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 April 27, 2026, 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, 2025. 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 14, 2026, 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 14, 2026, 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 14, 2026, 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 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.

Table of Conten ts

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 vote to approve the compensation provided to our named executive officers for 2025. 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 and 3 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 and 3. Accordingly, broker non-votes will have no effect on the election of directors or the advisory vote to approve compensation provided to our named executive officers for 2025.

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

Proposal

Recommended Vote

Vote Required

Impact of Withhold Votes/ Abstentions(1)

Broker

Non-Votes(2)

Proposal 1

Election of nine directors

"FOR"

Plurality(3)

No Effect

Proposal 2

Ratification and Appointment of Independent Registered Public Accounting Firm for the Fiscal Year Ending December 31, 2026

"FOR"

Majority of votes cast(4)

No Effect

Discretionary voting by broker permitted

Proposal 3

Advisory Vote to Approve the Compensation Provided to Our Named Executive Officers for 2025

"FOR"

Majority of votes cast(4)

No Effect

(1)Neither abstentions nor (in the case of Proposal 1) withhold votes will count as votes cast “FOR” or “AGAINST” any of the proposals, which means that abstentions and withhold votes will have no direct effect on the outcome of these proposals.

(2)Broker non-votes will have no direct effect on Proposals 1 and 3. Brokers are permitted to exercise their discretion and vote without specific instruction on Proposal 2.

(3)The directors will be elected by a plurality of the votes cast at the meeting. This means that 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” the nominees or “WITHHOLD” your vote with respect to one or more of the nominees.

(4)Approval of Proposals 2 and 3 will be obtained if the holders of a majority of the votes cast at the Annual Meeting vote “FOR” the proposal.

Voting Instructions; Voting of Proxies

If you are a stockholder of record, you may:

•vote through the Internet — in order to do so, please visit https://www.proxyvote.com and follow the instructions shown on your Notice of Internet Availability or proxy card;

•vote by telephone — in order to do so, please follow the instructions shown on your Notice of Internet Availability or proxy card;

•vote by mail — if you request or receive a paper proxy card and voting instructions by mail, simply complete, sign and date the proxy card and return it in the envelope provided; or

•vote in-person at the meeting — we will provide a ballot to stockholders who attend the meeting and wish to vote in-person. If you plan to attend the meeting, you must request an admission ticket by May 14, 2026 by following the instructions in this proxy statement, and bring the ticket with you to the meeting.

Table of Contents

Votes submitted through the Internet, by mail, or by telephone must be received by 11:59 p.m., Eastern Time, on June 9, 2026. 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.



To request an admission ticket to the Annual Meeting, please contact Investor Relations via e-mail at Investor.Relations@trupanion.com or by mail at Investor Relations, Trupanion, Inc., 6100 Fourth Avenue South, Suite 200, Seattle, Washington 98108 and send proof of stock ownership.

•If you are a registered stockholder, proof of your stock ownership is one of the following that shows your current name and address: the Proxy Card or the Notice of Internet Availability for the Annual Meeting.
•If you are a “proxy” for a registered stockholder, proof of stock ownership is (i) a valid, written “legal proxy” from the holder of record, naming you, signed by the registered stockholder and including the name and address of the registered holder of record, as recorded on their Notice of Internet Availability and (ii) either the Proxy Card or the Notice of Internet Availability (in the name of the registered stockholder).
•If you are a beneficial stockholder (that is, your shares are held in the name of a brokerage firm, bank or other nominee), proof of stock ownership is either the Voting Instruction Form or Notice of Internet Availability and a written “legal proxy”, naming you, signed by the brokerage firm, bank or other nominee that holds your shares. You should contact your brokerage firm, bank or other nominee to learn how to obtain a legal proxy.
•If you are a “proxy” for a beneficial stockholder, proof of stock ownership is (i) a valid, written “legal proxy” from the holder of record, naming you, signed by the beneficial stockholder’s brokerage firm, bank or other nominee and including the name and address of the beneficial holder of record, as recorded on the Notice of Internet Availability and (ii) either the Voting Instruction Form or the Notice of Internet Availability. You should contact your brokerage firm, bank or other nominee to learn how to obtain a legal proxy.
To allow time for processing, please submit requests for admission tickets by May 14, 2026. Admission tickets are not transferable. You may contact Investor Relations with any questions about the admission ticket process via e-mail at Investor.Relations@trupanion.com or by mail at Investor Relations, Trupanion, Inc., 6100 Fourth Avenue South, Suite 200, Seattle, Washington 98108.

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. 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 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 of this proxy statement, we do not know of any 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.

Table of Conten ts

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:

•delivering to the Corporate Secretary a written notice stating that the proxy is revoked;

•signing and delivering a proxy bearing a later date;

•voting again through the Internet or by telephone (by June 9, 2026, 11:59 p.m. Eastern Time); or

•attending and voting at the Annual Meeting (attendance at the meeting will not, by itself, revoke a proxy).

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:

•view our proxy materials for the meeting through the Internet;

•instruct us to mail paper copies of our future proxy materials to you; and

•instruct us to send our future proxy materials to you electronically by email.

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.

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Proposal No. 1: Election of Directors

As of the date of this Proxy Statement, our Board of Directors consists of ten directors, and immediately prior to the Annual Meeting the size of our Board of Directors will be automatically reduced to nine directors.

Mr. Max Brodén will not be standing for re-election at the Annual Meeting. Mr. Brodén's departure from the Board of Directors was for personal reasons and does not impact the strategic partnership between Aflac and Trupanion; Aflac remains committed to the partnership and continues to be a supportive, aligned shareholder. The Company thanks Mr. Brodén for his years of dedicated service and significant contributions to the Company.

Our nominating and corporate governance committee has nominated, Jacqueline "Jackie" Davidson, Paulette Dodson, Richard Enthoven, Murray Low, Elizabeth "Betsy" McLaughlin, Bradley "Brad" Powell, Darryl Rawlings, Howard Rubin, and Margaret “Margi” Tooth for election as directors at the 2026 Annual Meeting, and at the recommendation of our nominating and corporate governance committee, our Board of Directors proposes that Ms. Davidson, Ms. Dodson, Mr. Enthoven, Dr. Low, Ms. McLaughlin, Mr. Powell, Mr. Rawlings, Mr. Rubin, and Ms. Tooth each be elected as a director to serve until the next 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 directors 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 our officers, 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 nine directors.


OUR BOARD OF DIRECTORS RECOMMENDS A VOTE “FOR” ELECTION OF EACH OF THE NOMINATED DIRECTORS.

Table of Conten ts

Our Board of Directors

Board of Directors Snapshot

Our Board of Directors and their respective ages as of April 14, 2026 are as follows:


Name			Age
Max Brodén			47
Jackie Davidson			65
Paulette Dodson			62
Richard Enthoven			55
Murray Low			73
Betsy McLaughlin			65
Brad Powell			65
Darryl Rawlings			56
Howard Rubin			73
Margi Tooth			47

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


MAX BRODÉN Senior Executive Vice President and Chief Financial Officer of Aflac Incorporated Age: 47 \| Director Since: 2023
“I was told that Yorkies don’t swim……First time Bijou saw a pool he jumped in and wouldn’t get out for an hour and he hasn’t stopped since.” – Max			Biography:
			Max Brodén has served as a member of our Board of Directors since July 2023. Mr. Brodén is the Senior Executive Vice President and Chief Financial Officer of Aflac Incorporated where he has served in various leadership roles of ascending responsibility since April 2017. Before joining Aflac, he served as senior portfolio manager at Norges Bank from July 2007 to April 2017. Max holds a Master of Science in both accounting and finance from Stockholm School of Economics. Mr. Brodén's term as a director will end immediately prior to the Annual Meeting. We thank Mr. Brodén for his years of dedicated service and significant contributions to the Company.
			Skills and Qualifications:
			Mr. Brodén was chosen to serve on our Board of Directors based on his industry experience, finance and accounting knowledge, and strategic alignment.
			Board Committees:
			•Audit Committee

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JACQUELINE “JACKIE” DAVIDSON Independent Business Consultant and Advisor Age: 65 \| Director Since: 2018
Jackie is pictured above with her cats, Bear (left) and Sky (right), Tonkinese siblings. "We have had dogs and cats over the years and currently have two Tonkinese cats, Bear and Sky, siblings that are 14 years old. They are quite talkative, yet very calm and affectionate. Then there are the moments where play turns into sibling rivalry for a treat or toy, or the biggest prize, a place in our laps.” – Jackie			Biography:
			Jackie Davidson has served as a member of our Board of Directors since September 2018. Ms. Davidson is an independent business consultant and advisor. Previously, she served as the Chief Financial Officer of Market Leader, a SaaS software and lead generation service for real estate professionals from 2008 to 2014, and as Market Leader's Vice President of Finance from 2004 to 2008. She has held financial leadership positions at other public companies, including Penford Corporation and The Cobalt Group, and at other private companies. Ms. Davidson started her career at PricewaterhouseCoopers LLC. Ms. Davidson has served on private company and nonprofit boards, including the Washington CPA Foundation. Ms. Davidson holds a B.A. in Business Administration from Washington State University and is a Certified Public Accountant in the State of Washington. She is a Board Leadership Fellow of the National Association of Corporate Directors (NACD) and holds the NACD Director Certification.
			Skills and Qualifications:
			Ms. Davidson was chosen to serve on our Board of Directors based on her deep finance and accounting knowledge, expertise in recurring revenue businesses, and significant public company experience.
			Board Committees:
			•Audit Committee (Chair)


PAULETTE DODSON Member of the Board of Directors For Bark, Inc., Portillo’s Inc., and Trupanion, Inc. Age: 62 \| Director Since: 2023
Paulette is pictured above with Finley, a mixed breed dog. "My fondest memory of Teddy was his dedication to being the best office mate when I started to work from home due to the pandemic. He made sure I was at my work station on time and reminded me of when he thought it was high time for us to quit for the evening, not to mention the comfort he gave during those inevitably challenging days.” – Paulette			Biography:
			Paulette Dodson has served as a member of our Board of Directors since April 2023. Ms. Dodson has served as a member of the Board of Directors of Portillo's Inc., a public restaurant chain, since December 2021 and as a member of the Board of Directors for Bark, Inc., a public company that specializes in dog toys, treats and meal plans, since March 2023. Previously, she served as the General Counsel and Corporate Secretary at Alight Solutions LLC, an information technology and consulting public company, from May 2018 to August 2022. Prior to this, she was the Senior Vice President, General Counsel and Corporate Secretary at PetSmart Inc., a formerly public chain of pet superstores, from July 2012 to May 2018. Ms. Dodson holds a B.A. in Urban Legal Studies from City College of New York and a J.D. from Cornell Law School.
			Skills and Qualifications:
			Ms. Dodson was chosen to serve on our Board of Directors based on her extensive corporate governance experience and significant public company experience.
			Board Committees:
			•Nominating and Corporate Governance Committee (Chair)

Table of Conten ts


RICHARD ENTHOVEN Director at PetSure Australia & Founder of Hollard Insurance Company Australia Age: 55 \| Director Since: 2023
Richard is pictured with his dog. "Bailey, my Cavoodle, is my companion. Every day, while I work, she lies beneath my desk by my feet. If she senses that I might leave, she runs into the garage and waits by the car hoping to come with. I will never forget the joy and wellness she brought to our family during the lockdowns. Our kids would emerge from the home-schooling sessions, and she would run into their arms giving them love and joy!” – Richard			Biography:
			Richard Enthoven has served as a member of our Board of Directors since November 2023. Mr. Enthoven currently serves as the Chairman of Greenstone and as a Director of Hollard Holdings Australia and PetSure Australia. Mr. Enthoven is the founder, and former Chief Executive Officer (1999 to 2021) of The Hollard Insurance Company Pty Ltd and the co-founder of Greenstone Financial Services Ltd and PetSure Australia Pty Ltd. Mr. Enthoven also served as a Director of The Hollard Insurance Company and The Hollard Life Insurance Company in South Africa from 2004 to 2014, including Chairman of both companies from 2008 to 2014. Mr. Enthoven is also the Deputy President, and former President, of the Insurance Council of Australia. Mr. Enthoven holds a Master of Science from the London School of Economics and a Bachelor of Arts from the University of Southern California.
			Skills and Qualifications:
			Mr. Enthoven was chosen to serve on the Board based on his significant industry experience, track record growing global businesses, and strategic alignment.
			Board Committees:
			•Compensation Committee

Table of Contents


MURRAY LOW Professor, Executive Education, Columbia Business School Age: 73 \| Director Since: 2006
Murray is pictured above with his dog, Maggie, a toy poodle. “A few years ago I took a road trip around Cape Breton, Nova Scotia in my Airstream trailer with Maggie, my 12 year old, five-pound, toy poodle. We did lots of hiking, with Maggie leading the way. But then we came across a trail where dogs were not allowed. It was a moose pasture high on the hill above the wild Atlantic Ocean. So I stuffed Maggie in my backpack. Sure enough, after a short distance we came across a cow moose and a calf just a few feet off the trail. Maggie and I watched quietly, delighted to have shared the moment together." – Murray			Biography:
			Murray Low is currently the lead independent director on our Board of Directors and has served as a member of our Board of Directors since April 2006. Dr. Low previously served as the chairperson of our Board of Directors. In addition, Dr. Low served as our Secretary and Treasurer from April 2006 to June 2006. Dr. Low has been a professor at Columbia Business School since 1990 and was the Founding Director of the Eugene M. Lang Center for Entrepreneurship at Columbia Business School from July 2000 to September 2013. From September 2013 to July 2015, Dr. Low was the Director of Entrepreneurship Education at Columbia Business School. Since July 2015, Dr. Low has been Faculty of Executive Education at Columbia Business School. Since 1997, Dr. Low has also served as President of Low & Associates. Dr. Low holds a Ph.D. from the University of Pennsylvania, and an M.B.A. and a B.A. from Simon Fraser University.
			Skills and Qualifications:
			Dr. Low was chosen to serve on our Board of Directors due to his expertise in the areas of entrepreneurship and strategic management and his deep knowledge of our business.
			Board Committees:
			•Lead Independent Director •Nominating and Corporate Governance Committee

Table of Conten ts


ELIZABETH “BETSY” MCLAUGHLIN Member of the Board Of Directors For Bark, Inc. and Trupanion, Inc. Age: 65 \| Director Since: 2023
Betsy is pictured above with her dogs, Max and Emma, both Labradoodles. "My dog is a happy Trupanion customer for life. Living in Park City, UT, Max is thrilled with the mountain smells and landscape – sniffing, chasing squirrels and rolling endlessly in the snow!” – Betsy			Biography:
			Betsy McLaughlin has served as a member of our Board of Directors since April 2023. Ms. McLaughlin has served as a member of the Board of Directors for Bark Inc., a public company that specializes in dog toys, treats and meal plans, since December 2017. Previously, Ms. McLaughlin served in various leadership roles of ascending responsibility at Hot Topic, Inc., a public teen-oriented apparel and accessories chain, since joining the company in 1993, including serving as Chief Executive Officer and Director from 2000 to 2011. Ms. McLaughlin holds a B.A. in Economics from the University of California, Irvine.
			Skills and Qualifications:
			Ms. McLaughlin was chosen to serve on our Board of Directors based on her significant executive leadership experience and public company expertise.
			Board Committees:
			•Compensation Committee •Nominating and Corporate Governance Committee


Brad Powell Director, Trupanion, Inc. Age: 65 \| Director Since: 2025
Brad is pictured above with his cat, Ellie. "Cats and dogs have been a significant part of our family for most of my life. Our cat Ellie excels at interrupting zoom calls and walking across keyboards when she's not getting enough attention. She always brings a big smile to everyone's face." – Brad						Biography:
						Brad Powell has served as a member of our Board of Directors since October 2025. Mr. Powell served as Chief Financial Officer of Expeditors International of Washington, Inc., a publicly-traded global logistics company, from October 2008 to September 2025. Prior to joining Expeditors, Mr. Powell held several executive positions, including as President and Chief Financial officer of Eden Bioscience Corporation, a publicly-traded biotechnology company. Mr. Powell started his career at KPMG LLP and holds a B.S. in Accounting from Central Washington University.
						Skills and Qualifications:
						Mr. Powell was chosen to serve on the Board based on his accounting and financial acumen and his public company experience.
						Board Committees:
						•Audit Committee •Compensation Committee

Table of Contents


DARRYL RAWLINGS Chair of the Board, Trupanion, Inc. Age: 56 \| Director Since: 2000
Darryl is pictured above with his dog, Murray. "Murray got to see the airplane cockpit the first time he flew!” – Darryl						Biography:
						Darryl Rawlings has served as a member and Chairman of our Board of Directors since June 2006. Mr. Rawlings founded Trupanion in 1998 and served as our CEO from 1999 until his retirement in August 2024. In 2000, Trupanion issued its first policy to Mr. Rawlings' dog, Monty. Darryl is a graduate of the British Columbia Institute of Technology.
						Skills and Qualifications:
						Mr. Rawlings was chosen to serve on our Board of Directors based on his experience founding high-growth companies and his experience and familiarity with our business as its former Chief Executive Officer.
						Board Committees:
						•None


HOWARD RUBIN Director, Trupanion, Inc. Age: 73 \| Director Since: 2010
Howard is pictured above with his dog, Calvin, a Cavapoo. “Calvin is our sweet 13 year old Cavapoo who is eager to befriend all he meets. He has always joined us when visiting my 100 year old mother-in-law. During Covid’s lockdown periods, even when we were prohibited from visiting her, we made sure that Calvin visited regularly so no opportunity was missed to bring pure joy.” – Howard			Biography:
			Howard Rubin has served as a member of our Board of Directors since March 2010 and he was a consultant to Trupanion from May 2014 until December 2020. Mr. Rubin previously served as our Chief Operating Officer from March 2010 to May 2014, and as our Secretary from July 2012 to August 2013. Mr. Rubin founded and served as Chief Executive Officer at BrightHeart Veterinary Centers, a company operating specialty and emergency veterinary hospitals, from November 2007 to October 2009, and as the Chief Executive Officer of the National Commission on Veterinary Economic Issues, a non-profit association supporting the animal health and veterinary industry, from January 2001 to October 2007. Previously, he served as the Chief Executive Officer of Cardiopet, Inc., Divisional Vice President of IDEXX Laboratories, Inc., on the Board of Trustees of the Animal Medical Center in New York City, on the Dean’s Advisory Board for the College of Veterinary Medicine at Western University of Health Sciences and on the Board of Overseers of the Cummings School of Veterinary Medicine at Tufts University. Mr. Rubin also founded the Veterinary Referral Centre, a comprehensive, multi-specialty veterinary hospital. Mr. Rubin holds an M.B.A. from Washington University in St. Louis’ Olin Business School and a B.A. from Ohio Wesleyan University.
			Skills and Qualifications:
			Mr. Rubin was chosen to serve on our Board of Directors based on his extensive experience in the veterinary care and animal health industries.
			Board Committees:
			•Audit Committee •Compensation Committee (Chair)

Table of Conten ts


MARGARET “MARGI” TOOTH

SEC Form DEF 14A filed by Trupanion Inc.