DEF 14A of Trupanion, Inc., Apr 30, 2025

DEF 14A of Trupanion, Inc.

Filed Apr 30, 2025 · FY20240001193125-25-107140

Open on EDGAR

  1. Proposal No. 1: Election of Directors

    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.

  2. Proposal No. 1: Election of Directors

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

  3. Our Board of Directors

    Our Board of Directors

  4. Board of Directors Snapshot

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

  5. Board of Directors Snapshot

    | Name | Age | | Max Brodén | 46 | | Jackie Davidson | 64 | | Paulette Dodson | 61 | | Richard Enthoven | 54 | | Murray Low | 72 | | Betsy McLaughlin | 64 | | Darryl Rawlings | 55 | | Howard Rubin | 72 | | Margi Tooth | 46 |

  6. Board of Directors Snapshot

    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.

  7. Our Directors and Nominees

    Our Directors and Nominees

  8. Our Directors and Nominees

    | MAX BRODÉN Executive Vice President and Chief Financial Officer of Aflac Incorporated Age: 46 | Director Since: 2023 | | | | Biography: | | | Max Brodén is the 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, managing an equity portfolio of global financial and insurance stocks. Max holds a Master of Science in both accounting and finance from Stockholm School of Economics. | | | Skills and Qualifications: | | “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 | 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 |

  9. Our Directors and Nominees

    | JACQUELINE “JACKIE” DAVIDSON Independent Business Consultant and Advisor Age: 64 | 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 11 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, is a Certified Public Accountant in the State of Washington and a Board Leadership Fellow of the National Association of Corporate Directors. | | | 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) |

  10. Our Directors and Nominees

    | PAULETTE DODSON Member of the Board of Directors For Bark, Inc., Portillo’s Inc., and Trupanion, Inc. Age: 61 | 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) |

  11. Our Directors and Nominees

    | RICHARD ENTHOVEN Director at PetSure Australia & Founder of Hollard Insurance Company Australia Age: 54 | 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 and currently serves as the Chairman of Greenstone and 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 |

  12. Our Directors and Nominees

    | MURRAY LOW Professor, Executive Education, Columbia Business School Age: 72 | 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 |

  13. Our Directors and Nominees

    | ELIZABETH “BETSY” MCLAUGHLIN Member of the Board Of Directors For Bark, Inc. and Trupanion, Inc. Age: 64 | Director Since: 2023 | | | Betsy is pictured above with her dogs, Max and Emma, both Labradoodles. “My dogs are happy Trupanion customers for life. Having just relocated to Park City, UT, both are 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 |

  14. Our Directors and Nominees

    | DARRYL RAWLINGS - Chair of the Board, Trupanion, Inc. Age: 55 | Director Since: 2000 | | | Darryl is pictured above with his dog, Priscilla, an English Bulldog. “Our beloved cat, Halle, passed away after 21 years. She was on my lap for 6 hours the day before she passed.”-Darryl | Biography: | | | Darryl is an established leader in medical insurance for cats and dogs. As founder, chair of the board, former CEO of Trupanion and founder and member of NAPHIA, Darryl is setting high standards for a growing industry, expanding public awareness of medical insurance for cats and dogs, and expanding the market across North America. Since founding Trupanion over 20 years ago, Darryl has been driven by a singular goal: to help the pets we love receive the best veterinary care. His passion for pet health runs deep. When he was 14, his family dog needed surgery that could have lengthened her life for another 12 years. The cost was beyond his parents’ means and they left the veterinary hospital without her. He vowed that someday pets would have even better medical insurance than people do. And Trupanion has fulfilled that promise with medical insurance for cats and dogs that is remarkably better than most human health insurance. Trupanion covered its first pet in Canada in 2000 and expanded to the United States in 2008. In July 2014, Darryl took this a step further, and lead the company through an IPO. Since then, Trupanion has established itself as a market leader and now provides medical insurance for cats and dogs in the United States, Canada, Europe, Puerto Rico and Australia. Under his leadership, the company experienced consistent growth, with annual revenues topping $1 billion. Trupanion now covers over 1,000,000 pets in its subscription business segment. Darryl is a graduate of the British Columbia Institute of Technology. His family includes his wife Caroline, two sons Sam and Bennett, and bulldogs Tristen and Priscilla. | | | 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 |

  15. Our Directors and Nominees

    | HOWARD RUBIN Director, Trupanion, Inc. Age: 72 | Director Since: 2010 | | | Howard is pictured above with his dog, Calvin, a Cavapoo. “Calvin is our sweet 10 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) |

  16. Our Directors and Nominees

    | MARGARET “MARGI” TOOTH Chief Executive Officer & President, Trupanion, Inc. Age: 46 | Director Since: 2024 | | | Margi is pictured above with her two dogs, Mabel, an English Bulldog, and Gertie, a Maltipoo. “Like many, my family introduced a pandemic puppy to the household over the last two years. Mabel, an English Bulldog joined us as a companion for our tiny Maltipoo, Gertie. Mabel is a bundle of fun and as rambunctious as any (bulldog!) puppy should be. Gertie, with her tiny stature and high-pitched yap have not, sadly, fallen in love with each other. Instead, Mabel has decided she is a sister to my three boys and follows them all around endlessly. The magic of what a pet can teach a child is evident in our household every day and I love seeing the bond grow between my two girls (dogs) and my three boys (humans).”-Margi | Biography: | | | Margi Tooth serves as our President and Chief Executive Officer. Margi is a 20-year pet insurance veteran and has been with Trupanion for over 12 years, she has been in the current position as CEO since taking over from founder, Darryl Rawlings. As Chief Executive Officer, Margi has a track record of driving Trupanion’s growth, having been at the helm of revenue delivery for the company since 2015. Ms. Tooth drives Trupanion’s strategic roadmap, spearheading initiatives to bring the transparent voice to the pet insurance world, expanding market presence and fostering a culture of excellence through execution. As Trupanion expands globally, British native, Margi is eager to share Trupanion’s veterinary-first approach across global markets while driving awareness in Trupanion’s home territories in Canada and the United States. Margi and her family reside in Seattle which include a Maltipoo and English Bulldog – both reminders of why Team Trupanion exists. | | | Skills and Qualifications: | | | Ms. Tooth serves as our Chief Executive Officer and President. | | | Board Committees: | | | None |

  17. Non-Employee Director Compensation

    Non-Employee Director Compensation

  18. Non-Employee Director Compensation Program

    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 31st, June 30th, September 30th, and December 31st, 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 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.

  19. 2024 Non-Employee Director Compensation Table

    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”.

  20. 2024 Non-Employee Director Compensation Table

    | Name | Fees Earned or Paid in Cash (1) | Stock Awards (2) | All Other Compensation | Total | | Max Brodén | $ — | $172,510 | $ — | $172,510 | | Jacqueline “Jackie” Davidson | $100,000 | $114,998 | $ — | $214,998 | | Paulette Dodson | $100,000 | $114,998 | $ — | $214,998 | | Richard Enthoven | $150,000 | $ — | $ — | $150,000 | | Dan Levitan (3) | $37,500 | $172,510 | $ — | $210,010 | | Murray Low (4) | $200,000 | $ — | $ — | $200,000 | | Elizabeth “Betsy” McLaughlin | $ — | $172,510 | $ — | $172,510 | | Darryl Rawlings (5) | $83,290 | $ — | $83,333 | $166,623 | | Howard Rubin (6) | $200,000 | $62,012 | $ — | $262,012 | | Zay Satchu (7) | $37,500 | $172,510 | $ — | $210,010 |

  21. 2024 Non-Employee Director Compensation Table

    | (1) Reflects applicable cash elections and prorations, as described above in “--Non-Employee Director Compensation Program.” |

  22. 2024 Non-Employee Director Compensation Table

    | (2) Reflects RSUs granted in 2024, net of cash elections and prorations, as described above in”--Non-Employee Director Compensation Program.” The amounts in this column represent the aggregate grant date fair value of the RSUs, as computed in accordance with Accounting Standards Codification Topic 718 (without regard to forfeitures). The amounts reflect accounting cost and may not correspond to the actual economic value realized by our directors. See Note 11 to our consolidated financial statements included in our Annual Report on Form 10-K for the year ended December 31, 2024 for a summary of the assumptions we apply in calculating these amounts. |

  23. 2024 Non-Employee Director Compensation Table

    | (3) Mr. Levitan received a grant of 6,326 RSUs in February 2024, representing 100% of his retainer. At the time Mr. Levitan’s service as a director terminated, 1,582 of such RSUs had vested and the remainder were returned to our 2014 Equity Incentive Plan pool. The dollar amount represented in the column entitled “Stock Awards” shows the aggregate grant date fair value of the 6,326 RSUs Mr. Levitan received, as computed in accordance with Accounting Standards Codification Topic 718 (without regard to forfeitures) as described in footnote 2. The aggregate grant date fair value of the 1,582 RSUs that vested, as computed in accordance with Accounting Standards Codification Topic 718 (without regard to forfeitures) as described in footnote 2, was $43,141. |

  24. 2024 Non-Employee Director Compensation Table

    | (4) As of December 31, 2024, Dr. Low held options to purchase 37,592 shares of common stock under certain option awards granted pursuant to our 2014 Equity Incentive Plan. |

  25. 2024 Non-Employee Director Compensation Table

    | (5) In 2024, following his resignation as an employee, we paid non-employee director Darryl Rawlings a prorated amount of his retainer for service as a director and chairperson of the board for the remainder of the year. We also paid Mr. Rawlings $83,333 in consideration for his services in connection with our pet food initiative, pursuant to a consulting agreement we entered into with Mr. Rawlings. |

  26. 2024 Non-Employee Director Compensation Table

    | (6) As part of his service to our Board of Directors, Mr. 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 Company, each wholly-owned subsidiaries of Trupanion. In consideration of his service as a director of each of these subsidiaries, we paid Mr. Rubin 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 $60,000 by our then-most current calculation of intrinsic value of a share of our common stock. |

  27. 2024 Non-Employee Director Compensation Table

    | (7) Dr. Satchu received a grant of 6,326 RSUs in February 2024, representing 100% of her retainer. At the time Dr. Satchu’s service as a director terminated, 1,582 of such RSUs had vested and the remainder were returned to our 2014 Equity Incentive Plan pool. The dollar amount represented in the column entitled “Stock Awards” shows the aggregate grant date fair value of the 6,326 RSUs Dr. Satchu received, as computed in accordance with Accounting Standards Codification Topic 718 (without regard to forfeitures) as described in footnote 2. The aggregate grant date fair value of the 1,582 RSUs that vested, as computed in accordance with Accounting Standards Codification Topic 718 (without regard to forfeitures) as described in footnote 2, was $43,141. |

  28. = “Committee Member”

    | • | evaluating, recommending, approving and reviewing executive officer and director compensation arrangements, plans, policies and programs; |

  29. Considerations in Evaluating Director Nominees

    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.

  30. Company Performance and Alignment with Pay

    | • | At December 31, 2024, the Company held $307.4 million in cash and short-term investments, including $35.4 million held outside the insurance entities, with an additional $15 million available under its credit facility. |

  31. Company Performance and Alignment with Pay

    | • | In aggregate, short-term incentive compensation in 2024 was awarded at a higher rate than in 2023, driven by a substantial increase in average corporate goal attainment scores in the second half of 2024. |

  32. Company Performance and Alignment with Pay

    | • | Based on strong intrinsic value growth during 2024 and consistent with our historical practice of granting performance RSUs when intrinsic value growth exceeds 10%, the equity allocation pool increased by 1.8 million shares. This pool was used to grant RSU awards to NEOs, among other purposes. |

  33. Short-Term Incentives

    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.

  34. Short-Term Incentives

    | Legacy Short-Term Incentive (January – June) | Management Incentive Plan (July – December) | | • Earned based on performance versus monthly goals which are reviewed on quarterly basis by the compensation committee • Ms. Tooth and Mr. Rawlings: 100% corporate goals • Other eligible NEOs: 50% corporate goals, 50% individual goals • Corporate metrics comprised Gross New Pets Added, Cancellations and Adjusted Operating Income • 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 • For Ms. Tooth and Messrs. Qureshi & Rawlings, any earned awards were paid or, in the case of RSUs, granted following year-end • For all other NEOs any earned awards were paid in cash on a monthly basis or issued in the form of RSUs on a quarterly basis | • Earned and paid based on performance versus annual goals (six months for 2024 given mid-year adoption) • All eligible NEOs: 100% corporate goals • Performance metrics comprise Adjusted Operating Income (AOI), Lifetime Value per Pet (LVP), and Internal Rate of Return (IRR) • NEOs had the choice to receive some or all of their earned MIP value in fully-vested RSUs that were granted at a 20% premium and subject to a two-year lock-up period |

  35. Annual Long-Term Incentive Awards

    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.

  36. Key Operational and Governance Features of our Executive Compensation Framework

    | ✓ | Deliver compensation primarily through performance-based incentives that encourage achieving both short- and long-term business goalsx | Do not allow automatic vesting of equity upon termination after a change in control or in other circumstances. | | ✓ | Cap payout opportunities at 200% of target to maintain reasonable compensation levels and discourage excessive risk-takingx | Avoid providing excessive benefits or perquisites, ensuring compensation remains aligned with our values | | ✓ | Engage with stakeholders through annual say-on-pay votes and regularly communicate with major stockholders to ensure transparencyx | Prohibit short sales and hedging and restrict pledging of company securities to uphold integrity and transparency | | ✓ | Employ an independent compensation consultant who advises the Compensation Committee for unbiased decision-makingx | Refrain from entering into individual employment agreements with predetermined terms unless legally required | | ✓ | Undertake an annual risk review of incentive programs | | | ✓ | Maintain robust share ownership guidelines such that our executives hold significant equity positions to align their interests with stockholders. | | | ✓ | Maintain compensation clawback policies that exceed SEC and NASDAQ requirements | |

  37. Role of the Compensation Committee

    | • | Executive officer salary adjustments, short-term incentive awards, equity awards, aggregate compensation, levels of individual performance, and form of equity awards; |

  38. Role of the Compensation Committee

    | • | Alignment of executive pay to performance, including salary and incentive awards; |

  39. Role of the Compensation Committee

    | • | Peer group and surveys used to gather market data; |

  40. Role of the Compensation Committee

    | • | Pay policies, such as severance, change in control severance, ownership guidelines, and clawbacks; |

  41. Role of the Compensation Committee

    | • | Director compensation; |

  42. Role of Consultant

    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.

  43. Peer Group

    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:

  44. Peer Group

    | • | Being publicly-traded and headquartered in the U.S.; |

  45. Peer Group

    | • | Categorized in tangential industries such as animal health and life and health insurance; |

  46. Peer Group

    | • | Revenue above $1 billion; |

  47. Peer Group

    | • | Similar business model characteristics such as recurring revenue, business-to-consumer transactions, and strategic relevance in the pet industry. |

  48. Peer Group

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

  49. Peer Group

    | Company | Ticker | Industry | | Central Garden & Pet Company | CENT | Animal Health | | Greenlight Capital | GLRE | Insurance | | Heritage Insurance Holding Inc. | HRTG | Insurance | | IDEXX Laboratories | IDXX | Animal Health | | Proassurance Corporation | PRA | Insurance | | Safety Insurance Group | SAFT | Insurance | | Skyward Specialty Insurance Group | SKWD | Insurance | | Stewart Information Services Corp | STC | Insurance | | Tiptree Inc. | TIPT | Insurance | | Universal Insurance Holdings | UVE | Insurance | | American Equity Investment Life | AEL | Insurance | | Elanco Animal Health | ELAN | Animal Health |

  50. Peer Group

    | Employers Holdings Inc. | EIG | Insurance | | Fidelis Insurance Holdings | FIHL | Animal Health | | Neogen Corporation | NEOG | Animal Health |

  51. Short-Term Incentives

    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.

  52. Legacy Short-Term Incentive

    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 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.

  53. Legacy Short-Term Incentive

    | Name | Period | Target Opportunity (% of Salary) | Target Opportunity (1) | Corporate Goals | Individual Goals | | Margi Tooth | Jan – April May – June | 40% 100% | $53,333 $66,666 | 100% | 0% | | Fawwad Qureshi | Jan – April | 40% | $40,000 | 50% | 50% | | | May – June | 75% | $50,000 | | | | John Gallagher | Jan – April | 40% | $40,000 | 50% | 50% | | | May – June | 50% | $25,000 | | | | Brenna McGibney (2) | Jan – April | 40% | $40,000 | 50% | 50% | | | May – June | 50% | $25,000 | | | | Darryl Rawlings | Jan – June | 40% | $60,000 | 100% | 0% | | Chris Kearns (3) | Jan – April | 40% | $30,000 | 50% | 50% | | | May – June | 50% | $25,000 | | |

  54. Legacy Short-Term Incentive

    | (1) Value reflects the opportunity for the six-months during which this design was in operation, and changes in NEO salaries and target opportunities as a percentage of salary. |

  55. Legacy Short-Term Incentive

    | (2) Ms. McGibney’s base salary is presented in USD. Ms. McGibney’s actual compensation is paid in CAD. We regularly review fluctuations in the USD/CAD exchange rate and make adjustments to the CAD payments with the objective of maintaining alignment with the intended USD base salary. |

  56. Legacy Short-Term Incentive

    | (3) Mr. Kearns resigned as our Chief Legal Officer effective April 4, 2025. |

  57. Legacy Short-Term Incentive

    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.

  58. Legacy Short-Term Incentive

    | Metric | Summary Definition (1) | Why it Matters | | Subscription Adjusted Operating Income (AOI) | This is the profit we make from an existing pet before we invest in acquiring new pets | Our adjusted operating income allows us to invest in acquiring new pets and other initiatives to support our growth. | | Gross New Pets Under Three | New Pets added for Trupanion under the age of three | Gross new enrollments for pets under three directly fuels future revenue growth and market share expansion. This figure is also an important driver for other key metrics like LVP and IRR. | | Cancellations | Number of cancelled pets for Trupanion | High cancellation volume negatively impacts growth along with other key metrics like LVP and IRR. |

  59. Legacy Short-Term Incentive

    | (1) We make adjustments to U.S. GAAP financial measures for purposes of this performance metric to ensure that results properly reflect management contributions. See Appendix A for an explanation of how this metric is calculated from our audited financial statements. |

  60. Legacy Short-Term Incentive

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

  61. Legacy Short-Term Incentive

    | Executive | Achievements relative to individual goals | Outcome (% of target) | | Fawwad Qureshi | Financial performance and reporting, strategic capital management, organizational effectiveness and technology optimization | 82% | | John Gallagher | Claims experience, enrollment growth, operational efficiency and compliance | 29% | | Brenna McGibney | Talent optimization and engagement, pricing strategy and operational effectiveness, organizational and leadership development | 65% | | Chris Kearns (1) | Enhancement of regulatory, compliance and privacy programs | 87% |

  62. Legacy Short-Term Incentive

    (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.

  63. Legacy Short-Term Incentive

    | Name | Total Target Opportunity | Total Earned Incentive (% of Target) | Total Earned Incentive (Cash Value) | Value Delivered in Cash | Valued Delivered in RSUs | Grant Date Fair Value of RSUs (1) | | Margi Tooth | $120,000 | 49% | $59,333 | $0 | $59,333 | $37,101 | | Fawwad Qureshi | $90,000 | 82% | $74,173 | $74,173 | $0 | $0 | | John Gallagher | $65,000 | 29% | $18,941 | $9,067 | $9,874 | $18,786 | | Brenna McGibney (2) | $65,000 | 65% | $42,235 | $14,344 | $27,892 | $24,438 | | Darryl Rawlings | $60,000 | 38% | $22,744 | $22,744 | $0 | $0 | | Chris Kearns (3) | $55,000 | 87% | $47,659 | $47,659 | $0 | $0 |

  64. Legacy Short-Term Incentive

    | (1) RSUs were granted to Ms. Tooth on February 27, 2025 and to Mr. Gallagher and Ms. McGibney on May 13, 2024. In determining the number of RSUs to be awarded, the value to be delivered in RSUs was increased by 20% and then divided by our then-current calculation of intrinsic value of a share of our common stock. The grant date fair market value of awards granted in February 2025 will be included in our 2025 Summary Compensation Table. The amounts represent aggregate grant date fair value of the RSUs, as computed in accordance with Accounting Standards Codification Topic 718 (without regard to forfeitures). The amounts reflect accounting cost and may not correspond to the actual economic value realized by our officers. See Note 11 to our consolidated financial statements included in our Annual Report on Form 10-K for the year ended December 31, 2024 for a summary of the assumptions we apply in calculating these amounts. |

  65. Legacy Short-Term Incentive

    | (2) Ms. McGibney’s base salary is presented in USD. Ms. McGibney’s actual compensation is paid in CAD. We regularly review fluctuations in the USD/CAD exchange rate and make adjustments to the CAD payments with the objective of maintaining alignment with the intended USD base salary. |

  66. Legacy Short-Term Incentive

    | (3) Mr. Kearns resigned as our Chief Legal Officer effective April 4, 2025. |

  67. Management Incentive Plan (MIP)

    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.

  68. Management Incentive Plan (MIP)

    | • | Performance is measured on a full-year basis, rather than monthly. Given the timing of the MIP’s adoption, for 2024 performance will be measured for the second six months of the year. For 2025, performance will be measured on a full-year basis. |

  69. Management Incentive Plan (MIP)

    | • | Individual performance has been removed, and incentives will be paid based solely on financial performance metrics. The financial metrics were also updated, as described below. |

  70. Management Incentive Plan (MIP)

    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.

  71. Management Incentive Plan (MIP)

    | Name | Period | Target Opportunity (% of Salary) | Target Opportunity (1) | | Margi Tooth | July – Dec | 100% | $262,500 | | Fawwad Qureshi | July – Dec | 75% | $150,000 | | John Gallagher (2) | July – Aug | 50% | $25,000 | | | Sept – Dec | 75% | $93,281 | | Brenna McGibney (3) | July – Dec | 50% | $75,000 | | Darryl Rawlings (4) | July | 40% | $10,000 | | Chris Kearns (5) | July – Dec | 50% | $75,000 |

  72. Management Incentive Plan (MIP)

    | (1) Value reflects the opportunity for the six-months during which this design was in operation, and changes in NEO salaries and target opportunities as a percentage of salary. |

  73. Management Incentive Plan (MIP)

    | (2) Mr. Gallagher’s target opportunity was increased in September in connection with his promotion to Chief Operating Officer. |

  74. Management Incentive Plan (MIP)

    | (3) Ms. McGibney’s base salary is presented in USD. Ms. McGibney’s actual compensation is paid in CAD. We regularly review fluctuations in the USD/CAD exchange rate and makes adjustments to the CAD payments with the objective of maintaining alignment with the intended USD base salary. |

  75. Management Incentive Plan (MIP)

    | (4) Mr. Rawlings did not transition from the legacy short-term incentive design to the new program. |

  76. Management Incentive Plan (MIP)

    | (5) Mr. Kearns resigned as our Chief Legal Officer effective April 4, 2025. |

  77. Management Incentive Plan (MIP)

    Although the MIP uses three different performance metrics, they fundamentally drive the same overall corporate objectives of in-year and future profitable growth as the legacy short-term incentive metrics. Those core corporate metrics included gross new pets under three, cancellation volume, and subscription adjusted operating income. The metrics below represent the results of these core drivers. Both gross new pets under three and cancellation volume directly impact lifetime pet value and internal rate of return. Growth in these core drivers is expected to increase subscription AOI, a major component of total adjusted operating income. Therefore, these top-level metrics reflect the overall performance driven by our core corporate focuses, which are essential for strong performance and a healthy growth trajectory.

  78. Management Incentive Plan (MIP)

    | Metric | Summary Definition (1) | Why it Matters | | Total Trupanion Adjusted Operating Income (AOI) | Adjusted operating income (non-GAAP) excludes acquisition costs, development expenses, nonrecurring items, and the gain/loss from a joint venture. Non-cash items like goodwill impairment, stock-based compensation, and depreciation/amortization are also excluded. | Reflects our performance in areas related to operating expense management, accurate pricing strategies, driving subscriber growth, retaining current subscriber and achieving operating efficiency goals | | Lifetime Value per Pet (LVP) | Lifetime value of a pet (including allocated fixed expenses) is calculated by taking subscription revenue less cost of subscription revenue (excluding related stock-based compensation, sign-up fees, and deferred revenue changes) over the past 36 months. This is further reduced by a pro-rata portion of general & administrative and technology expenses (less related stock-based compensation), all on a per-pet basis and multiplied by the implied average subscriber life in months. | Reflects our performance in areas related to ARPU, subscriber retention and profit per insured pet |

  79. Management Incentive Plan (MIP)

    | Internal Rate of Return (IRR) | This discount rate, assuming new pets mirror the average of the past 36 months, represents the rate at which the present value of a new pet’s projected lifetime cash flows equals its initial costs (acquisition and a 1% monthly capital charge on average new pet quarterly revenue). Future cash inflows are derived from the margin per pet applied to average new pet revenue for the period. | Reflects our performance in disciplined pet acquisition (PAC) spend, ARPU, subscriber retention and profit per insured pet |

  80. Management Incentive Plan (MIP)

    (1) Please see Appendix A for a description of our Key Performance Metrics. The compensation committee approved a 106% payout relative to target, driven by significant outperformance in LVP (200% achievement) and near-target performance in IRR (92% achievement). These positive results were partially offset by Trupanion AOI, which achieved 65% of its target. Based on the achievement and payment policy, the compensation committee approved the following in respect of performance in the second six months of 2024:

  81. Management Incentive Plan (MIP)

    | Name | Total Target Opportunity | Total Earned Incentive (% of Target) | Total Earned Incentive (Cash Value) | Value Delivered in Cash | Valued Delivered in RSUs | Grant Date Fair Value of RSUs (1) | | Margi Tooth | $262,500 | 106% | $277,618 | $0 | $277,618 | $210,696 | | Fawwad Qureshi | $150,000 | 106% | $158,640 | $158,640 | $0 | $0 | | John Gallagher | $118,281 | 106% | $124,760 | $124,760 | $0 | $0 | | Brenna McGibney (2) | $75,000 | 106% | $79,320 | $79,320 | $0 | $0 | | Darryl Rawlings (3) | $10,000 | 46% | $4,640 | $4,640 | $0 | $0 | | Chris Kearns (4) | $75,000 | 106% | $79,320 | $79,320 | $0 | $0 |

  82. Management Incentive Plan (MIP)

    | (1) RSUs were granted to Ms. Tooth on February 27, 2025 and to Mr. Gallagher on August 19, 2024. In determining the number of RSUs to be awarded, the value to be delivered in time-vested RSUs was increased by 20% and then divided by our then-current calculation of intrinsic value of a share of our common stock. The grant date fair market value of awards granted in February 2025 will be included in our 2025 Summary Compensation Table. The amounts represent aggregate grant date fair value of the RSUs, as computed in accordance with Accounting Standards Codification Topic 718 (without regard to forfeitures). The amounts reflect accounting cost and may not correspond to the actual economic value realized by our officers. See Note 11 to our consolidated financial statements included in our Annual Report on Form 10-K for the year ended December 31, 2024 for a summary of the assumptions we apply in calculating these amounts. |

  83. Management Incentive Plan (MIP)

    | (2) Ms. McGibney’s base salary is presented in USD. Ms. McGibney’s actual compensation is paid in CAD. We regularly review fluctuations in the USD/CAD exchange rate and makes adjustments to the CAD payments with the objective of maintaining alignment with the intended USD base salary. |

  84. Management Incentive Plan (MIP)

    | (3) Mr. Rawlings did not transition from the legacy short-term incentive design to the MIP. |

  85. Management Incentive Plan (MIP)

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

  86. Annual Long-Term Incentive Awards

    Annual Long-Term Incentive Awards Our annual long-term incentive program delivers equity-based awards to executives and other employees who contribute to the long-term success of the Company. The intent is to both reward for performance that contributed to value creation for our long-term stockholders and retain participants during the vesting period which generally requires continued service. Please see the above discussion regarding our Severance Policy and Change of Control Policy under the CD&A in the section titled “Severance and Change-in-Control Protection” for a discussion of equity acceleration. Awards are issued in the form of performance-based RSUs that can vest over two-years based on continued service. The value of the RSUs granted is informed by prior performance, based on estimates of the growth in our intrinsic value per share. The higher the growth of our intrinsic value per share, the larger the amount of equity we made available for grant in aggregate to executives and other employees. This pool is then allocated based on consideration of a number of factors, which, for our NEOs, includes their relative contribution to growth and other key financial metrics. Prior to June 2024, equity grants were made under our 2014 Equity Incentive Plan. Following its approval at our 2024 Annual Stockholder Meeting, awards are now made under our 2024 Equity Incentive Plan. For performance awards granted to our NEOs in 2025 for performance year 2024, the compensation committee, in consultation with management, evaluated the growth of our intrinsic value per share on a year-over-year basis. As in prior years, our compensation decisions are filtered through our model using inputs that are grounded by historical performance and analysis approved by the Board of Directors. As such, our intrinsic value growth per share in connection with compensation decisions is intended to be consistent with the following principles:

  87. Annual Long-Term Incentive Awards

    | • | Give credit for proven performance, generally based on historical three-year average trends, as well as the year-over-year growth rate of resulting intrinsic value per share changes, rather than performance we hope to achieve in the future. |

  88. Annual Long-Term Incentive Awards

    | • | Incorporate controllable factors, like advertising spending, but not give credit for or penalize participants for certain other factors that a participant is less likely to be able to influence, like changes in interest rates and foreign exchange rates, without compensation committee approval. |

  89. Annual Long-Term Incentive Awards

    | • | Allow for period-over-period comparisons not susceptible to manipulation by management. We generally base our inputs on the most recent three-year actual performance trend and prefer to avoid changing inputs such as the weighted average cost of capital when making compensation decisions. |

  90. Annual Long-Term Incentive Awards

    | • | Subject the calculation, including assumptions, to the scrutiny of the compensation committee, which may adjust the calculation and/or our awards if it determines that the equity pool and/or resulting grants are inappropriate or inconsistent with the long-term interests of stockholders. |

  91. Annual Long-Term Incentive Awards

    Ultimately, the compensation committee retains the discretion to modify the model by which we calculate intrinsic value per share, as it deems appropriate. If the growth in our intrinsic value per share is 10% or lower, we provide no long-term incentive awards to NEOs. For each increment of our calculated intrinsic value per share growth above 10%, the percentage of the incremental value is allocated between all employees and stockholders according to the following schedule:

  92. Annual Long-Term Incentive Awards

    | Estimated Increase to Our Calculation of Intrinsic Value Per Share | % of Value Creation Going to Stockholders (Assume RSUs) | % of Value Creation Going to Employees (Assume RSUs) | | 1 - 10% | 1 - 10% | 0.0% | | 11% | 10.7% | 0.3% | | 20% | 19.0% | 1.0% | | 30% | 27.5% | 2.5% | | 35% | 32.0% | 3.0% | | 40% | 36.5% | 3.5% | | 45% | 41.0% | 4.0% | | 50% | 45.5% | 4.5% | | 60% | 54.5% | 5.5% | | 70% | 63.5% | 6.5% |

  93. Annual Long-Term Incentive Awards

    (Progression between identified points is not linear due to the degree of difficulty in achieving greater increases to our calculation of intrinsic value per share. In the event our calculation of intrinsic value per share shows growth in excess of 70%, our compensation committee will determine the amount of equity we make available to grant in aggregate to all employees and non-employee directors.) Below is a depiction of how we reward intrinsic value per share growth using long-term incentive awards: Annual Equity Allocations for the 2024 Performance Year: For the 2024 performance year, we estimated a year-over-year growth of our intrinsic value per share at 74%. After adjustments for foreign exchange and cash usage, this resulted in an equity pool of 1.8M shares. Deductions were made for various grants as well as for repayment of historical grants for performance in prior years when the intrinsic value growth did not warrant equity dilution. This left 631,482 shares to be allocated as RSUs in 2025. Our President & Chief Executive Officer, with team input, assessed each NEO’s contribution to growth and leadership. The compensation committee reviewed these recommendations and approved the following long-term incentive grants to executive officers in February 2025 based on 2024 performance. These awards will be reported next year in our 2025 Summary Compensation Table.

  94. Annual Long-Term Incentive Awards

    | Name | Annual Performance- Based RSUs Granted in February 2025 | Grant Date Fair Value (1) | | Margi Tooth | 50,000 | $2,434,500 | | Fawwad Qureshi | 41,980 | $2,044,006 | | John Gallagher | 26,619 | $1,296,079 | | Brenna McGibney | 15,053 | $732,931 | | Darryl Rawlings | 0 | $0 | | Chris Kearns (2) | 5,369 | $261,417 |

  95. Annual Long-Term Incentive Awards

    | (1) The amounts represent aggregate grant date fair value of the RSUs, as computed in accordance with Accounting Standards Codification Topic 718 (without regard to forfeitures). The amounts reflect accounting cost and may not correspond to the actual economic value realized by our officers. See Note 11 to our consolidated financial statements included in our Annual Report on Form 10-K for the year ended December 31, 2024 for a summary of the assumptions we apply in calculating these amounts. |

  96. Annual Long-Term Incentive Awards

    | (2) Mr. Kearns resigned as our Chief Legal Officer effective April 4, 2025 and unvested RSUs were forfeited. |

  97. Off-Cycle Awards

    | Name | Rationale | Value(1) | | Key terms | | Margi Tooth | | Performance | $136,350 | Time-vested RSUs that vest as to 1/4th on the approximate one year anniversary of the date of grant and then 1/16th quarterly thereafter, subject to the named executive officer being a service provider through each vesting date. | | | | Promotion | $2,109,261 | | | Fawwad Qureshi | | Performance | $136,350 | | | John Gallagher | | Promotion | $542,726 | | | Brenna McGibney | | Performance | $545,400 | | | Darryl Rawlings | | Performance | $136,350 | | | Chris Kearns (2) | | New-hire | $1,395,542 | |

  98. Off-Cycle Awards

    | (1) The amounts represent aggregate grant date fair value of the RSUs, as computed in accordance with Accounting Standards Codification Topic 718 (without regard to forfeitures). The amounts reflect accounting cost and may not correspond to the actual economic value realized by our officers. See Note 11 to our consolidated financial statements included in our Annual Report on Form 10-K for the year ended December 31, 2024 for a summary of the assumptions we apply in calculating these amounts. |

  99. Off-Cycle Awards

    | (2) Mr. Kearns resigned as our Chief Legal Officer effective April 4, 2025 and unvested RSUs were forfeited. |

  100. Employment Agreements

    Employment Agreements No NEO has an employment agreement, although we did enter into an offer letter with Mr. Qureshi in connection with his appointment as our Chief Financial Officer. Pursuant to his offer letter, Mr. Qureshi is entitled to an annual base salary initially set at $300,000 and subject to adjustment, an annual bonus of up to 40% of his base salary (based 50% on corporate goals and 50% on individual goals), and participation in our Severance Plan (as defined below) with six months of salary and estimated COBRA premiums (less required tax withholding). Mr. Qureshi’s offer letter also entitled him to receive RSUs representing 60,000 shares of our common stock. This summary is not complete and is qualified in its entirety by reference to the full text and terms of the offer letter. Mr. Qureshi’s employment is at-will.

  101. Severance and Change-in-Control Protection

    Severance and Change-in-Control Protection Our Employee Severance and Change in Control Plan (our Severance Plan) provides certain severance benefits to eligible employees. Our Severance Plan is intended to standardize the severance paid to current and future employees. We believe our Severance Plan creates an equitable framework for situations when an employee leaves us involuntarily that applies equally to all team members regardless of title. Severance Policy: Under our Severance Plan, if an employee, including any NEO, is terminated without cause (defined to include willful or gross neglect of job duties, material breach of a fiduciary duty or Company policy, willful failure to comply with instructions from the Board or such person’s supervisor, continued unsatisfactory performance which has continued for more than thirty days following written notice, engagement in dishonest or illegal or gross misconduct, and conviction of a felony), then they are entitled to the following benefits:

  102. Severance and Change-in-Control Protection

    | • | a payment equal to the employee’s salary for a minimum of two weeks with an additional two weeks for each completed year of employment, up to a maximum of 26 weeks; |

  103. Severance and Change-in-Control Protection

    | • | for each full calendar quarter prior to the date of termination, any bonuses earned by the employee but unpaid as of the date of such termination; and |

  104. Severance and Change-in-Control Protection

    | • | a payment equal to one month of the medical insurance premium for the team member. |

  105. Severance and Change-in-Control Protection

    In order to receive these benefits, the employee must sign a separation agreement containing a full and unconditional release of claims. Change in Control Policy: If an employee, including any NEO, is terminated without cause in the three-month period before the occurrence of a Change in Control (the definition of “Change in Control” is set forth in footnote 5 to the “Termination of Employment and Change of Control Payments Table” below) or during the period of time beginning on the first occurrence of a Change in Control and lasting through the one-year anniversary of the occurrence of the Change in Control, then, in lieu of the severance payments set forth above, we will provide the employee with the following benefits:

  106. Severance and Change-in-Control Protection

    | • | six months of salary; |

  107. Severance and Change-in-Control Protection

    | • | for each full calendar quarter prior to the date of such termination, any bonuses earned by the employee but unpaid as of the date of such termination; and |

  108. Severance and Change-in-Control Protection

    | • | immediate vesting of all unvested equity awards. |

  109. Severance and Change-in-Control Protection

    In order to receive these benefits, the employee must sign a separation agreement containing a full and unconditional release of claims. If any total payment determined by this policy would result in an “excess parachute payment” (as defined in Section 280G of the Internal Revenue Code of 1986, as amended (Code)), then we would reduce the payment to produce a payment value that would maximize the “net after-tax amount” payable to the employee.

  110. Risk Assessment

    Risk Assessment Our compensation committee assessed the risk profile of our executive pay programs and determined that it does not encourage undue risk-taking by executives. Pay opportunities reflect a mix of fixed and at-risk compensation. At-risk compensation is tied to short- and long-term Company objectives and supports the pay-for-performance philosophy. The Company’s pay program emphasized the sustained viability of the business through the use of long-term incentive awards, especially for senior management. The long-term incentive awards are typically subject to an objective measurement (i.e., our calculation of intrinsic values per share) that assesses our long-term sustainable growth and health, and all of the long-term incentive awards carry four or two-year vesting, which encourages executives to make decisions that are in the best long-term interests of the business. Further, we require executives to hold meaningful levels of Company stock which results in stockholder alignment and a long-term focus. We also maintain a clawback policy, as more fully described below.

  111. Timing of Equity Awards

    Timing of Equity Awards We generally do not grant stock options (or similar awards) at times when there is MNPI about, or in the period beginning four business days before and ending one business day after we file a Form 10-K, 10-Q or with the SEC. We generally grant annual equity awards after the public release of the prior year’s financial results and grant, promotion, new hire or spot awards in the next open window period following the event. MNPI is not taken into account when determining the timing and terms of any equity award. Similarly, we do not time the disclosure of MNPI for the purpose of affecting the value of executive compensation.

  112. Summary Compensation Table

    Summary Compensation Table The following table provides information regarding all long-term incentive equity compensation earned by our named executive officers during the 2024, 2023 and 2022 fiscal years, and all short-term incentive compensation and salary earned by our named executive officers during the 2024, 2023 and 2022 fiscal years.

  113. Summary Compensation Table

    | Name and Principal Position | Year | Salary | Bonus | Stock Awards (1) | Non-Equity Incentive Plan Compensation (1) (2) (3) | All Other Compensation | Total | | Margi Tooth | 2024 | $462,500(4) | $2,245,611(5) | $1,363,500(6) | $336,951(7) | $ — | $4,408,563 | | Chief Executive Officer, President | 2023 | $358,333 | $ — | $579,400(8) | $26,861(9) | $ — | $964,594 | | | 2022 | $300,000 | $ — | $4,683,168 | $ —(10) | $ — | $4,983,168 | | Fawwad Qureshi | 2024 | $366,667(11) | $154,024(12) | $199,180(13) | $232,813 | $23,529(14) | $976,212 | | Chief Financial Officer | 2023 | $81,250(15) | $ — | $1,362,000(16) | $25,935 | $28,940(17) | $1,498,125 | | | 2022 | $ — | $ — | $ — | $ — | $ — | $ — | | John Gallagher | 2024 | $324,375(18) | $ — | $1,103,370(19) | $143,701(20) | $ — | $1,571,447 | | Chief Operating Officer | 2023 | $287,501(21) | $ — | $239,508(22) | $61,785(23) | $ — | $588,794 | | | 2022 | $ — | $ — | $ — | $ — | $ — | $ — | | Brenna McGibney | 2024 | $295,911(24) | $545,400(25) | $295,307(26) | $121,555(27) | $2,121(28) | $1,260,294 | | Chief Administrative Officer | 2023 | $ — | $ — | $ — | $ — | $ — | $ — | | | 2022 | $ — | $ — | $ — | $ — | $ — | $ — | | Darryl Rawlings | 2024 | $176,136(29) | $136,350(30) | $1,363,500(31) | $27,384 | $ — | $1,703,370 | | Former Chief Executive Officer | 2023 | $300,000 | $ — | $ — | $21,898(32) | $ — | $321,898 | | | 2022 | $300,000 | $ — | $1,356,281 | $ —(10) | $ — | $1,656,281 | | Chris Kearns | 2024 | $276,042(33) | $ — | $1,395,542(34) | $126,979 | $ — | $1,798,563 | | Former Chief Legal Officer | 2023 | $ — | $ — | $ — | $ — | $ — | $ — | | | 2022 | $ — | $ — | $ — | $ — | $ — | $ — |

  114. Summary Compensation Table

    | (1) If applicable, the amounts represent aggregate grant date fair value of the RSUs, as computed in accordance with Accounting Standards Codification Topic 718 (without regard to forfeitures). The amounts reflect accounting cost and may not correspond to the actual economic value realized by our officers. See Note 11 to our consolidated financial statements included in our Annual Report on Form 10-K for the year ended December 31, 2024 for a summary of the assumptions we apply in calculating these amounts. |

  115. Summary Compensation Table

    | (2) In lieu of taking their short-term incentive award in cash, team members may convert all or a portion of their short-term incentive award into Company equity, in the form of RSUs, with a 20% premium to cash on value and subject to a two year lock-up. |

  116. Summary Compensation Table

    | (3) For additional information regarding the non-equity incentive plan compensation, please refer to the CD&A, under the section titled “Detailed Description of Each Element of Compensation and Determination of Compensation for the 2024 Performance Year”. This column includes amounts earned for the prior fiscal year but paid the following fiscal year. |

  117. Summary Compensation Table

    | (4) Ms. Tooth’s salary was increased to $550,000 effective August 1, 2024 in connection with her appointment as CEO. |

  118. Summary Compensation Table

    | (5) Includes RSUs representing (i) 5,000 shares of the Company’s common stock issued in February 2024 as a spot bonus, which will vest over four years and (ii) 48,679 shares of the Company’s common stock issued in August 2024 as a spot bonus in connection with Ms. Tooth’s appointment as Chief Executive Officer, which will vest over four years. |

  119. Summary Compensation Table

    | (6) Reflects RSUs representing 50,000 shares of the Company’s common stock issued in February 2024 in connection with 2023 performance, which will vest over two years. |

  120. Summary Compensation Table

    | (7) For performance year 2024, Ms. Tooth earned a short-term incentive award in the amount of $336,951. Ms. Tooth converted 100% of her short-term incentive award into RSUs. Such RSUs were granted in February 2025 in the amount of 8,790 shares with an aggregate grant date fair value of $210,696. |

  121. Summary Compensation Table

    | (8) Reflects RSUs representing 20,000 shares of the Company’s common stock issued in August 2023 in connection with 2023 performance, which will vest over four years. |

  122. Summary Compensation Table

    | (9) For performance year 2023, Ms. Tooth earned a short-term incentive award in the amount of $21,674. Ms. Tooth converted 100% of her short-term incentive award into RSUs. Such RSUs were granted in February 2024 in the amount of 985 shares with an aggregate grant date fair value of $26,861. |

  123. Summary Compensation Table

    | (10) For the 2022 performance year, Mr. Rawlings and Ms. Tooth each waived receipt of their earned short-term incentive award, in the amounts of $21,534 and $21,534, respectively. |

  124. Summary Compensation Table

    | (11) Mr. Qureshi’s salary was increased to $400,000 effective May 1, 2024. |

  125. Summary Compensation Table

    | (12) Mr. Qureshi was granted RSUs representing 5,000 shares of the Company’s common stock in February 2024 as a spot bonus, which will vest over four years and a bonus in the amount of $17,674 in connection with additional responsibilities. |

  126. Summary Compensation Table

    | (13) Reflects RSUs representing 7,304 shares of the Company’s common stock issued in February 2024 in connection with prorated 2023 performance, which will vest over two years. |

  127. Summary Compensation Table

    | (14) Represents $20,704 in relocation expenses and $2,825 tax gross up for such expenses. |

  128. Summary Compensation Table

    | (15) Mr. Qureshi joined Trupanion as our Chief Financial Officer on September 25, 2023. Mr. Qureshi’s pro-rated salary for 2023 was $81,250. Mr. Qureshi became a named executive officer for the first time in 2023. |

  129. Summary Compensation Table

    | (16) Includes RSUs representing 60,000 shares of the Company’s common stock issued in November 2023 pursuant to Mr. Qureshi’s offer letter, which will vest over four years. |

  130. Summary Compensation Table

    | (17) Represents $17,457 in travel reimbursement and $11,483 tax gross up for such expenses. |

  131. Summary Compensation Table

    | (18) Mr. Gallagher’s base salary was increased to $375,000 effective September 4, 2024. |

  132. Summary Compensation Table

    | (19) Includes RSUs representing (i) 20,559 shares of the Company’s common stock issued in February 2024 in connection with 2024 performance, which will vest over two years and (ii) 13,838 shares of the Company’s common stock issued in November 2024 in connection with Mr. Gallagher’s appointment as Chief Operating Officer, which will vest over four years. |

  133. Summary Compensation Table

    | (20) For performance year 2024, Mr. Gallagher earned an aggregate short-term incentive award in the amount of $143,701. Mr. Gallagher converted a portion of his short-term incentive award into RSUs. Such RSUs were granted in (i) May 2024 in the amount of 636 shares with an aggregate grant date fair value of $14,100 and (ii) August 2024 in the amount of 152 shares with an aggregate grant date fair value of $4,686. |

  134. Summary Compensation Table

    | (21) Mr. Gallagher’s base salary from January 1, 2023 to February 1, 2023 was $230,000 and was increased to $260,000 on February 1, 2023 in connection with a promotion. Effective April 1, 2023 Mr. Gallagher’s salary was increased to $300,000 in connection with another promotion. Mr. Gallagher became a named executive officer for the first time in 2023. |

  135. Summary Compensation Table

    | (22) Includes RSUs representing (i) 7,223 shares of the Company’s common stock issued in August 2023 in connection with 2023 performance, which will vest over four years, (ii) 460 shares of the Company’s common stock issued in May 2023 as a promotion bonus, which will vest over four years, and (iii) 721 shares of the Company’s common stock issued in August 2023 as a promotion bonus, which will vest over four years. |

  136. Summary Compensation Table

    | (23) For performance year 2023, Mr. Gallagher earned a short-term incentive award in the amount of $60,754. Of that amount, Mr. Gallagher received cash in an aggregate amount of $13,332 and elected to convert the remainder of his short-term incentive awards into an aggregate of 2,207 RSUs with an aggregate grant date fair value of $48,453. |

  137. Summary Compensation Table

    | (24) Ms. McGibney was paid CAD $406,047. The table above reflects the USD equivalent using the exchange rate as of December 31, 2024. Ms. McGibney became a named executive officer for the first time in 2024. |

  138. Summary Compensation Table

    | (25) Ms. McGibney was granted RSUs representing 20,000 shares of the Company’s common stock in February 2024 as a spot bonus, which will vest over four years. |

  139. Summary Compensation Table

    | (26) Reflects RSUs representing 10,829 shares of the Company’s common stock issued in February 2024 in connection with 2023 performance, which will vest over two years. |

  140. Summary Compensation Table

    | (27) For performance year 2024, Ms. McGibney earned an aggregate short-term incentive award in the amount of $121,555. Ms. McGibney converted a portion of her short-term incentive award into RSUs. Such RSUs were granted in May 2024 in the amount of 989 shares with an aggregate grant date fair value of $24,438. Ms. McGibney was paid the remainder in CAD $139,484. The table above reflects the USD equivalent using the exchange rate as of December 31, 2024. |

  141. Summary Compensation Table

    | (28) Includes foreign exchange-related compensation true-up. |

  142. Summary Compensation Table

    | (29) Mr. Rawlings resigned as our CEO effective August 1, 2024. |

  143. Summary Compensation Table

    | (30) Mr. Rawlings was granted RSUs representing 5,000 shares of the Company’s common stock in February 2024 as a spot bonus, which will vest over four years. |

  144. Summary Compensation Table

    | (31) Reflects RSUs representing 50,000 shares of the Company’s common stock issued in February 2024 in connection with 2023 performance, which will vest over two years. |

  145. Summary Compensation Table

    | (32) For performance year 2023, Mr. Rawlings earned a short-term incentive award in the amount of $17,644. Of that amount, Mr. Rawlings converted 100% into RSUs. Such RSUs were granted in February 2024 in the amount of 803 shares with an aggregate grant date fair value of $21,898. |

  146. Summary Compensation Table

    | (33) Mr. Kearns was appointed Chief Legal Officer on January 31, 2024 and resigned effective April 4, 2025. |

  147. Summary Compensation Table

    | (34) Reflects RSUs representing 51,175 shares of the Company’s common stock issued in February 2024 pursuant to Mr. Kearns’ offer letter, which were to vest over four years. At the time of his resignation, one-fourth of such shares had vested. |

  148. Grants of Plan-Based Awards

    Grants of Plan-Based Awards The following table sets forth information regarding the short-term incentive awards earned by our named executive officers during fiscal year 2024, and the long-term incentive awards granted to our named executive officers in fiscal year 2024.

  149. Grants of Plan-Based Awards

    | | | | | Estimated Future Payouts Under Non-Equity Incentive Plan (1) | | | | | | Name | Award Type | Approval Date | Grant Date | Threshold | Target | Maximum | All Other Stock Awards: Number of Shares of Stock or Units | Grant Date Fair Value of Stock and Option Awards (2) | | Margi | Annual short-term incentive award (3) | | | $ — | $550,000 | $ — | | | | Tooth | RSU (4) | 2/27/2024 | 2/27/2024 | | | | 985 | $19,542 | | | RSU (5) | 2/26/2024 | 2/27/2024 | | | | 50,000 | $1,363,500 | | | RSU (6) | 2/26/2024 | 2/27/2024 | | | | 5,000 | $136,350 | | | RSU (7) | 7/23/2024 | 8/19/2024 | | | | 48,679 | $2,109,261 | | Fawwad | Annual short-term incentive award (3) | | | $ — | $300,000 | $ — | | | | Qureshi | RSU (5) | 2/26/2024 | 2/27/2024 | | | | 7,304 | $199,180 | | | RSU (6) | 2/26/2024 | 2/27/2024 | | | | 5,000 | $136,350 | | John | Annual short-term incentive award (3) | | | $ — | $281,250 | $ — | | | | Gallagher | RSU (4) | 2/27/2024 | 2/27/2024 | | | | 757 | $15,019 | | | RSU (5) | 2/26/2024 | 2/27/2024 | | | | 20,559 | $560,644 | | | RSU (4) | 5/13/2024 | 5/13/2024 | | | | 636 | $14,100 | | | RSU (4) | 8/19/2024 | 8/19/2024 | | | | 152 | $4,686 | | | RSU (7) | 10/22/2024 | 11/12/2024 | | | | 13,838 | $542,726 | | Brenna | Annual short-term incentive award (3) | | | $ — | $150,000 | $ — | | | | McGibney | RSU (4) | 2/27/2024 | 2/27/2024 | | | | 786 | $16,844 | | | RSU (5) | 2/26/2024 | 2/27/2024 | | | | 10,829 | $295,307 | | | RSU (6) | 2/26/2024 | 2/27/2024 | | | | 20,000 | $545,400 | | | RSU (4) | 5/13/2024 | 5/13/2024 | | | | 989 | $24,438 | | Darryl | Annual short-term incentive award (3) | | | $ — | $120,000 | $ — | | | | Rawlings | RSU (4) | 2/27/2024 | 2/27/2024 | | | | 803 | $15,932 | | | RSU (5) | 2/26/2024 | 2/27/2024 | | | | 50,000 | $1,363,500 | | | RSU (6) | 2/26/2024 | 2/27/2024 | | | | 5,000 | $136,350 | | Chris | Annual short-term incentive award (3) | | | $ — | $150,000 | $ — | | | | Kearns | RSU (8) | 2/29/2024 | 2/27/2024 | | | | 51,175 | $1,395,542 |

  150. Grants of Plan-Based Awards

    | (1) The amounts in these columns represent the threshold, target and maximum amounts of cash that might have become payable to each named executive officer as a short-term incentive award. Trupanion employees (including named executive officers) may elect to take their short-term awards in the form of equity with a 20% premium to cash on value but subject to a two-year lock-up. |

  151. Grants of Plan-Based Awards

    | (2) The amounts represent the aggregate grant date fair value of the RSUs, as computed in accordance with Accounting Standards Codification Topic 718 (without regard to forfeitures). The amounts reflect accounting cost and may not correspond to the actual economic value realized by our officers. See Note 11 to our consolidated financial statements included in our Annual Report on Form 10-K for the year ended December 31, 2024 for a summary of the assumptions we apply in calculating these amounts. |

  152. Grants of Plan-Based Awards

    | (3) These rows represent possible payouts pursuant to the annual short-term incentive awards. Trupanion employees (including named executive officers) may elect to take their short-term awards in the form of equity with a 20% premium to cash on value but subject to a two-year lock-up. |

  153. Grants of Plan-Based Awards

    | (4) Represents a portion of a short-term incentive award paid in the form of fully-vested RSUs with a 20% premium to the cash value, based on a volume-weighted average market price, and subject to a two-year lock-up. |

  154. Grants of Plan-Based Awards

    | (5) Reflects the long-term incentive awards received in the form of RSUs, which vests as to 1/8th of the award quarterly, subject to the recipient being a service provider through each vesting date. |

  155. Grants of Plan-Based Awards

    | (6) Reflects a spot bonus paid in RSUs, which vests as to 1/4th on the approximate one year anniversary of the date of grant and then 1/16th quarterly thereafter, subject to the recipient being a service provider through each vesting date. |

  156. Grants of Plan-Based Awards

    | (7) Reflects a promotion grant received in the form of RSUs, which vests as to 1/4th on the approximate one year anniversary of the date of grant and then 1/16th quarterly thereafter, subject to the named executive officer being a service provider through each vesting date. |

  157. Grants of Plan-Based Awards

    | (8) Reflects RSUs representing 51,175 shares of the Company’s common stock issued in February 2024 pursuant to Mr. Kearns’ offer letter, which were to vest over four years. At the time of his resignation on April 4, 2025, one-fourth of such shares had vested. |

  158. Outstanding Equity Awards at Fiscal Year-End

    Outstanding Equity Awards at Fiscal Year-End The following table provides information regarding stock options and RSUs held by our named executive officers as of December 31, 2024.

  159. Outstanding Equity Awards at Fiscal Year-End

    | | | Option Awards | | | | | Stock Awards | | | Name | Grant Date | Number of Securities Underlying Options Total Grant | Number of Securities Underlying Unexercised Options Exercisable | Number of Securities Underlying Unexercised Options Unexercisable | Option Exercise Price | Option Expiration Date | Number of Shares or Units of Stock That Have Not Vested | Market Value of Shares or Units of Stock That Have Not Vested (1) | | Margi Tooth | 8/19/2024(2) | | | | | | 48,679 | $2,346,328 | | | 2/27/2024(3) | | | | | | 5,000 | $241,000 | | | 2/27/2024(4) | | | | | | 31,250 | $1,506,250 | | | 8/14/2023(5) | | | | | | 13,750 | $662,750 | | | 2/28/2022(6) | | | | | | 16,328 | $787,010 | | | 2/22/2021(7) | | | | | | 2,927 | $141,081 | | | 5/4/2017(8) | 23,448 | 23,448 | — | $17.97 | 5/4/2027 | | | | | 12/21/2015(9) | 40,000 | 40,000 | — | $8.93 | 12/21/2025 | | | | | 7/24/2015(10) | 19,200 | 200 | — | $7.78 | 7/24/2025 | | | | Fawwad Qureshi | 2/27/2024(3) | | | | | | 5,000 | $241,000 | | | 2/27/2024(4) | | | | | | 4,565 | $220,033 | | | 11/13/2023(11) | | | | | | 45,000 | $2,169,000 | | John Gallagher | 11/12/2024(12) | | | | | | 13,838 | $666,992 | | | 2/27/2024(4) | | | | | | 12,850 | $619,370 | | | 8/14/2023(5) | | | | | | 4,966 | $239,361 | | | 8/14/2023(5) | | | | | | 495 | $23,859 | | | 5/15/2023(13) | | | | | | 288 | $13,882 | | | 2/28/2022(6) | | | | | | 3,673 | $177,039 | | | 2/22/2021(7) | | | | | | 816 | $39,331 | | | 2/22/2021(7) | | | | | | 19 | $916 | | Brenna McGibney | 2/27/2024(3) | | | | | | 20,000 | $964,000 | | | 2/27/2024(4) | | | | | | 6,769 | $326,266 | | | 8/14/2023(5) | | | | | | 3,719 | $179,256 | | | 8/14/2023(5) | | | | | | 298 | $14,364 | | | 5/15/2023(13) | | | | | | 173 | $8,339 | | | 2/27/2023(14) | | | | | | 279 | $13,448 | | | 8/12/2022(15) | | | | | | 1,636 | $78,855 | | Darryl Rawlings | 2/27/2024(3) | | | | | | 5,000 | $241,000 | | | 2/27/2024(4) | | | | | | 31,250 | $1,506,250 | | | 2/28/2022(6) | | | | | | 4,729 | $227,938 | | | 2/22/2021(7) | | | | | | 2,738 | $131,972 | | | 5/4/2017(8) | 23,448 | 3,448 | — | $17.97 | 5/4/2027 | | | | | 8/8/2016(16) | 50,000 | 2,000 | — | $14.95 | 8/8/2026 | | | | Chris Kearns | 2/27/2024(17) | | | | | | 51,175 | $2,466,635 |

  160. Outstanding Equity Awards at Fiscal Year-End

    | (1) Value is calculated by multiplying the number of RSUs or restricted stock awards that have not vested by the closing market price of our stock ($48.20) as of the close of trading on December 31, 2024 (the last trading day of the fiscal year). |

  161. Outstanding Equity Awards at Fiscal Year-End

    | (2) RSUs will vest as to 1/4th of the shares on August 22, 2025 and 1/16th vests each quarter thereafter. |

  162. Outstanding Equity Awards at Fiscal Year-End

    | (3) RSUs vested as to 1/4th of the shares on February 22, 2025 and 1/16th vests each quarter thereafter. |

  163. Outstanding Equity Awards at Fiscal Year-End

    | (4) RSUs vested as to 1/8th of the shares on May 22, 2024 and 1/8th vests each quarter thereafter. |

  164. Outstanding Equity Awards at Fiscal Year-End

    | (5) RSUs vested as to 1/4th of the shares on August 25, 2024 and 1/16th vests each quarter thereafter. |

  165. Outstanding Equity Awards at Fiscal Year-End

    | (6) RSUs vested as to 1/4th of the shares on February 25, 2023 and 1/16th vests each quarter thereafter. |

  166. Outstanding Equity Awards at Fiscal Year-End

    | (7) RSUs vested as to 1/4th of the shares on February 25, 2022 and 1/16th vests each quarter thereafter. |

  167. Outstanding Equity Awards at Fiscal Year-End

    | (8) Stock option vested as to 1/4th of the shares underlying this option on May 4, 2018 and 1/48th vested monthly thereafter. |

  168. Outstanding Equity Awards at Fiscal Year-End

    | (9) Stock option vested as to 1/4th of the shares underlying this option on January 7, 2017 and 1/48th vested monthly thereafter. |

  169. Outstanding Equity Awards at Fiscal Year-End

    | (10) Stock option vested as to 1/4th of the shares underlying this option on July 24, 2016 and 1/48th vested monthly thereafter. |

  170. Outstanding Equity Awards at Fiscal Year-End

    | (11) RSUs vested as to 1/4th of the shares on November 25, 2024 and 1/16th vests each quarter thereafter. |

  171. Outstanding Equity Awards at Fiscal Year-End

    | (12) RSUs will vest as to 1/4th of the shares on November 22, 2025 and 1/16th vests each quarter thereafter. |

  172. Outstanding Equity Awards at Fiscal Year-End

    | (13) RSUs vested as to 1/4th of the shares on May 25, 2024 and 1/16th vests each quarter thereafter. |

  173. Outstanding Equity Awards at Fiscal Year-End

    | (14) RSUs vested as to as to 1/4th of the shares on February 25, 2024 and 1/16th vests each quarter thereafter. |

  174. Outstanding Equity Awards at Fiscal Year-End

    | (15) RSUs vested as to as to 1/4th of the shares on August 25, 2023 and 1/16th vests each quarter thereafter. |

  175. Outstanding Equity Awards at Fiscal Year-End

    | (16) Stock option vested as to 1/4th of the shares underlying this option on August 8, 2017 and 1/48th vested monthly thereafter. |

  176. Outstanding Equity Awards at Fiscal Year-End

    | (17) RSUs vested as to 1/4th of the shares on February 22, 2025. Mr. Kearns resigned as our Chief Legal Officer effective April 4, 2025. |

  177. Option Exercises and Stock Vested Table

    Option Exercises and Stock Vested Table The following table provides information regarding stock options exercised, restricted stock and RSUs vested which were held by our named executive officers during fiscal year 2024.

  178. Option Exercises and Stock Vested Table

    | | | Option Awards | | Stock Awards | | | Name | Grant Date | Number of Shares Acquired on Exercise | Value Realized on Exercise | Number of Shares Acquired on Vesting | Value Realized on Vesting | | Margi Tooth | 4/3/2020 | | | 2,172 | $49,956 | | | 2/22/2021 | | | 11,707 | $444,992 | | | 2/28/2022 | | | 13,063 | $496,534 | | | 8/14/2023 | | | 6,250 | $299,975 | | | 2/27/2024 | | | 19,735 | $827,986 | | | 11/7/2014 | 7,500 | $299,590 | | | | Fawwad Qureshi | 11/13/2023 | | | 15,000 | $801,900 | | | 2/27/2024 | | | 2,739 | $117,028 | | John Gallagher | 4/3/2020 | | | 216 | $4,968 | | | 5/11/2020 | | | 49 | $1,276 | | | 2/22/2021 | | | 3,337 | $126,855 | | | 2/28/2022 | | | 2,938 | $111,667 | | | 5/15/2023 | | | 172 | $6,185 | | | 8/14/2023 | | | 2,483 | $119,170 | | | 2/27/2024 | | | 8,466 | $350,037 | | | 5/13/2024 | | | 636 | $19,570 | | | 8/19/2024 | | | 152 | $6,586 | | Brenna McGibney | 8/12/2022 | | | 934 | $35,495 | | | 2/27/2023 | | | 216 | $6,823 | | | 5/15/2023 | | | 104 | $3,728 | | | 8/14/2023 | | | 1,827 | $87,686 | | | 2/27/2024 | | | 4,846 | $194,907 | | | 5/13/2024 | | | 989 | $30,432 | | Darryl Rawlings | 4/3/2020 | | | 2,098 | $48,254 | | | 2/22/2021 | | | 10,951 | $416,257 | | | 2/28/2022 | | | 3,783 | $143,801 | | | 2/27/2024 | | | 19,553 | $823,023 |

  179. Pay Ratio

    Pay Ratio For fiscal year 2024:

  180. Pay Ratio

    | • | the annual total compensation, calculated as described below, of our Chief Executive Officer, Margi Tooth, was $4,776,913; and |

  181. Pay Ratio

    | • | the estimated median of the annual total compensation of all employees of our Company, other than Margi Tooth and Darryl Rawlings, who each served as our Chief Executive Officer in 2024, calculated as described below was $95,548. |

  182. Pay Ratio

    Both Mr. Rawlings and Ms. Tooth served as our Chief Executive Officer in 2024 and Ms. Tooth was serving in such role as of December 31, 2024, the date we used to determine the median employee. In order to determine the ratio of the annual total compensation of our Chief Executive Officer to the median of the annual compensation of all employees, we annualized Ms. Tooth’s base salary and non-equity incentive compensation as Chief Executive Officer and added the value of long-term incentive compensation granted to Ms. Tooth in 2024. We also included the value of RSUs granted to Ms. Tooth in 2024 but earned in 2023. Based on this information, for 2024 the ratio of the annual total compensation of our Chief Executive Officer to the median of the annual compensation of all employees was 50:1. To determine the median employee as of December 31, 2024, we used the total base earnings, bonuses earned, and the grant date fair value of equity granted in 2024 for all employees, full-time and part–time who were employed as of December 31, 2024 (excluding Mr. Rawlings and Ms. Tooth). We excluded independent contractors, as they are not employees. We also excluded fifteen employees located in Czechia, fourteen employees located in Germany, three employees located in Poland, three employees located in Belgium, and two employees located in Switzerland, who collectively, represent less than 5% of our workforce of 1,095 employees worldwide. The 2023 annual bonus (for certain executives) and the 2023 fourth quarter bonus for eligible employees were included as they were paid out in 2024. We did not include the 2024 annual bonus (for certain executives) nor the December 2024 bonus for eligible employees, as these were paid in 2025. For employees hired throughout the year, we annualized earnings based on amounts paid during the portion of 2024 in which they were employed. With the factors noted above, we identified the median role. We then annualized the total compensation set forth in the summary compensation table for Ms. Tooth, added to it the amounts we pay on behalf of Ms. Tooth pursuant to benefits programs that are available on a non-discriminatory basis to all our employees, including health, life and disability insurance premiums, child care at our headquarters, and enrollment of employee pets in our Trupanion medical insurance policy (Non-discriminatory Benefits) and compared that amount to the total compensation paid in 2024 for the identified role, which also included the Non-discriminatory Benefits paid out for the identified role. For the identified role and Ms. Tooth, we included the applicable 2023 bonus which was paid in 2024 but did not include the December 2024 bonus which was paid in 2025. This determined the ratio set forth above. In identifying the median employee under SEC rules, companies are permitted to use reasonable estimates, assumptions, and methodologies based on their own facts and circumstances. As a result, the disclosure regarding the compensation of our median employee may not be directly comparable to similar disclosure by other reporting companies.

  183. Pay Versus Performance

    Pay Versus Performance As required by Section 953(a) of the Dodd-Frank Wall Street Reform and Consumer Protection Act, and Item 402(v) of Regulation S-K, we are providing the following information about the relationship between “compensation actually paid” to Mr. Rawlings and Ms. Tooth, who each served as our Chief Executive Officer during 2024, and to our other named executive officers and certain company financial performance metrics. Compensation actually paid, as determined under SEC requirements, does not reflect the actual amount of compensation earned by or paid to our executive officers during a covered year. For further information concerning our compensation philosophy and how we align executive compensation with our performance, please refer to the Compensation Discussion and Analysis section of this proxy statement.

  184. Pay Versus Performance Table

    Pay Versus Performance Table

  185. Pay Versus Performance Table

    | | | | | | | | Value of Initial Fixed $100 Investment Based On: | | | | | Year (1) | SCT Total Compensation For CEO | | Compensation Actually Paid to CEO (2) | | Average SCT Total Compensation for Other NEOs | Average Compensation Actually Paid to Other NEOs (2) | Cumulative TSR | Peer Group Cumulative TSR (3) | Net Income | Company Selected Measure – Adjusted Operating Income (4) | | | Darryl Rawlings | Margi Tooth | Darryl Rawlings | Margi Tooth | | | | | | | | 2024 | $1,703,370 | $4,408,563 | $2,978,754 | $6,556,782 | $1,401,629 | $2,399,235 | $131.12 | $188.76 | $(9,633,000) | $114,468,000 | | 2023 | $321,898 | N/A | $(231,457) | N/A | $705,736 | $252,893 | $83.00 | $176.19 | $(44,693,000) | $83,545,000 | | 2022 | $1,656,281 | N/A | $(4,037,132) | N/A | $3,470,294 | $(1,316,756) | $129.30 | $105.70 | $(44,672,000) | $89,255,000 | | 2021 | $4,962,422 | N/A | $5,890,091 | N/A | $3,953,082 | $4,603,908 | $359.17 | $175.96 | $(35,530,000) | $78,454,000 | | 2020 | $1,160,767 | N/A | $6,273,363 | N/A | $1,249,292 | $6,331,960 | $325.65 | $138.58 | $(5,840,000) | $57,107,000 |

  186. Pay Versus Performance Table

    | (1) The CEO and other NEOs for the indicated years were as follows: (i) for 2024, our CEOs were Darryl Rawlings and Margi Tooth, and our other NEOs were Fawwad Qureshi, John Gallagher, Chris Kearns, and Brenna McGibney, (ii) for 2023, our CEO was Mr. Rawlings, and our other NEOs were Mr. Qureshi, Wei Li, Drew Wolff, Ms. Tooth, Mr. Gallagher, and Dr. Steve Weinrauch, (iii) for 2022, our CEO was Mr. Rawlings, and our other NEOs were Mr. Wolff, Ms. Tooth, Tricia Plouf, and Emily Dreyer, (iv) for 2021, our CEO was Mr. Rawlings, and our other NEOs were Mr. Wolff, Ms. Tooth, Ms. Plouf, and Gavin Friedman, and (v) for 2020, our CEO was Mr. Rawlings, and our other NEOs were Ms. Plouf, Ms. Tooth, Mr. Friedman, and Asher Bearman. |

  187. Pay Versus Performance Table

    | (2) Amounts reported in this column are based on total compensation reported for our CEO and other NEOs in the Summary Compensation Table for the indicated fiscal years and adjusted as shown in the table below. Fair value of equity awards was computed in accordance with our methodology used for financial reporting purposes. |

  188. Pay Versus Performance Table

    | Year | Executive(s) | Summary Compensation Table Total | Subtract Stock Awards | Add Year- End Equity Value (i) | Change in Value of Prior Equity Awards | Add Change in Value of Vested Equity Awards | Subtract Value of Equity Awards that Failed to Meet Vesting Conditions | Compensation Actually Paid | | 2024 | Mr. Rawlings | $1,703,370 | $(1,499,850) | $2,548,375 | $132,091 | $94,767 | $ — | $2,978,754 | | | Ms. Tooth | $4,408,563 | $(3,609,111) | $4,894,703 | $583,858 | $278,769 | $ — | $6,556,782 | | | Other NEOs | $1,401,629 | $(923,206) | $1,531,048 | $271,373 | $118,391 | $ — | $2,399,235 | | 2023 | CEO | $321,898 | $ — | $ — | $(268,695) | $(284,660) | $ — | $(231,457) | | | Other NEOs | $705,736 | $(418,688) | $605,318 | $(507,704) | $(131,770) | $ — | $252,893 | | 2022 | CEO | $1,656,281 | $(1,356,281) | $719,224 | $(3,095,658) | $(1,960,698) | $ — | $(4,037,131) | | | Other NEOs | $3,470,294 | $(3,169,003) | $1,680,494 | $(2,038,922) | $(1,259,619) | $ — | $(1,316,756) | | 2021 | CEO | $4,962,422 | $(4,623,067) | $5,788,691 | $340,352 | $(578,307) | $ — | $5,890,092 |

  189. Pay Versus Performance Table

    | | Other NEOs | $3,953,082 | $(3,635,556) | $4,529,917 | $376,093 | $(619,628) | $— | $4,603,908 | | 2020 | CEO | $1,160,767 | $(822,367) | $4,018,186 | $1,719,513 | $197,264 | $ — | $6,273,363 | | | Other NEOs | $1,249,292 | $(907,511) | $4,434,208 | $1,821,721 | $(265,751) | $ — | $6,331,960 |

  190. Pay Versus Performance Table

    | i. | With the exception of named executive officers, the Company issued short-term incentive awards (cash bonuses) to its team members on a monthly basis. In lieu of taking their full cash bonus amount, team members may elect to convert all or a portion of their cash bonus into equity, in the form of RSUs, with a 20% premium to cash on value, fully vested on grant date and subject to a two year lock-up. To avoid double counting, the average grant date fair value of RSUs granted pursuant to certain named executive officers electing to convert their cash bonus into RSUs is excluded from the column in this table for each covered fiscal year. |

  191. Pay Versus Performance Table

    | (3) The Company used the NASDAQ-100 Tech Peer Group Cumulative TSR for each covered fiscal year. |

  192. Pay Versus Performance Table

    | (4) In accordance with SEC rules, we are required to include in the Pay versus Performance table the “most important” financial measure (as determined by us) used to link compensation actually paid to our Chief Executive Officer and to our other named executive officers to our performance for the most recently completed fiscal year. We determined adjusted operating income, which is a measure included in our incentive program, meets this requirement and therefore, we have included this performance measure in the Pay versus Performance table. |

  193. Description of the Relationship Between Compensation Actually Paid to Our Named Executive Officers and Company Performance

    Description of the Relationship Between Compensation Actually Paid to Our Named Executive Officers and Company Performance The charts below describe the relationship between compensation actually paid to our Chief Executive Officers and to our other named executives officers (as calculated above) and our financial and stock performance for the indicated years. In addition, the first table below compares our cumulative TSR and peer group cumulative TSR for the indicated years.