DEF 14A of Tiptree Inc., Mar 16, 2026

DEF 14A of Tiptree Inc.

Filed Mar 16, 2026 · FY20250001393726-26-000015

Open on EDGAR

  1. Director Compensation

    Director Compensation The following table sets forth information regarding the compensation paid to, or earned by our directors, during fiscal 2025:

  2. Director Compensation Fiscal 2025

    Director Compensation Fiscal 2025

  3. Director Compensation Fiscal 2025

    | Name | Fees Earned or Paid in Cash ($) | Stock Awards ($)(1)(2) | Total ($) | | Michael G. Barnes(3) | — | — | — | | Paul M. Friedman | $120,000 | $144,824 | $264,824 | | Lesley Goldwasser | $125,000 | $144,824 | $269,824 | | Jonathan Ilany(3) | — | — | — | | Randy Maultsby(3) | — | — | — | | Dominique Mielle | $265,000 | $— | $265,000 | | Bradley E. Smith | $250,000 | $— | $250,000 |

  4. Director Compensation Fiscal 2025

    (1) The number of shares granted is based on the volume weighted average price for the ten trading days prior to the end of the quarter. The grant date closing market price of our common stock for each quarterly payment on each of April 3, 2025, July 3, 2025, October 3, 2025 and January 8, 2026 was $24.07, $23.95, $18.18, and $17.84, respectively. (2) Represents the grant date fair value of shares granted, as recognized by the Company for financial statement reporting purposes in the fiscal year ended December 31, 2025 in accordance with Accounting Standards Codification 718 — Compensation — Stock Compensation. See Note 10, Stock Based Compensation, to our consolidated financial statements in our 2025 Annual Report on Form 10-K. (3) Messrs. Barnes, Ilany and Maultsby receive no compensation in connection with their service on our Board. The compensation that they receive in their capacity as Executive Chairman, Chief Executive Officer (until December 31, 2025) and President, respectively, is included in the Summary Compensation Table below.

  5. Non-Employee Director Compensation Program

    Non-Employee Director Compensation Program In fiscal 2025, each non-employee director was eligible to receive an annual cash retainer of $137,500 plus $112,500 in immediately vested shares of our common stock, both of which are paid quarterly in arrears. Non-employee directors may elect to receive up to $150,000 of total compensation in the form of immediately vested common stock and the cash compensation payable to such director would be reduced proportionately. Individual non-employee Directors who own, directly or indirectly, at least 50,000 shares of common stock at the time of his or her election, may elect to receive some or all of the common stock portion in cash instead and the stock compensation would be reduced proportionately. The Lead Director received an additional annual retainer of $25,000, the Chair of the Audit Committee received an additional annual retainer of $20,000 and the Chair of the CNG Committee received an additional annual retainer of $15,000. In addition, we reimburse all directors for reasonable out-of-pocket expenses incurred in connection with their services on our Board of Directors.

  6. CONTINUING DIRECTORS

    CONTINUING DIRECTORS The following table and biographical descriptions set forth certain information, as of March 16, 2026, with respect to each continuing director.

  7. CONTINUING DIRECTORS

    | Name | Age | Director Since | | Class II | | | | Michael G. Barnes | 59 | August 2010 | | Dominique Mielle (Chair of the CNG Committee) | 57 | January 2020 | | Class III | | | | Lesley Goldwasser (Lead Independent Director) | 64 | January 2015 | | Jonathan Ilany | 72 | August 2010 |

  8. CONTINUING DIRECTORS

    Michael G. Barnes has been a member of our Board of Directors since August 2010, and he currently serves as the Chairman of our Board of Directors. On January 1, 2026, he was also appointed as our Chief Executive Officer. In 2007 Mr. Barnes founded Tiptree Financial Partners, L.P. (“TFP”) and served as Chief Executive Officer until 2012 and Chairman until its merger with Tiptree in 2018. In addition, Mr. Barnes is a founding partner and principal of Tiptree Advisors Holdings, L.P., formerly known as Corvid Peak Holdings, L.P., and its affiliated companies. Prior to the formation of Tiptree Advisors in 2003, Mr. Barnes spent two years as Head of Structured Credit Arbitrage within UBS Principal Finance LLC, a wholly owned subsidiary of UBS Warburg LLC (“UBS”) that conducted proprietary trading on behalf of the firm. Mr. Barnes joined UBS in 2000 as part of the merger between UBS and PaineWebber Inc. Prior to joining UBS, Mr. Barnes was a Managing Director and Global Head of the Structured Credit Products Group of PaineWebber. Prior to joining PaineWebber in 1999, he spent 12 years at Bear Stearns, the last five of which he was head of their Structured Transactions Group. Mr. Barnes was the Chairman of the Board of Philadelphia Financial Group, Inc., a private placement life insurance, annuity and administration company, from June 2010 until June 2015 and Care Investment Trust Inc., a senior living real estate company, from August 2010 until February 2018. Mr. Barnes received his A.B. from Columbia College. Mr. Barnes was selected and qualified to serve as a member of our Board of Directors because of his extensive senior level experience in the investment management industry and his extensive knowledge of our business and industries. Dominique Mielle has been a member of our Board of Directors since January 2020 and was appointed as the Chairperson of the CNG Committee in August 2020. Ms. Mielle was a partner and senior portfolio manager at Canyon Partners (“Canyon”) from 1998 to 2017, focusing on the transportation, technology, retail and consumer products sectors, corporate and municipal bond securitizations and leading Canyon’s collateralized loan obligations business. She was named one of the “Top 50 Women in Hedge Funds” by Ernst & Young in 2017. Prior to joining Canyon in 1998, Ms. Mielle worked at Libra Investment Services, Lehman Brothers Inc. and Credit Lyonnais. She was a director of Anworth Mortgage Asset Corporation, a mortgage REIT investment firm where she was the chair of the compensation committee and a member of the audit committee from 2018 until its merger with Ready Capital Corp. in 2021. In connection with the merger, Ms. Mielle became a director of Ready Capital Corp., where she is the chair of the audit committee and serves on the compensation committee. She is also a director of Studio City International since 2018, where she is the chair of the nominating and corporate governance committee and serves on the compensation and audit and risk committees. Ms. Mielle was formerly a director of PG&E Corporation and Pacific Gas and Electric Company from April 2019 until June 2020, where she was the chair of the audit committee, and formerly a director of Osiris Acquisition Corp. from 2021 until May 2024, where she was the chair of the audit committee. She was also formerly a director of Digicel Group from July 2020 to February 2023. Ms. Mielle is the author of Damsel in Distressed and is a contributing author to Security Analysis, 7th Edition by Graham and Dodd. Ms. Mielle graduated with an M.B.A. in Finance from Stanford University and a Master in Management degree from Ecole des Hautes Etudes Commerciales in France (HEC Paris). Ms. Mielle was selected and qualified to serve as a member of our Board of Directors because of her extensive financial services industry experience on Wall Street, investing in fixed income and leading capital structure optimizations and restructurings. Lesley Goldwasser has been a member of our Board of Directors since January 2015. Ms. Goldwasser has been a Managing Partner of GreensLedge Capital Markets LLC (“GreensLedge”) since September 2013. Prior to joining GreensLedge, Ms. Goldwasser was associated with Credit Suisse Group AG (“Credit Suisse”) as a Managing Director from September 2010 to November 2013, where she had global responsibility for the Hedge Fund Strategic Services unit. Before Credit Suisse, Ms. Goldwasser spent 12 years at Bear Stearns where she was co-head of Global Debt and Equity Capital Markets units and had global responsibility for structured products. Prior to her tenure at Bear Stearns, Ms. Goldwasser spent 12 years at Credit Suisse in a variety of management positions, including responsibility for both the Asset Backed and Non-Agency Mortgage Trading Desks. She is on the Board of Directors of Liquid Telecom and joined the board of Fold, Inc. in February 2025 and is a member of its audit committee. Ms. Goldwasser also joined the Board of Directors of Caledonia Mining Corporation plc in February 2025 and is a member of its audit and compensation committees. Ms. Goldwasser also joined the board of Figure Technology Solutions, Inc. in September 2025 and is a member of its audit committee. She previously served on the board of FinTech Acquisition Corp. V from December 2020 through its liquidation in December 2022. She was also a director of FTAC Parnassus Acquisition Corp. from March 2021 until its liquidation in March 2023. Ms. Goldwasser is a graduate of the University of Cape Town, South Africa. Ms. Goldwasser was selected and qualified to serve as a member of our Board of Directors because of her diverse and extensive business and financial experience across a variety of investment banking disciplines. Jonathan Ilany has been a member of our Board of Directors since August 2010. He was our Chief Executive Officer until December 31, 2025, and effective January 1, 2026, he was appointed our Vice Chairman of our Board of Directors and is an advisor to Tiptree. From February 2015 to November 2015, Mr. Ilany was our Co-Chief Executive Officer. From October 2014 until February 2015, he was our Executive Vice President, Head of Mortgage Finance and Asset Management. Mr. Ilany served as a director of Rescap, a subsidiary of Ally Bank, from November 2011 until December 2013. Mr. Ilany also served as a director of Care Investment Trust Inc., a senior living real estate company from August 2010 until February 2018. Mr. Ilany was a partner at Mariner Investment Group from 2000 until 2005, responsible for hiring and setting up new trading groups, overseeing risk management and serving as a senior member of the Investment Committee and Management Committee. From 1994 until 2000, Mr. Ilany was a private investor. From 1982 until 1994, Mr. Ilany held various senior management roles at Bear Stearns, including as a Senior Managing Director and a member of the board of directors. From 1980 until 1982, Mr. Ilany worked at Merrill Lynch. From 1971 until 1975, Mr. Ilany served in the armored corps of the Israeli Defense Forces, and he was honorably discharged holding the rank of First Lieutenant. Mr. Ilany received his B.A. and M.B.A. from the University of San Francisco. Mr. Ilany was selected and qualified to serve as a member of our Board of Directors because of his extensive risk management and senior managerial experience in the financial services industry, his board experience, his experience with investing in real estate and real estate-related assets and his extensive knowledge of our business and industries.

  9. PROPOSAL 1: ELECTION OF DIRECTORS

    PROPOSAL 1: ELECTION OF DIRECTORS Our Board of Directors is classified into three classes: Class I, consisting of Paul M. Friedman, Randy Maultsby and Bradley E. Smith, to hold office for a term expiring at this Annual Meeting of stockholders; Class II, consisting of Michael G. Barnes and Dominique Mielle, to hold office for a term expiring at the 2027 annual meeting; and Class III, consisting of Jonathan Ilany and Lesley Goldwasser, to hold office for a term expiring at the 2028 annual meeting. Our Fifth Amended and Restated Bylaws (“Bylaws”) provide that a majority of the entire Board of Directors may establish, increase or decrease the number of directors, provided that the number of directors shall never be less than one (1), which is the minimum number required by the Maryland General Corporation Law, nor more than fifteen (15).

  10. Information Regarding the Nominees for Election

    Information Regarding the Nominees for Election The following table and biographical descriptions set forth certain information, as of March 16, 2026, with respect to each nominee for election as director at the Annual Meeting. Messrs. Friedman, Maultsby and Smith each currently serve as a director. All nominees for director have consented to be named and have agreed to serve as directors if elected. We have no reason to believe that any of the nominees will be unable to accept election as a director. However, in the event that one or more nominees are unable or unwilling to accept election or are unable to serve for any reason, the persons named as proxies or their substitutes will have authority, according to their judgment, to vote or refrain from voting for such substitute as may be designated by the Board of Directors.

  11. Information Regarding the Nominees for Election

    | Nominees for Election as Class I Directors | Age | Director Since | | Paul M. Friedman (Chairman of the Audit Committee) | 70 | August 2016 | | Randy Maultsby | 52 | November 2021 | | Bradley E. Smith | 69 | July 2013 |

  12. Information Regarding the Nominees for Election

    Paul M. Friedman has been a member of our Board of Directors since August 2016 and was appointed Chairman of the Audit Committee in August 2020. He was the Chairman of the CNG Committee from 2016 until August 2020. From November 2009 to March 2015, Mr. Friedman served as the Senior Managing Director and Chief Operating Officer of Guggenheim Securities LLC. From June 2008 to October 2009, Mr. Friedman served as a Managing Director of Mariner Investment Group (“Mariner”). Mr. Friedman spent 27 years at Bear Stearns & Co. Inc. (“Bear Stearns”) from 1981 to 2008, most recently holding the position of Chief Operating Officer of its Fixed Income Division. Mr. Friedman serves as the Lead Director and the chairman of the Compliance Committee of Oppenheimer Holdings Inc. and is on the board of directors of Rithm Property Trust Inc. (formerly known as Great Ajax Corp.), where he is the Chairman of the board, the chair of the compensation committee and a member of the audit committee. He was also on the board of Intelligo from 2020 until September 2025. Mr. Friedman has a M.S. in Finance and Accounting from New York University, Stern School of Business, and a B.A. in Economics from Colgate University. Mr. Friedman was selected and qualified to serve as a member of our Board of Directors because of his diverse and extensive business and financial experience as well as his experience on the boards of other public companies. Randy S. Maultsby has been a member of our Board of Directors since November 2021 and has served as our President since July 2021. Previously, he served as the Company’s Managing Director. Mr. Maultsby focuses on corporate strategy and development, overseeing the Company’s acquisition, disposition and capital markets activities. Prior to joining Tiptree in 2010, Mr. Maultsby was a senior vice president in the investment banking division of Fox-Pitt, Kelton. During his investment banking career, he focused on providing strategic advice to a broad array of banks, finance, asset management and brokerage clients. Prior to joining Fox-Pitt, Kelton, Mr. Maultsby was an Associate in the M&A Group at JP Morgan and an analyst in the Financial Institutions Group at Citigroup. He was a member of the Board of Directors of Invesque Inc. from February, 2018 until April, 2024 where he served on the audit committee. Mr. Maultsby received his B.A. in Political Science, with Honors, from Hampton University. Mr. Maultsby was selected and qualified to serve as a member of our Board of Directors because of his extensive senior level experience in the capital market industry and his extensive knowledge of our business and industries. Bradley E. Smith has been a member of our Board of Directors since July 2013. Mr. Smith was a member of the board of directors of TFP, Tiptree’s predecessor, from June 2007 to July 2013. He is the founder of Kahala Capital Advisors LLC, a private investment firm, and of Kahala Aviation Ltd., a commercial aircraft leasing company. Prior to Kahala Capital Advisors LLC, Mr. Smith worked for almost 20 years in banking in New York and Asia. He was employed from 1995 until 2000 at Bear Stearns, where he started its credit derivatives businesses in New York; and later as a Senior Managing Director, based in Tokyo, managing the firm’s fixed income and derivative businesses. Before Bear Stearns, Mr. Smith spent 10 years with Bankers Trust Company (“Bankers Trust”) as a syndicate manager in its loan syndications group, where he was responsible for the syndication of some of the largest leveraged loan financings ever completed. Afterwards, he transferred to Tokyo and later to Hong Kong, where he was involved in Bankers Trust’s credit trading businesses in Asia. In his last position at Bankers Trust, Mr. Smith was one of the founders of that bank’s credit derivatives business. He has served in the past on a variety of fund boards and investment committees including Tricadia Credit Strategies Ltd. until August 2019, and is currently on the board of trustees of the Hawai’i Nature Conservancy. Mr. Smith holds a B.A. from St. Joseph’s University and an M.B.A. from the American Graduate School of International Management. Mr. Smith was selected and qualified to serve as a member of our Board of Directors because of his knowledge as a private investor and entrepreneur, experience involving large complex financial transactions and his extensive international relationships.

  13. PROPOSAL 2: APPROVAL OF AN AMENDMENT TO THE COMPANY’S 2017 OMNIBUS INCENTIVE PLAN

    PROPOSAL 2: APPROVAL OF AN AMENDMENT TO THE COMPANY’S 2017 OMNIBUS INCENTIVE PLAN We are asking stockholders to approve Amendment No. 2 (the “Amendment”) to the Tiptree Inc. 2017 Omnibus Incentive Plan, as amended by Amendment No. 1, effective as of June 7, 2022 (the “2017 Plan”), which amends the 2017 Plan to (i) extend the term of the 2017 Plan to June 6, 2037, subject to earlier termination by the Board, and (ii) increase the number of shares available for issuance thereunder by 4,000,000 shares. As of February 28, 2026, 413,369 shares remained available for future grants under the 2017 Plan, which is our only incentive award plan with shares available for issuance. Our Board of Directors and CNG Committee believe that extending the term of the 2017 Plan past June 6, 2027 and also increasing the reserve of shares for future grants is necessary to ensure that the Company has a sufficient number of shares available to attract and retain the services of key individuals essential to the Company’s long-term growth and success. No other material changes to the 2017 Plan are proposed. A copy of the Amendment is attached to this Proxy Statement as Annex A, and the discussion in this proposal is qualified in its entirety by the full text of the Amendment. The Amendment was adopted by our Board of Directors, upon recommendation from our CNG Committee on February 24, 2026, subject to stockholder approval. Currently, the 2017 Plan automatically expires on June 6, 2027 and provides that the maximum number of shares available for issuance pursuant to awards issued thereunder is 10,100,000 shares of our common stock. If our stockholders do not approve the Amendment, the Amendment will not become effective, the 2017 Plan will continue in effect (without giving effect to the Amendment), and will automatically expire on June 6, 2027 and we will be subject to the current share limit set forth in the 2017 Plan. The material features of the 2017 Plan as amended by the Amendment are described under “Summary of the 2017 Plan as Amended” below.

  14. Rationale for the Amendment

    Rationale for the Amendment During the beginning of 2026, in its determination to recommend that the Board adopt the Amendment, the CNG Committee considered advice and input presented by management with the assistance of Compensation Advisory Partners LLC (“CAP”) as its independent compensation consultant. Our Board of Directors believes that equity awards are a critical part of our compensation program and allow us to attract and retain key talent, incentivize sustainable growth and long-term value creation, and align the interests of our employees with those of our stockholders. Our Board of Directors approved the Amendment because the 2017 Plan is set to expire on June 6, 2027 and in connection with extending the plan, the Board believes, based in part on input from CAP, that we do not currently have a sufficient number of shares available under the 2017 Plan to continue to grant equity awards in line with our historical practices. As of February 28, 2026, a total of 413,369 shares remain available for issuance under the 2017 Plan, which is our only incentive award plan with shares available for issuance. As Tiptree pursues opportunities to acquire operating businesses to replace the revenues and cash flow from the sale of Fortegra, the Board believes that adding 4,000,000 shares to the 2017 Plan will provide needed flexibility to use long-term equity incentives to attract, recruit and retain key management personnel both at acquired businesses and within Tiptree, whose leadership is essential to driving sustainable growth and long-term value creation for our stockholders. Furthermore, increasing the share reserve under the 2017 Plan will enhance our competitiveness in the M&A market by enabling us to use equity as a key tool to retain the management teams that will lead the acquired businesses and recruit new talent. Furthermore, it allows us to preserve cash at Tiptree that can be deployed to fund strategic transactions and integration initiatives rather than be used for upfront compensation. While we have not identified specific acquisition targets at this time, approval of the share increase will provide the Company with flexibility to respond quickly to opportunities and to structure long‑term, performance‑linked equity incentives that align management’s interests with those of our stockholders, support retention through integration periods, and reinforce our consistent pay‑for‑performance philosophy. Our CNG Committee will continue to administer the 2017 Plan with a focus on market‑appropriate burn‑rate and dilution levels, robust vesting and performance conditions, and the use of equity in lieu of cash where it is capital‑efficient and accretive to long‑term stockholder value. No other material changes to the 2017 Plan are proposed. As of February 28, 2026, the last reported sale price of our common stock on Nasdaq was $17.03 per share. In setting the size of the share pool under the Amendment, the Board of Directors considered the historical amounts of equity awards granted by the Company in the last three years as well as the grants of PRSUs made in 2021, 2022 and 2024. In fiscal 2023, 2024 and 2025, we made equity awards under the 2017 Plan totaling 111,427 shares, 1,503,565 shares, and 296,043 shares, respectively. Of the 1,503,565 shares granted in 2024, 1,420,833 shares consisted of PRSUs (the “2024 PRSUs”) to Tiptree’s Executive Chairman, its Chief Executive Officer at the time, its President and its Chief Financial Officer. The 2024 PRSUs will vest upon Tiptree achieving a $70 Tiptree share price target (adjusted for dividends paid) prior to the tenth anniversary of the date of grant and are intended to cover three years of long-term incentive awards and none of those individuals will receive another award under the long-term incentive program until 2027. In 2021, a total of 3,500,000 PRSUs were granted to our Executive Chairman, our then Chief Executive Officer and our President (the “2021 PRSUs” and together with the 2024 PRSUs, the “PRSUs”) and an additional 350,000 PRSUs were awarded to our Chief Financial Officer in October 2022. On January 1, 2024, a total of 1,420,833 PRSUs were granted to our Executive Chairman, our then Chief Executive Officer, our President and our Chief Financial Officer. The 2024 PRSUs vest into shares of common stock upon Tiptree’s 30 trading day average stock price of $70, reduced by the aggregate amount of dividends paid. The 4,520,833 outstanding PRSUs vest into shares of common stock upon Tiptree’s 30 trading day average stock price achieving each of four stock price milestones ranging from $30 to $70, reduced by the aggregate amount of dividends paid. The PRSUs when granted were intended to cover three years of equity compensation for such recipients. The PRSU awards are intended to pay out only upon the delivery of extraordinary performance (i.e., annualized total shareholder returns of ~20% for the 2021 PRSUs and ~14% for the 2024 PRSUs). If the Company does not meet the target stock price goals over the 10-year performance period from grant date, then the PRSUs will not result in any incremental dilution. The below table illustrates the aggregate number of PRSUs that will vest upon the achievement of each remaining Tiptree share price target. Such price targets will be adjusted down for cumulative dividends paid by the Company since grant (e.g., the next share price target for the 2021 PRSUs is $28.83 as adjusted for cumulative dividends paid to date). As the table shows, the PRSUs only vest upon extraordinary total shareholder returns yielding substantial increases in Tiptree’s market value at achievement of each price target. In other words, Tiptree’s market value would need to increase at a minimum of approximately $2.6 billion in order for all the PRSUs to vest.

  15. Rationale for the Amendment

    (1) Based on a weighted average grant date closing stock price of $9.82 for the $30, $45 and $60 tranche PRSUs and a grant date closing price of $18.96 for the $70 tranche PRSUs. (2) Based on 37,877,057 shares outstanding as of February 28, 2026, the increase in Tiptree’s market value at achieving each price target as compared to a weighted average grant date closing stock price of $9.82 for the $30, $45 and $60 tranche PRSUs and $18.96 for the $70 tranche PRSUs, assuming in each case that Tiptree’s shares outstanding increases solely to include the incremental common stock issued for vested PRSUs at achievement of each price target. (3) At the $30 price target, this is based on 37,877,057 shares outstanding as of February 28, 2026. At each subsequent price target, the shares outstanding is increased solely to include the incremental common stock issued for vested PRSUs at achievement of each price target. Our three-year average burn rate — the number of RSUs and PRSUs granted in each fiscal year divided by the weighted shares of our common stock outstanding at fiscal year end is 1.73%. This burn rate is consistent with our historical average. In setting the size of the share pool under the Amendment, the Board of Directors also considered the total amount of equity awards outstanding under existing grants as of February 28, 2026, as further shown in the chart below. Based on an analysis by CAP of the remaining shares available under the 2017 Plan, the number of equity awards outstanding under the 2017 Plan, our historic burn rate, current and proposed plan features and the equity plan guidelines established by proxy advisory firms, the Board of Directors approved the Amendment and the share pool authorized under it to ensure that we continue to have the ability to provide competitive levels of equity compensation. If the Amendment is not approved by our stockholders, the 2017 Plan will continue in effect (without giving effect to the Amendment) until it automatically terminates on June 6, 2027, and we will be subject to the current share limit set forth in the 2017 Plan, which would be insufficient to continue to grant equity awards at our current levels and will materially affect our ability to attract and retain key talent. We believe that the extension of the 2017 Plan and the increase in shares available for issuance as proposed by the Amendment is reasonable, appropriate, and in the best interests of our stockholders.

  16. Dilution and Overhang

    | | Number of shares of common stock | Overhang percentage based on 47,902,058 shares outstanding | | Unvested RSUs Outstanding | 188,647 | 0.39% | | Unexercised Options Outstanding | 902,152 | 1.88% | | Unvested PRSUs Outstanding | 4,520,833 | 9.44% | | Total Shares Subject to Outstanding Awards | 5,611,632 | 11.71% | | Shares Available for Issuance Under the 2017 Plan | 413,369 | 0.86% | | Total Overhang | 6,025,001 | 12.58% | | Additional Shares Requested | 4,000,000 | 8.35% | | Total Overhang and Additional Shares Requested | 10,025,001 | 20.93% |

  17. THE BOARD OF DIRECTORS UNANIMOUSLY RECOMMENDS THAT THE STOCKHOLDERS VOTE “THREE YEARS” WITH RESPECT TO PROPOSAL 5

    This Compensation Discussion and Analysis (“CD&A”) describes our executive compensation philosophy and program, and the compensation-related decisions made by our CNG Committee with respect to performance year 2025. The discussion below is intended to help you understand the detailed information for our named executive officers (“NEOs”) provided in the executive compensation tables that follow this discussion and to help place the specific pay decisions made for 2025 performance in context within our overall compensation program. Our NEOs in 2025 are Michael Barnes, our Chairman and Chief Executive Officer, Jonathan Ilany, our Chief Executive Officer until December 31, 2025, Randy Maultsby, our President, Scott McKinney, our Chief Financial Officer and Neil Rifkind, our General Counsel and Secretary, until December 5, 2025. Effective December 5, 2025, Mr. Rifkind ceased to be our General Counsel and Secretary. Pursuant to a Separation Agreement dated as of December 5, 2025 (the “Separation Agreement”) and consistent with the severance provisions in Mr. Rifkind’s employment agreement for a termination without cause, Mr. Rifkind is entitled to certain payments and benefits in connection with his separation from service, including cash severance, payment of the Company-portion of COBRA premiums for a certain period of time following termination and continued vesting of his outstanding equity awards in accordance with the terms and conditions set forth in the award agreements evidencing such awards. Please see “Potential Payments to Named Executive Officers Upon Termination or Change in Control — Neil Rifkind” for more information. Effective December 31, 2025, Mr. Ilany ceased to be our Chief Executive Officer and effective January 1, 2026, Mr. Barnes, our Executive Chairman also became the Company’s Chief Executive Officer. Following such transition, Mr. Ilany will provide consulting and advisory services to the Company to assist with the transition of his duties and responsibilities for one year beginning January 1, 2026 (the “Advisory Period”) pursuant to an advisor agreement entered into between the Company and Mr. Ilany dated December 16, 2025 (the “Advisor Agreement”). Pursuant to the terms of the Advisor Agreement, Mr. Ilany will be entitled to, subject to the terms and conditions of the Advisor Agreement, (i) a fee of $500,000 payable in connection with Mr. Ilany’s advisory services and for serving as Vice Chairman and a director of the Board during the Advisory Period; (ii) an annual bonus in respect of the fiscal year ending December 31, 2025, payable in cash or shares as determined by the CNG, in an amount determined by the CNG based on the Company’s achievement of specific annual corporate performance objectives determined by the CNG; (iii) a cash incentive of 3.5% of Adjusted EBITDA of the Company (as publicly reported by the Company) for the fiscal year ending December 31, 2026; and (iv) at the Company’s discretion, continued participation in the Company’s group health plans or participation in COBRA benefits, with the payment of the cost of his premiums associated with such coverage borne by the Company through the earlier of December 31, 2026 and Mr. Ilany first becoming eligible for comparable coverage with a subsequent employer or otherwise ceasing to be eligible for COBRA coverage.

  18. Guiding Principles and Compensation Policies

    | Element | Form of Compensation | Pay for Performance | Primary Objectives | | Base Salary | Fixed Cash | Adjustments to base salary take into account individual performance | Attract and retain talented executives while avoiding a high fixed cost structure | | Annual Cash Incentive Awards | Variable Cash | Awards based on an earnings metric of the Company, as adjusted by the CNG Committee, and individual performance | Reward the achievement of key short-term metrics | | Long-Term Equity Incentive Awards | Variable Performance restricted stock units (“PRSUs”) vest based on achieving share price targets | Value achieved depends on increasing stock price and generating long-term stockholder value | Align executive interests with long-term stockholder value creation. | | | Restricted stock units (“RSUs”) subject to time-based vesting | Time-based vesting encourages retention; potential increased value achieved through stock appreciation | |

  19. Guiding Principles and Compensation Policies

    | What We Do | | | | | ✓ | Pay for performance | ✓ | Use an independent compensation consultant | | ✓ | Grant equity-based awards as a significant portion of our NEOs annual variable compensation | ✓ | Prohibit NEOs from shorting or hedging Tiptree stock (see “Corporate Governance Matters - Restrictions on Hedging and Pledging Transactions”) | | ✓ | Mitigate risk through a clawback policy | ✓ | CNG Committee reserves right to exercise negative discretion | | ✓ | Individual grant limits under our 2017 Omnibus Incentive Plan | | |

  20. Guiding Principles and Compensation Policies

    | What We Don’t Do | | | | | ✓ | No Section 280G or 409A tax gross-ups in executive employment agreements | ✓ | No recycling of shares used to pay the taxes on vested RSUs | | ✓ | No defined benefit pensions or supplemental retirement programs | ✓ | No repricing of underwater stock options | | ✓ | No guaranteed bonus arrangements with our NEOs | | |

  21. Named Executive Officers

    Named Executive Officers Our NEOs are the executive officers whose compensation is discussed in this CD&A and whose compensation is shown in the accompanying compensation tables. For 2025, our NEOs are listed in the table below, which shows the base salary and incentive compensation awarded to our NEOs for their performance in 2025 in the manner that it was considered by the CNG Committee. When we refer to the total compensation figures of our NEOs as they relate to 2025 in this CD&A we are referring to annual base salary paid in 2025, and cash bonuses for 2025 performance but paid in early 2026. For purposes of determining annual equity grants to our NEOs, our CNG Committee starts with a dollar amount (the “Par Value”) and determines the number of shares based on the volume weighted average price (the “VWAP”) of the Company's common stock for the 10 trading days prior to the grant date. The amounts presented below with respect to the stock awards are the Par Value of such grants. These amounts differ from the amounts for the same columns included in the Summary Compensation Table because they are valued using a different valuation method and because SEC rules require us to include the grant date fair value of equity awards based on the date of actual grant rather than the performance year in which they were earned. For example, the awards shown in the Summary Compensation Table for 2025 were granted in such year but were based on 2024 performance. On January 1, 2024, the Company granted Messrs. Barnes, Ilany, Maultsby and McKinney an aggregate of 1,420,833 PRSUs, which are intended to cover three years of long-term incentive awards. Messrs. Barnes, Maultsby and McKinney will not receive another award under the long-term incentive program until 2027. For purposes of the Summary Compensation Table, such PRSUs were valued using the grant date fair value, as estimated on the date of grant using a Black-Scholes-Merton option pricing formula embedded within a Monte Carlo model used to simulate the future stock prices of Tiptree, which assumes that the market requirement is achieved. For more detail, including the underlying valuation assumptions for PRSUs, please see Note 10 — Stock Based Compensation, to our consolidated financial statements in our 2025 Annual Report on Form 10-K.

  22. (CNG Perspective; Not a Substitute for the Summary Compensation Table)

    | Name and Title | Performance Year | Salary ($) | Non-Equity Incentive Plan Compensation ($) | Stock Awards(1) ($) | Option Awards(1) ($) | Other Compensation(2) | Total ($) | | | 2025 | $1,200,000 | $5,651,620 | $— | — | $45,846 | $6,897,466 | | Michael G. Barnes | 2024 | $1,100,000 | $— | $5,146,815 | — | $81,324 | $6,328,139 | | Chairman and Chief Executive Officer | 2023 | $1,000,000 | $4,382,697 | $— | — | $61,998 | $5,444,695 | | | 2025 | $1,200,000 | $5,651,620 | $— | — | $137,811 | $6,989,431 | | Jonathan Ilany | 2024 | $1,100,000 | $2,001,319 | $7,179,979 | — | $139,201 | $10,420,499 | | Former Chief Executive Officer | 2023 | $1,000,000 | $4,382,697 | $— | — | $142,867 | $5,525,564 | | | 2025 | $600,000 | $1,750,000 | $— | — | $11,583 | $2,361,583 | | Randy Maultsby | 2024 | $500,000 | $1,750,000 | $1,274,006 | — | $10,725 | $3,534,731 | | President | 2023 | $500,000 | $1,600,000 | $— | — | $9,326 | $2,109,326 | | | 2025 | $500,000 | $1,250,000 | $— | — | $11,583 | $1,761,583 | | Scott McKinney(3) | 2024 | $500,000 | $1,250,000 | $1,047,500 | — | $10,725 | $2,808,225 | | Chief Financial Officer | 2023 | $450,000 | $1,000,000 | $250,000 | — | $9,326 | $1,709,326 | | | 2025 | $467,949 | $— | $— | — | $1,714,091 | $2,182,040 | | Neil C. Rifkind(4) | 2024 | $500,000 | $880,000 | $440,000 | — | $100,679 | $1,920,679 | | Former VP, General Counsel and Secretary | 2023 | $500,000 | $800,000 | $400,000 | — | $71,618 | $1,771,618 |

  23. (CNG Perspective; Not a Substitute for the Summary Compensation Table)

    (1) For Mr. Barnes for 2024, this represents a combination of (a) 200,000 Tiptree shares issued on October 30, 2024 at a closing stock price of $19.72 pursuant to vested PRSUs and (b) the CNG’s decision to grant to Mr. Barnes, $1,202,815 worth of Tiptree shares on February 25, 2025 for 2024 performance. For Mr. Ilany for 2024, this represents a combination of (a) 200,000 Tiptree shares issued on October 17, 2024 at a closing stock price of $20.89 pursuant to vested PRSUs and (b) the CNG’s decision to grant to Mr. Ilany, $3,001,979 worth of Tiptree shares on February 25, 2025 for 2024 performance. For Mr. Maultsby for 2024, this represents 66,667 Tiptree shares issued on October 9, 2024 at a closing stock price of $19.11 pursuant to vested PRSUs. For Mr. McKinney for 2024, this represents 50,000 Tiptree shares issued on October 18, 2024 at a closing stock price of $20.95 pursuant to vested PRSUs and for 2023, this represents the Par Value of RSUs grants. For Mr. Rifkind, for all years, this represents the Par Value of RSU grants. (2) For Messrs. Maultsby and McKinney for 2025, 2024 and 2023 this represents premiums paid by the Company to our group health insurance provider under a medical expenses reimbursement plan (the “MERP”). Mr. Barnes’s $45,846 of other compensation in 2025 consists of $11,583 attributable to the MERP, $18,385 attributable to travel reimbursements and $15,878 of reimbursement for taxes associated with such reimbursements. Mr. Barnes’s $81,324 of other compensation in 2024 consists of $10,724 attributable to the MERP, $37,884 attributable to travel reimbursements and $32,716 of reimbursement for taxes associated with such reimbursements. Mr. Barnes’s $61,998 of other compensation in 2023 consists of $9,326 attributable to the MERP, $28,264 attributable to travel reimbursements and $24,408 of reimbursement for taxes associated with such reimbursements. Mr. Ilany’s $137,811 of other compensation in 2025 consists of $11,583 attributable to the MERP, $55,593 attributable to travel reimbursements, $12,141 that the Company paid in connection with maintaining the IT infrastructure in Mr. Ilany’s home office and $58,494 of reimbursement for taxes associated with such reimbursements. Mr. Ilany’s $139,201 of other compensation in 2024 consists of $10,724 attributable to the MERP, $54,102 attributable to travel reimbursements, $14,839 that the Company paid in connection with maintaining the IT infrastructure in Mr. Ilany’s home office and $59,536 of reimbursement for taxes associated with such reimbursements. Mr. Ilany’s $142,867 of other compensation in 2023 consists of $9,326 attributable to the MERP, $54,283 attributable to travel reimbursements, $17,375 that the Company paid in connection with maintaining the IT infrastructure in Mr. Ilany’s home office and $61,883 of reimbursement for taxes associated with such reimbursements. Mr. Rifkind’s $1,714,091 of other compensation in 2025 consists of $1,600,000 attributable to his severance payment, $11,583 attributable to the MERP, $55,006 attributable to travel reimbursements and $47,502 of reimbursement for taxes associated with such reimbursements. Mr. Rifkind’s $100,679 of other compensation in 2024 consists of $10,725 attributable to the MERP, $48,269 attributable to travel reimbursements and $41,685 of reimbursement for taxes associated with such reimbursements. Mr. Rifkind’s $71,618 of other compensation in 2023 consists of $9,326 attributable to the MERP, $33,426 attributable to travel reimbursements and $28,866 of reimbursement for taxes associated with such reimbursements. (3) Mr. McKinney’s stock award amount for performance year 2023 represent the Par Value of the RSUs issued on February 27, 2024. Mr. Rifkind’s stock award amounts for performance years 2024 and 2023 represent the Par Value of the RSU issuances on February 25, 2025 and February 27, 2024, respectively, in which the recipient in each case received matching RSUs that cliff vest after three years from the grant date and deliver two shares of Tiptree stock for each RSU; as such, the Par Value of the RSU issuances were doubled accordingly. Pursuant to the Separation Agreement, Mr. Rifkind ceased to be General Counsel and Secretary of the Company effective December 5, 2025. His salary column reflects his salary from January 1, 2025 to December 5, 2025. The remainder of his compensation paid in 2025 is reflected in the “Other Compensation” column.

  24. Use of Independent Compensation Consultant

    Use of Independent Compensation Consultant The CNG Committee engaged CAP to serve as its independent compensation consultant during 2025. CAP received instructions from, and reported to, the CNG Committee on an independent basis. CAP was also authorized by the CNG Committee to share with and request and receive from management specified information in order to prepare for CNG Committee meetings. The CNG Committee requested CAP’s advice on a variety of matters, including the design of our executive compensation program and the compensation opportunities under it, compensation strategy, market comparisons, pay and performance alignment, the advisability of peer benchmarking, executive pay trends, compensation best practices, compensation-related legislative updates and related rulemaking, and compensation plan designs and modifications. The CNG Committee met with CAP, both with and without management present, on several occasions during 2025 with respect to compensation decisions for 2025 performance. The CNG Committee assessed the independence of CAP pursuant to SEC and Nasdaq rules, and concluded that no conflict of interest exists that would prevent CAP from independently representing the CNG Committee. During 2025, CAP did not provide any services to the Company or its affiliates other than advising the CNG Committee on executive officer compensation. The CNG Committee does not currently use benchmarking or comparative data in making compensation decisions. In 2025, however, the CNG Committee reviewed compensation practices compiled by CAP with respect to the companies that operate in the same industries as the Company to provide a reference point for pay levels and practices, including practices relating to the grant of performance-vesting equity awards.

  25. 2025 Executive Compensation Program and Decisions

    (1) Effective December 31, 2025, Mr. Ilany ceased to be our Chief Executive Officer. (2) Effective December 5, 2025, Mr. Rifkind ceased to be our General Counsel and Secretary. Incentive Compensation-Pool Determination The CNG Committee uses Adjusted EBITDA as the metric to determine annual incentive compensation for the Company’s executive officers and as its primary pay for performance measure. The CNG Committee previously established a 2025 cash incentive compensation pool for Messrs. Barnes and Ilany equal to 7.0% of Adjusted EBITDA prior to the payment of the incentive compensation of Messrs. Barnes and Ilany, which was allocated 3.5% to Michael Barnes, Chairman and Chief Executive Officer, and 3.5% to Jonathan Ilany, our former Chief Executive Officer. Adjusted EBITDA is defined as GAAP net income plus corporate interest expense (excluding interest expense associated with corporate debt at the holding company level), plus income taxes, plus depreciation and amortization expense, plus non-cash fair value adjustments including changes in the fair value of the Additional Fortegra Warrant liability (excluding in 2025), plus significant non-recurring expenses consisting of acquisition, start-up and disposition costs, including debt extinguishment, legal, taxes, banker fees and other costs (excluding in 2025), and plus unrealized gains (losses) on available for sale securities, the pre-tax gain recorded directly to stockholders’ equity related to the 2022 Warburg transaction and changes in unrealized currency translation adjustments reported in other comprehensive income. For a reconciliation to Adjusted EBITDA from GAAP financials, see “Annex B: Non-GAAP Measures.” The CNG Committee believes Adjusted EBITDA reflects a total return of the Company’s income from business operations, investment activity and capital allocation to assets. Incentive Compensation-Pool Determination — Other NEOs The bonus amounts for Messrs. Maultsby and McKinney were determined by the CNG Committee in its discretion in consultation with Messrs. Barnes and Ilany, based 50% on the Company’s Adjusted EBITDA relative to the prior year and 50% on the CNG Committee’s qualitative assessment of individual performance for 2025 considering the NEO’s role, leadership responsibilities and retention considerations. Incentive Compensation-Performance-Based Annual Cash Incentive Awards — NEOs For 2025, the performance-based annual cash incentive award allocation to the NEOs were as follows:

  26. 2025 Executive Compensation Program and Decisions

    | Name | Annual Cash Incentive Award | | Michael Barnes | $5,651,620 | | Jonathan Ilany | $5,651,620 | | Randy Maultsby | $1,750,000 | | Scott McKinney | $1,250,000 | | Neil Rifkind(1) | $— |

  27. Summary Compensation Table

    Summary Compensation Table

  28. Summary Compensation Table

    | Name and Title | Year | Salary($) | Bonus ($) | Stock Awards ($)(1) | Option Awards ($)(1) | Non-Equity Incentive Plan Compensation(2) | All Other Compensation ($)(3) | Total ($) | | | 2025 | $1,200,000 | — | $1,317,818 | — | $5,651,620 | $45,846 | $8,215,284 | | Michael G. Barnes(4) | 2024 | $1,100,000 | — | $5,753,000 | — | $— | $81,324 | $6,934,324 | | Chairman and Chief Executive Officer | 2023 | $1,000,000 | — | $— | — | $4,382,697 | $61,998 | $5,444,695 | | | 2025 | $1,200,000 | — | $3,289,029 | — | $5,651,620 | $137,811 | $10,278,460 | | Jonathan Ilany(5) | 2024 | $1,100,000 | — | $5,753,000 | — | $2,001,319 | $139,201 | $8,993,520 | | Former Chief Executive Officer | 2023 | $1,000,000 | — | $— | — | $4,382,697 | $142,867 | $5,525,564 | | | 2025 | $600,000 | — | $— | — | $1,750,000 | $11,583 | $2,361,583 | | Randy Maultsby(6) | 2024 | $500,000 | — | $1,917,663 | — | $1,750,000 | $10,725 | $4,178,388 | | President | 2023 | $500,000 | — | $— | — | $1,600,000 | $9,326 | $2,109,326 | | | 2025 | $500,000 | — | $— | — | $1,250,000 | $11,583 | $1,761,583 | | Scott McKinney(7) | 2024 | $500,000 | — | $1,438,250 | — | $1,250,000 | $10,725 | $3,198,975 | | Chief Financial Officer | 2023 | $450,000 | — | $252,337 | — | $1,000,000 | $9,326 | $1,711,663 | | Neil C. Rifkind(8) | 2025 | $467,949 | — | $482,071 | — | $— | $1,714,091 | $2,664,111 | | Former VP, General Counsel and Secretary | 2024 | $500,000 | — | $422,308 | — | $880,000 | $100,679 | $1,902,987 | | | 2023 | $500,000 | — | $378,489 | — | $800,000 | $71,618 | $1,750,107 |

  29. Summary Compensation Table

    (1) For 2025 for Messrs. Barnes and Ilany, amounts in this column represent the grant date fair value of 60,813 and 151,778 Tiptree shares issued to Messrs. Barnes and Ilany, respectively, for their 2024 performance. Such shares were issued as of February 25, 2025 at a closing stock price of $21.67 per share. For 2025 for Mr. Rifkind and for all the NEOs for all other periods, amounts in this column represent the aggregate grant date fair value of PRSUs or RSUs, computed in accordance with FASB ASC Topic 718. RSUs are valued using the closing price of our common stock on the grant date. The fair value of the PRSUs was estimated on the date of grant using a Black-Scholes-Merton option pricing formula embedded within a Monte Carlo model used to simulate the future stock prices of Tiptree, which assumes that the market requirement is achieved. For more detail, including the underlying valuation assumptions for PRSUs and stock option awards, please see Note 10, Stock Based Compensation, to our consolidated financial statements in our 2025 Annual Report on Form 10-K. Pursuant to SEC rules, the amounts shown exclude the impact of estimated forfeitures related to service-based vesting conditions. (2) Represents the dollar value of cash incentive awards earned in the performance year but paid in the first quarter of the following year. For Messrs. Maultsby and McKinney for 2025, 2024 and 2023 this represents premiums paid by the Company to our group health insurance provider under a medical expenses reimbursement plan (the “MERP”). Mr. Barnes’s $45,846 of other compensation in 2025 consists of $11,583 attributable to the MERP, $18,385 attributable to travel reimbursements and $15,878 of reimbursement for taxes associated with such reimbursements. Mr. Barnes’s $81,324 of other compensation in 2024 consists of $10,724 attributable to the MERP, $37,884 attributable to travel reimbursements and $32,716 of reimbursement for taxes associated with such reimbursements. Mr. Barnes’s $61,998 of other compensation in 2023 consists of $9,326 attributable to the MERP, $28,264 attributable to travel reimbursements and $24,408 of reimbursement for taxes associated with such reimbursements. Mr. Ilany’s $137,811 of other compensation in 2025 consists of $11,583 attributable to the MERP, $55,593 attributable to travel reimbursements, $12,141 that the Company paid in connection with maintaining the IT infrastructure in Mr. Ilany’s home office and $58,494 of reimbursement for taxes associated with such reimbursements. Mr. Ilany’s $139,201 of other compensation in 2024 consists of $10,724 attributable to the MERP, $54,102 attributable to travel reimbursements, $14,839 that the Company paid in connection with maintaining the IT infrastructure in Mr. Ilany’s home office and $59,536 of reimbursement for taxes associated with such reimbursements. Mr. Ilany’s $142,867 of other compensation in 2023 consists of $9,326 attributable to the MERP, $54,283 attributable to travel reimbursements, $17,375 that the Company paid in connection with maintaining the IT infrastructure in Mr. Ilany’s home office and $61,883 of reimbursement for taxes associated with such reimbursements. Mr. Rifkind’s $1,714,091 of other compensation for 2025 consists of $1,600,000 attributable to his severance payment, $11,583 attributable to the MERP, $55,006 attributable to travel reimbursements and $47,502 of reimbursement for taxes associated with such reimbursements. Mr. Rifkind’s $100,679 of other compensation in 2024 consists of $10,725 attributable to the MERP, $48,269 attributable to travel reimbursements and $41,685 of reimbursement for taxes associated with such reimbursements. Mr. Rifkind’s $71,618 of other compensation in 2023 consists of $9,326 attributable to the MERP, $33,426 attributable to travel reimbursements and $28,866 of reimbursement for taxes associated with such reimbursements. Mr. Barnes’s stock award amount in 2024 represents the grant date fair value of the 550,000 PRSUs granted on January 1, 2024. (5) Mr. Ilany’s stock award amount in 2024 represents the grant date fair value of the 550,000 PRSUs granted on January 1, 2024. (6) Mr. Maultsby’s stock award amount in 2024 represents the grant date fair value of the 183,333 PRSUs granted to him on January 1, 2024. (7) Mr. McKinney’s stock award amount in 2024 represents the grant date fair value of the 137,500 PRSUs granted to him on January 1, 2024. Mr. McKinney’s stock award amount in 2023 represents the grant date fair value of RSUs granted to him on February 22, 2023. (8) Mr. Rifkind’s stock award amounts for performance years 2024 and 2023 represent the Par Value of the RSU issuances on February 25, 2025 and February 27, 2024, respectively, in which he received matching RSUs that cliff vest after three years from the grant date and deliver two shares of Tiptree stock for each RSU; as such, the Par Value of the RSU issuances were doubled accordingly. Pursuant to the Separation Agreement, Mr. Rifkind ceased to be General Counsel and Secretary of the Company effective December 5, 2025. His salary column reflects his salary from January 1, 2025 to December 5, 2025. The remainder of his compensation paid in 2025 is reflected in the “Other Compensation” column.

  30. Grants of Plan-Based Awards

    Grants of Plan-Based Awards The following table provides additional information about non-equity and equity-based awards granted to our NEOs during the year ended December 31, 2025:

  31. Grants of Plan-Based Awards

    | | Estimated Future Payouts Under Non-Equity Incentive Plan Awards(1) | | | | All Other Stock Awards: Number of Shares of Stock | Grant Date Fair Value(3) | | Name | Threshold | Target | Maximum | Grant Date | or Units(2) | ($) | | Michael G. Barnes | — | $5,651,620 | — | 2/25/2025 | 60,813 | $1,317,818 | | Jonathan Ilany (4) | — | $5,651,620 | — | 2/25/2025 | 151,778 | $3,289,029 | | Randy Maultsby | — | — | — | | — | $— | | Scott McKinney | — | — | — | | — | — | | Neil C. Rifkind (5) | — | — | — | 2/25/2025 | 22,246 | $482,071 |

  32. Grants of Plan-Based Awards

    (1) For Messrs. Barnes and Ilany, the dollar figures in the table above represent the incentive compensation pool based on a percentage of 2025 Adjusted EBITDA which have not yet been paid. The actual amounts granted to Messrs. Maultsby and McKinney were subject to the discretion of the Executive Chairman and CEO and, as such, do not have calculable threshold, target or maximum estimated payouts. (2) On February 25, 2025, Messrs. Barnes and Ilany were granted common stock. On February 25, 2025, Mr. Rifkind was granted matching RSUs, which will cliff vest on February 28, 2028, subject to certain terms contained in the award agreements. (3) The grant date fair value of the common stock granted to Messrs. Barnes and Ilany, and the fair value of the RSUs granted to Mr. Rifkind is computed in accordance with FASB ASC Topic 718. RSUs and common stock are valued using the closing price of our common stock on the grant date ($21.67 per share). Pursuant to SEC rules, the amounts shown exclude the impact of estimated forfeitures related to service-based vesting conditions. (4) Mr. Ilany ceased to be our Chief Executive Officer after December 31, 2025. (5) Effective December 5, 2025, Mr. Rifkind ceased to be our General Counsel and Secretary. Narrative Disclosure to Summary Compensation Table and Grants of Plan-Based Awards Table Below is a brief description of the material terms of our NEOs’ employment agreements. There are no definite terms under the employment agreements, and the Company could have terminated each such NEO’s employment at any time upon approval of the Board of Directors, provided that, if such NEO’s employment had been terminated without cause or he or she resigned for good reason (as defined in the Employment Agreement), then such NEO would have been entitled, subject to the execution of a general release, to certain severance payments as described in more detail below in “—Potential Payments to Named Executive Officers Upon Termination or Change in Control.” The Employment Agreements also include non-compete, non-solicitation, non-disparagement and confidentiality provisions during our NEO’s employment and for a specified period of time following the date of termination. Michael Barnes — Chairman and Chief Executive Officer Under Mr. Barnes’s Executive Employment Agreement dated as of February 1, 2018, Mr. Barnes receives compensation for serving as Executive Chairman of Tiptree, consisting of an annual base salary ($1,200,000 for 2025) and a discretionary annual cash bonus in an amount set by the CNG Committee. Mr. Barnes is also eligible to participate in any stock option, restricted stock, equity compensation or other long-term incentive plan of Tiptree pursuant to the terms and conditions of such plan then in effect. Mr. Barnes was appointed our Chief Executive Officer effective January 1, 2026. Jonathan Ilany — Former Chief Executive Officer Effective December 31, 2025, Mr. Ilany ceased to be our Chief Executive Officer and Mr. Barnes, our Executive Chairman became the Company’s Chief Executive Officer. Following such transition, Mr. Ilany will provide consulting and advisory services to the Company to assist with the transition of his duties and responsibilities for the Advisory Period. Pursuant to the terms of the Advisor Agreement, Mr. Ilany will be entitled to, subject to the terms and conditions of the Advisor Agreement, (i) a fee of $500,000 payable in connection with Mr. Ilany’s advisory services and for serving as Vice Chairman and a director of the Board during the Advisory Period; (ii) an annual bonus in respect of the fiscal year ending December 31, 2025, payable in cash or shares as determined by the CNG, in an amount determined by the CNG based on the Company’s achievement of specific annual corporate performance objectives determined by the CNG; (iii) a cash incentive of 3.5% of Adjusted EBITDA of the Company (as publicly reported by the Company) for the fiscal year ending December 31, 2026; and (iv) at the Company’s discretion, continued participation in the Company’s group health plans or participation in COBRA benefits, with the payment of the cost of his premiums associated with such coverage borne by the Company through the earlier of December 31, 2026 and Mr. Ilany first becoming eligible for comparable coverage with a subsequent employer or otherwise ceasing to be eligible for COBRA coverage. Randy Maultsby — President Under Mr. Maultsby’s Executive Employment Agreement dated as of July 14, 2021, Mr. Maultsby receives an annual base salary ($600,000 for 2025) and a discretionary annual cash bonus in an amount set by the CNG Committee. Mr. Maultsby is also eligible to participate in any stock option, restricted stock, equity compensation or other long-term incentive plan of Tiptree pursuant to the terms and conditions of such plan then in effect. Scott McKinney — Chief Financial Officer Under Mr. McKinney’s Executive Employment Agreement dated as of October 14, 2022, Mr. McKinney receives an annual base salary ($500,000 for 2025) and a discretionary annual cash bonus in an amount set by the CNG Committee. Mr. McKinney is also eligible to participate in any stock option, restricted stock, equity compensation or other long-term incentive plan of Tiptree pursuant to the terms and conditions of such plan then in effect. Neil Rifkind — Former Vice President, General Counsel and Secretary Mr. Rifkind separated from the Company effective December 5, 2025. Please see “Potential Payments to Named Executive Officers Upon Termination or Change in Control — Neil Rifkind” for more information.

  33. Outstanding Equity Awards at Fiscal Year-End

    Outstanding Equity Awards at Fiscal Year-End The following table sets forth outstanding stock options (both exercisable and unexerciseable), unvested RSUs and unvested PRSUs held by our NEOs as of December 31, 2025. The unearned PRSUs granted in 2021 (the “2021 PRSUs”) will vest upon Tiptree achieving each of three remaining Tiptree share price target milestones ranging from $30 to $60 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant and the unearned PRSUs granted in 2024 (the “2024 PRSUs”) will vest upon Tiptree achieving a $70 Tiptree share price target (adjusted for dividends paid) prior to the tenth anniversary of the date of grant. Any of the unvested 2021 PRSUs shall expire on August 4, 2031 and any of the unvested 2024 PRSUs shall expire on January 1, 2034.

  34. Outstanding Equity Awards at Fiscal Year-End

    | | Option Awards | | | | | Stock Awards | | | | | Name | Grant Date | Number of Securities Underlying Unexercised Options (#) Exercisable | Number of Securities Underlying Unexercised Options (#) Unexercisable(1) | Option Exercise Price(2) ($) | Option Expiration Date | Number of shares or units of stock that have not vested (#) | Market value of shares or units of stock that have not vested ($)(3) | Equity incentive plan awards: Number of unearned shares that have not vested (#)(4) | Equity incentive plan awards: Market or payout value of unearned shares that have not vested ($)(4) | | | 2/26/2018 | 93,332 | — | $5.85 | 2/26/2028 | | | 1,750,000 | $8,906,480 | | Michael G. Barnes | 2/26/2019 | 90,326 | — | $6.26 | 2/26/2029 | | | | | | | 2/20/2020 | 170,111 | — | $7.25 | 2/20/2030 | | | | | | | 2/26/2018 | 149,331 | — | $5.85 | 2/26/2028 | | | 1,750,000 | $8,906,480 | | Jonathan Ilany | 2/26/2019 | 135,489 | — | $6.26 | 2/26/2029 | | | | | | | 2/20/2020 | 255,166 | — | $7.25 | 2/20/2030 | | | | | | Randy Maultsby | | — | — | $- | — | — | $— | 583,333 | $2,968,823 | | Scott McKinney | | — | — | $- | — | 15,110(5) | $276,059 | 437,500 | $2,226,620 | | Neil C. Rifkind | | — | — | $- | — | 68,702(6) | $1,255,185 | — | $— |

  35. Outstanding Equity Awards at Fiscal Year-End

    (1) All outstanding and unexercised stock options have met their performance-based vesting requirements and time-based vesting requirements. (2) Based on the common stock closing price on the date such options are granted. (3) Based on the common stock closing price of $18.27 on December 31, 2025 (the last trading day of the year). (4) Consists of the remaining unvested 2021 PRSUs and the 2024 PRSUs that vest upon Tiptree satisfying the relevant Tiptree share price target milestones in accordance with the terms of the respective PRSUs. The fair value of the PRSUs was estimated on the date of grant using a Black-Scholes-Merton option pricing formula embedded within a Monte Carlo model used to simulate the future stock prices of Tiptree, which assumes that the market requirement is achieved. For more detail, including the underlying valuation assumptions for PRSUs and stock option awards, please see Note 10, Stock Based Compensation, to our consolidated financial statements in our 2025 Annual Report on Form 10-K. (5) Mr. McKinney’s 15,110 unvested RSUs were granted to him on February 22, 2023 and cliff vested on February 20, 2026. (6) Mr. Rifkind’s 68,702 unvested RSUs consist of (a) 22,664 RSUs granted to him on February 22, 2023, which cliff vested on February 20, 2026, (b) 23,792 RSUs granted to him on February 27, 2024, which will cliff vest on February 20, 2027, and (c) 22,246 RSUs granted to him on February 25, 2025, which will cliff vest on February 28, 2028. Pursuant to the Separation Agreement, Mr. Rifkind ceased to be our General Counsel and Secretary on December 5, 2025 but his unvested RSUs remain eligible for RSU Vesting (defined below).

  36. Option Exercises and Stock Vested

    Option Exercises and Stock Vested The following table sets forth information with respect to our NEOs regarding common stock acquired pursuant to stock option exercises and the vesting of RSUs in 2025 on an aggregated basis.

  37. Option Exercises and Stock Vested

    | | Option Awards | | Stock Awards | | | Name | Number of Shares Acquired on Exercise (#) | Value Realized on Exercise ($)(1) | Number of Shares Acquired on Vesting (#) | Value Realized on Vesting ($) | | Michael G. Barnes(2) | 163,158 | $3,123,087 | - | $— | | Jonathan Ilany(3) | 501,897 | $8,651,077 | - | $— | | Randy Maultsby | - | $— | - | $— | | Scott McKinney(4) | - | $— | 15,736 | $304,020 | | Neil C. Rifkind(4)(5) | - | $— | 26,750 | $516,810 |

  38. Option Exercises and Stock Vested

    Value realized on exercise is calculated by multiplying the options exercised by the difference between the price of our common stock at the time of exercise and the exercise (strike) price. On September 12, 2025, Mr. Barnes exercised cashless an aggregate of 163,158 options to purchase common stock, which were granted on January 4, 2016, March 10, 2016 and February 22, 2017, with exercise strike prices at $5.67, $5.87 and $6.65, respectively, all at the exercise price of $25.49, receiving a net of 122,520 shares. (3) On September 2, 2025, Mr. Ilany exercised cashless an aggregate of 150,742 options to purchase common stock, which were granted on January 4, 2016 and March 10, 2016, with exercise strike prices of $5.67 and $5.87, respectively, all at the exercise price of $23.36 receiving a net of 60,908 shares; and on September 15, 2025 exercised cashless 351,155 options to purchase common stock, which were granted on February 22, 2017, with an exercise strike price of $6.65, at the exercise price of $23.70, receiving a net amount of 127,837 shares. On December 31, 2025, Mr. Ilany ceased to be our Chief Executive Officer. (4) Represents RSUs which vested on February 20, 2025 with a closing stock price of $19.32 on the vesting date. (5) Mr. Rifkind ceased to be our General Counsel and Secretary effective December 5, 2025.

  39. Potential Payments to Named Executive Officers Upon Termination or Change in Control

    Potential Payments to Named Executive Officers Upon Termination or Change in Control The employment agreements provide for severance payments if the employment of an NEO is terminated by the Company without “cause” (as defined in the respective employment agreement) or due to disability or death, or by such NEO for “good reason” (as defined in the respective employment agreement). Upon such a termination, then, subject to the execution of a general release, each NEO will be entitled to receive (i) a lump sum severance payment in an amount equal to (A) in the case of Mr. Barnes, (I) two times base salary and (II) the average of the annual bonuses paid to the executive with respect to the two calendar years immediately preceding the year that termination occurs, multiplied by one plus a fraction, the numerator of which is the number of full months of employment the executive completed in the year in which termination occurs and the denominator of which is twelve and (B), in the case of Messrs. Maultsby, McKinney and Rifkind (terminated December 5, 2025), one times base salary and the prior year’s annual bonus, provided that in the case of a termination of employment due to an executive’s death or disability, any severance pay will be reduced by amounts payable to an executive, or his or her estate, under an employer sponsored plan; (ii) any earned but unpaid annual bonus with respect to any performance period that ends in the calendar year prior to the calendar year in which termination occurs, payable solely in cash; (iii) full vesting with respect to the time-based vesting condition (immediately in the case of death, disability, termination without cause or termination for good reason) of any then outstanding unvested equity awards and awards subject to performance-based vesting conditions remain outstanding for their term and eligible to vest on achievement of the performance requirement; and (iv) payment of the cost of COBRA premiums above the active employee rate through the earlier of 18 months following termination and the date the executive becomes eligible for comparable coverage with a subsequent employer. We do not have severance arrangements with our NEOs in connection with a change of control. However, upon the occurrence of a change of control, RSU awards granted to the NEOs are accelerated and the time-vesting requirement of the stock options granted to our NEOs is waived (since the stock options have all met their performance requirement, upon a change of control, they will all become immediately exercisable). As used in our award agreements, the term “retirement” means the participant is at least 55 years old and satisfies the “Rule of 65” which means that the sum of the participant’s age and years of combined and continuous service with the Company equals at least sixty-five (65). For purposes of determining the Rule of 65, only full years of service with the Company shall count as years of combined and continuous service. Mr. Barnes is the only currently employed NEO who qualifies for retirement. Michael Barnes • If Mr. Barnes’s employment was terminated by the Company without cause or due to his death or disability (or he terminated employment for good reason) as of December 31, 2025, he would have been entitled to receive a total severance of $8,051,620, which represents two times his base salary and the average of his annual bonus for the past two calendar years multiplied by two. • If Mr. Barnes’s employment was terminated by the Company without cause or due to his death, disability, or retirement, or upon a change of control of the Company, all of Mr. Barnes’s stock options will be exercisable, given their performance requirements have been achieved. With respect to Mr. Barnes’s 1,750,000 unvested PRSUs as of December 31, 2025: If Mr. Barnes’s employment was terminated by the Company without cause, or due to his death or disability, or as a result of his retirement after (a) August 4, 2024 with respect to the 2021 PRSUs, then his 1,200,000 unvested 2021 PRSUs will remain outstanding and be eligible to vest upon Tiptree satisfying the relevant Tiptree share price target milestones in accordance with the terms of the 2021 PRSUs; and (b) January 1, 2027 with respect to the 2024 PRSUs, then his 550,000 unvested 2024 PRSUs will remain outstanding and be eligible to vest upon Tiptree satisfying the relevant Tiptree share price target milestones in accordance with the terms of the 2024 PRSUs. Upon a change of control, only those PRSUs that satisfy the relevant Tiptree share price target milestones from such a change of control transaction will vest, with all other PRSUs becoming forfeited unless otherwise assumed in such a change of control transaction. Randy Maultsby • If Mr. Maultsby’s employment was terminated by the Company without cause or due to his death or disability (or he terminated employment for good reason) as of December 31, 2025, he would have been entitled to receive a total severance of $2,350,000, which represents his base salary and incentive compensation for services performed in 2025. • With respect to Mr. Maultsby’s 583,333 unvested PRSUs as of December 31, 2025: o If Mr. Maultsby’s employment was terminated by the Company without cause, or due to his death or disability, then such unvested PRSUs shall remain outstanding and be eligible to vest upon Tiptree satisfying the relevant Tiptree share price target milestones in accordance with the terms of the PRSUs. o Upon a change of control, only those PRSUs that satisfy the relevant Tiptree share price target milestones from such a change of control transaction will vest, with all other PRSUs becoming forfeited unless otherwise assumed in such a change of control transaction. Scott McKinney • If Mr. McKinney’s employment was terminated by the Company without cause or due to his death or disability (or he terminated employment for good reason) as of December 31, 2025, he would have been entitled to receive a total severance of $1,750,000, which represents his base salary and incentive compensation for services performed in 2025. • If Mr. McKinney’s employment was terminated by the Company due to his death or disability, then his 15,110 unvested RSUs as of December 31, 2025, with a market value of $276,059 based on the Company’s closing stock price of $18.27 as of December 31, 2025 would vest immediately upon termination. • If Mr. McKinney’s employment was terminated by the Company without cause, then his 15,110 unvested RSUs as of December 31, 2025 would remain outstanding and vest in accordance with their vesting schedule (the “RSU Vesting”). • Upon a change of control, Mr. McKinney’s 15,110 unvested RSUs as of December 31, 2025, with a market value of $276,059 based on the Company’s closing stock price of $18.27 as of December 31, 2025, would become fully vested. • With respect to McKinney’s 437,500 unvested PRSUs as of December 31, 2025: o If Mr. McKinney’s employment was terminated by the Company without cause, or due to his death or disability, then such unvested PRSUs will remain outstanding and be eligible to vest upon Tiptree satisfying the relevant Tiptree share price target milestones in accordance with the terms of the PRSUs. Upon a change of control, only those PRSUs that satisfy the relevant Tiptree share price target milestones from such a change of control transaction will vest, with all other PRSUs becoming forfeited unless otherwise assumed in such a change of control transaction. Neil Rifkind Mr. Rifkind’s employment was terminated by the Company without cause effective December 5, 2025 and he received a cash severance of $1,600,000. His 68,702 unvested RSUs remain outstanding and remain eligible for RSU Vesting.

  40. Principal Executive Officer Pay Ratio

    Principal Executive Officer Pay Ratio Set forth below is a reasonable estimate of the ratio of annual total compensation of the Company’s principal executive officer (“PEO”) to the median of the annual total compensation of all employees, other than the PEO. For 2025, the Company viewed Mr. Barnes, its Executive Chairman, and Mr. Ilany, its Chief Executive Officer (until December 31, 2025), collectively as the Company’s PEO. In 2025, we identified the median employee (such person, the “Median Employee”) by using as our consistently applied compensation measure, 2025 gross earnings, as reported on Form W-2 (“W-2 gross earnings”), for all individuals who were employed by the Company and its subsidiaries on December 31, 2025, other than our principal executive officers. We included all employees, whether employed on a full-time, part-time or seasonal basis, and we did not annualize the compensation of any full-time employee who was employed for less than the full 2025 calendar year. We believe that the use of W-2 gross earnings is an appropriate measure by which to determine the Median Employee because it accurately represents annual compensation earned by our employees. Messrs. Barnes and Ilany had 2025 annual total compensation of $8,215,284 and $10,278,460, respectively, as reflected in the Summary Compensation Table included in this Proxy Statement under “Executive Compensation— Summary Compensation”. Using the same methodology used to calculate Messrs. Barnes and Ilany’s 2025 total compensation in the Summary Compensation Table, our Median Employee’s total compensation for 2025 was $77,084. As a result, we estimate that Messrs. Barnes’s and Ilany’s 2025 annual total compensation was approximately 107 times and 133 times, respectively, that of our Median Employee. Because the SEC rules for identifying the median of the annual total compensation of our employees and calculating the pay ratio based on the employee’s annual total compensation allow companies to adopt a variety of methodologies, to apply certain exclusions, and to make reasonable estimates and assumptions that reflect their employee populations and compensation practices, the pay ratio reported by other companies may not be comparable to the pay ratio for the Company.

  41. Pay Versus Performance

    Pay Versus Performance

  42. Pay Versus Performance Table

    Pay Versus Performance Table 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 (as defined by SEC rules) and certain financial performance of the company. The CNG Committee did not consider the pay versus performance disclosure when making its incentive compensation decisions for any of the years presented. For further information about how we align executive compensation with the company’s performance, see “Compensation Discussion and Analysis” above. The amounts in the table below are calculated in accordance with SEC rules and do not represent amounts actually earned or realized by our NEOs, including with respect to stock options, RSUs and PRSUs.

  43. Pay Versus Performance Table

    | | | | | | Average Summary | Average | Value of Initial Fixed $100 Investment Based On: | | | | | | Summary Compensation Table Total for PEO(1) | | Compensation Actually Paid to PEO(1) | | Compensation Table Total | Compensation Actually Paid | Total | Peer Group Total | Net Income | Adjusted | | Year | Michael Barnes | Jonathan Ilany | Michael Barnes | Jonathan Ilany | for Non-PEO NEOs(2) | to Non-PEO NEOs(2) | Shareholder Return | Shareholder Return(3) | (Loss) (in thousands) | EBITDA(4) (in thousands) | | 2025 | $8,215,284 | $10,278,460 | $1,874,284 | $3,937,460 | $2,262,426 | $1,022,273 | 88.58 | 115.02 | $34,927 | $146,048 | | 2024 | $6,934,324 | $8,993,520 | $10,195,834 | $12,545,836 | $3,093,450 | $3,773,482 | 112.74 | 130.56 | $53,367 | $153,983 | | 2023 | $5,444,695 | $5,525,564 | $13,016,815 | $12,706,949 | $1,851,668 | $2,957,362 | 138.79 | 112.15 | $13,951 | $112,379 | | 2022 | $4,290,649 | $4,377,873 | $5,187,027 | $5,229,666 | $2,245,129 | $2,337,587 | 101.39 | 89.47 | $(8,274) | $81,124 | | 2021 | $8,877,686 | $9,168,916 | $20,046,694 | $15,143,999 | $1,760,133 | $2,781,169 | 279.68 | 135.04 | $38,132 | $100,776 |

  44. Pay Versus Performance Table

    (1) Prior to 2026, the Company considered the Executive Chairman and the Chief Executive Officer, as the Company’s Principal Executive Officer and therefore are presenting information for both Messrs. Barnes and Ilany separately for each of 2021 through 2025. Mr. Ilany ceased to be CEO effective December 31, 2025. (2) The Non-PEO NEOs in 2025 and 2024 consisted of Messrs. Maultsby, McKinney and Rifkind. Mr. Rifkind ceased to be a NEO effective December 5, 2025. The Non-PEO NEOs in 2023 consisted of Ms. Bell (until her retirement as our CFO on March 31, 2023) and Messrs. Maultsby, McKinney and Rifkind. In 2022 and 2021, the Non-PEO NEOs consisted of Ms. Bell and Messrs. Maultsby and Rifkind. (3) The Company used the same peer group, the Standard and Poor’s Select Sector Financial Services Index, as it used in the Stock Performance Graph for purposes of Item 201(e) of Regulation S-K. (4) We have identified Adjusted EBITDA as our company selected measure as we believe it represents the most important financial performance measures used to link compensation actually paid to our NEOs to company performance. For a reconciliation to Adjusted EBITDA from GAAP financials, see “Annex B: Non-GAAP Measures.” The additional tables below set forth each of the amounts required by SEC rules to be deducted from and added to the amount of total compensation as reflected in the Summary Compensation Table, to calculate compensation actually paid. The valuation assumptions used to calculate the fair values of stock options, RSUs and PRSUs did not materially differ from those used in our disclosures of fair value as of the grant date.

  45. Pay Versus Performance Table

    | Name | Year | Reported Summary Compensation Table Total for PEO | Minus: Reported Summary Compensation Table Value of Equity Awards | Plus: Equity Award Adjustments (1) | Compensation Actually Paid to PEO | | | 2025 | $8,215,284 | $(1,317,818) | $(5,023,182) | $1,874,284 | | | 2024 | $6,934,324 | $(5,753,000) | $9,014,510 | $10,195,834 | | Michael Barnes | 2023 | $5,444,695 | $— | $7,572,120 | $13,016,815 | | | 2022 | $4,290,649 | $— | $896,378 | $5,187,027 | | | 2021 | $8,877,686 | $(4,192,400) | $15,361,408 | $20,046,694 | | | 2025 | $10,278,460 | $(3,289,029) | $(3,051,971) | $3,937,460 | | | 2024 | $8,993,520 | $(5,753,000) | $9,305,315 | $12,545,836 | | Jonathan Ilany | 2023 | $5,525,564 | $— | $7,181,385 | $12,706,949 | | | 2022 | $4,377,873 | $— | $851,793 | $5,229,666 | | | 2021 | $9,168,916 | $(4,192,400) | $10,167,483 | $15,143,999 |

  46. Pay Versus Performance Table

    This table shows the equity award adjustments for the relevant year.

  47. Pay Versus Performance Table

    | Name | Year | Year End Fair Value of Awards Granted in the Year | Year over Year Change in Fair Value of Outstanding and Unvested Awards | Fair Value as of Vesting Date of Awards Granted and Vested in the Year | Year over Year Change in Fair Value of Awards Granted in Prior Years that Vested in the Year | Fair Value at the End of the Prior Year of Equity Awards That Have Been Forfeited During Year | Fair Value of Dividends Paid in Year Not Included in Total Compensation | Total Equity Award Adjustments | | | 2025 | $— | $(6,341,000) | $1,317,818 | $— | $— | $— | $(5,023,182) | | | 2024 | $6,391,000 | $2,220,930 | $— | $402,581 | $— | $— | $9,014,510 | | Michael | 2023 | $— | $7,306,360 | $— | $265,760 | $— | $— | $7,572,120 | | Barnes | 2022 | $— | $939,966 | $— | $(57,196) | $— | $13,609 | $896,378 | | | 2021 | $9,244,920 | $2,626,087 | $1,512,000 | $1,957,566 | $— | $20,835 | $15,361,408 | | | 2025 | $— | $(6,341,000) | $3,289,029 | $— | $— | $— | $(3,051,971) | | | 2024 | $6,391,000 | $2,220,930 | $— | $693,386 | $— | $— | $9,305,315 | | Jonathan | 2023 | $— | $7,181,385 | $— | $— | $— | $— | $7,181,385 | | Ilany | 2022 | $— | $831,380 | $— | $— | $— | $20,413 | $851,793 | | | 2021 | $9,244,920 | $— | $1,512,000 | $(620,689) | $— | $31,252 | $10,167,483 |

  48. Pay Versus Performance Table

    | Year | Reported Average Summary Compensation Table Total for Non-PEO NEOs | Minus: Reported Average Summary Compensation Table Value of Equity Awards | Plus: Average Equity Award Adjustments (1) | Average Compensation Actually Paid to Non- PEO NEOs | | 2025 | $2,262,426 | $(160,690) | $(1,079,463) | $1,022,273 | | 2024 | $3,093,450 | $(1,259,407) | $1,939,439 | $3,773,482 | | 2023 | $1,851,668 | $(157,706) | $1,263,400 | $2,957,362 | | 2022 | $2,245,129 | $(234,152) | $326,610 | $2,337,587 | | 2021 | $1,760,133 | $(465,822) | $1,486,858 | $2,781,169 |

  49. Pay Versus Performance Table

    This table shows the equity award adjustments for the relevant year.

  50. Pay Versus Performance Table

    | Year | Average Year End Fair Value of Awards Granted in the Year | Average Year over Year Change in Fair Value of Outstanding and Unvested Awards | Average Fair Value as of Vesting Date of Awards Granted and Vested in the Year | Average Year over Year Change in Fair Value of Awards Granted in Prior Years that Vested in the Year | Average Fair Value at the End of the Prior Year of Equity Awards That Have Been Forfeited During Year | Average Fair Value of Dividends Paid in Year Not Included in Total Compensation | Total Average Equity Award Adjustments | | 2025 | $— | $(1,246,017) | $160,690 | $(8,078) | $— | $13,942 | $(1,079,463) | | 2024 | $1,242,693 | $451,383 | $140,769 | $96,270 | $— | $8,324 | $1,939,439 | | 2023 | $71,621 | $1,067,428 | $94,622 | $24,378 | $— | $5,351 | $1,263,400 | | 2022 | $246,813 | $92,478 | $— | $(18,875) | $— | $6,193 | $326,610 | | 2021 | $1,027,214 | $281,042 | $167,998 | $3,759 | $— | $6,844 | $1,486,858 |

  51. Pay Versus Performance Table

    The following charts are intended to depict the relationship between (i) the compensation actually paid to our PEO EC (our Executive Chairman) and our PEO CEO (our CEO), as well as the average compensation actually paid to the other NEOs, and each of total shareholder return, net income, and Adjusted EBITDA.

  52. Key Performance Metrics Table

    | Most Important Company Performance Measures for Linking Compensation Actually Paid to Company Performance (For PEO & Other NEOs) | | • Adjusted EBITDA |