DEF 14A of Tiptree Inc., Mar 17, 2025

DEF 14A of Tiptree Inc.

Filed Mar 17, 2025 · FY20240001393726-25-000038

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 2024:

  2. Director Compensation Fiscal 2024

    Director Compensation Fiscal 2024

  3. Director Compensation Fiscal 2024

    | Name | Fees Earned or Paid in Cash ($) | Stock Awards ($)(1)(2) | Total ($) | | Michael G. Barnes(3) | — | — | — | | Paul M. Friedman | $120,000 | $123,048 | $243,048 | | Lesley Goldwasser | $100,000 | $147,684 | $247,684 | | Jonathan Ilany(3) | — | — | — | | Randy Maultsby(3) | — | — | — | | Dominique Mielle | $240,000 | $— | $240,000 | | Bradley E. Smith | $225,000 | $— | $225,000 |

  4. Director Compensation Fiscal 2024

    (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 4, 2024, July 8, 2024, October 7, 2024 and January 9, 2025 was $17.05, $16.33, $19.16, and $19.55, 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, 2024 in accordance with Accounting Standards Codification 718 — Compensation — Stock Compensation. See Note 19, Stock Based Compensation, to our consolidated financial statements in our 2024 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 and President, respectively, is included in the Summary Compensation Table below.

  5. Non-Employee Director Compensation Program

    Non-Employee Director Compensation Program In fiscal 2024, each non-employee director was eligible to receive an annual cash retainer of $112,500 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. Effective January 1, 2025, the annual cash retainer for non-employee directors was increased from $112,500 to $137,500 with all other terms described above remaining unchanged.

  6. CONTINUING DIRECTORS

    CONTINUING DIRECTORS The following table and biographical descriptions set forth certain information, as of March 17, 2025, with respect to each continuing director.

  7. CONTINUING DIRECTORS

    | Name | Age | Director Since | | Class I | | | | Paul M. Friedman (Chairman of the Audit Committee) | 69 | August 2016 | | Randy Maultsby | 51 | November 2021 | | Bradley E. Smith | 68 | July 2013 | | Class II | | | | Michael G. Barnes | 58 | August 2010 | | Dominique Mielle (Chair of the CNG Committee) | 56 | January 2020 |

  8. CONTINUING DIRECTORS

    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 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 also joined the board of Intelligo in 2020. 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 Inc. 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 Tiptree Financial Partners, L.P. (“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 Companies, Inc. (“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. 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. He is also the Company’s Executive Chairman and a member of the management executive committee. In 2007 Mr. Barnes founded 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.

  9. CONTINUING DIRECTORS

    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.

  10. 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 the 2026 annual meeting; 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 this Annual Meeting of stockholders. 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).

  11. 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 17, 2025, with respect to each nominee for election as director at the Annual Meeting. Mr. Ilany and Ms. Goldwasser 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.

  12. Information Regarding the Nominees for Election

    | Nominees for Election as Class III Directors | Age | Director Since | | Lesley Goldwasser (Lead Independent Director) | 63 | January 2015 | | Jonathan Ilany | 71 | August 2010 |

  13. Information Regarding the Nominees for Election

    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. 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 is our Chief Executive Officer and a member of our Executive Committee. He is also a member of our Board of Directors. 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.

  14. 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 | |

  15. 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 | | |

  16. 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 | | |

  17. 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 2024, our NEOs are listed in the table below, which shows the base salary and incentive compensation awarded to our NEOs for their performance in 2024 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 2024 in this CD&A we are referring to annual base salary paid in 2024, and cash bonuses for 2024 performance but paid in early 2025. 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 2024 were granted in such year but were based on 2023 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, Ilany, 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 19, Stock Based Compensation, to our consolidated financial statements in our 2024 Annual Report on Form 10-K.

  18. (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 ($) | | Michael G. Barnes Executive Chairman | 2024 | $1,100,000 | $— | $5,146,815 | — | $81,324 | $6,328,139 | | | 2023 | $1,000,000 | $4,382,697 | $— | — | $61,998 | $5,444,695 | | | 2022 | $1,000,000 | $3,227,466 | $— | — | $63,183 | $4,290,649 | | Jonathan Ilany Chief Executive Officer | 2024 | $1,100,000 | $2,001,319 | $7,179,979 | — | $139,201 | $10,420,499 | | | 2023 | $1,000,000 | $4,382,697 | $— | — | $142,867 | $5,525,564 | | | 2022 | $1,000,000 | $3,227,466 | $— | — | $150,407 | $4,377,873 | | Randy Maultsby President | 2024 | $500,000 | $1,750,000 | $1,274,006 | — | $10,725 | $3,534,731 | | | 2023 | $500,000 | $1,600,000 | $— | — | $9,326 | $2,109,326 | | | 2022 | $500,000 | $1,400,000 | $— | — | $7,644 | $1,907,644 | | Scott McKinney(3) Chief Financial Officer | 2024 | $500,000 | $1,250,000 | $1,047,500 | — | $10,725 | $2,808,225 | | | 2023 | $450,000 | $1,000,000 | $250,000 | — | $9,326 | $1,709,326 | | Neil C. Rifkind(3) VP, General Counsel and Secretary | 2024 | $500,000 | $880,000 | $440,000 | — | $100,679 | $1,920,679 | | | 2023 | $500,000 | $800,000 | $400,000 | — | $71,618 | $1,771,618 | | | 2022 | $450,000 | $720,000 | $360,000 | — | $7,644 | $1,537,644 |

  19. (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 Mr. Maultsby for 2024, 2023 and 2022, Mr. McKinney for 2024 and 2023 and Mr. Rifkind for 2022, this represents premiums paid by the Company to our group health insurance provider under a medical expenses reimbursement plan (the “MERP”). 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. Barnes’s $63,183 of other compensation in 2022 consists of $7,644 attributable to the MERP, $28,361 attributable to travel reimbursements and $27,178 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. Ilany’s $150,407 of other compensation in 2022 consists of $7,644 attributable to the MERP, $53,761 attributable to travel reimbursements, $19,726 that the Company paid in connection with maintaining the IT infrastructure in Mr. Ilany’s home office and $69,276 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 and Mr. Rifkind’s stock award amounts for performance years 2024, 2023 and 2022 represent the Par Value of the RSU issuances on February 25, 2025, February 27, 2024 and February 22, 2023, 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.

  20. Use of Independent Compensation Consultant

    Use of Independent Compensation Consultant The CNG Committee engaged CAP to serve as its independent compensation consultant during 2024. 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 2024 with respect to compensation decisions for 2024 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 2024, 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 2024, 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.

  21. 2024 Compensation Highlights

    2024 Compensation Highlights Compensation of our NEOs is largely driven by the financial and strategic performance of the Company. Total compensation of our NEOs related to fiscal 2024 was approximately $25 million compared to $16.5 million in fiscal 2023, with the increase year over year driven largely by the grant date fair value of the grants of PRSUs with a $70 share price target (adjusted for dividends) as the vesting criteria for such awards. In approving the compensation program for 2024, the CNG Committee considered a number of factors including, but not limited to the responsibilities of the executives’ positions, the executives’ experience and contributions, the competitive marketplace for executive talent and corporate performance. Consistent with Tiptree’s pay for performance philosophy, NEO pay mix is heavily weighted toward variable, performance-based pay, which ties a large portion of compensation to the achievement of our short- and long-term performance objectives. The charts below illustrate the fixed versus variable mix of compensation for our NEOs in 2024. As seen in the illustration below, for 2024, only 15% of compensation was fixed for the Executive Committee while 85% was variable, which we define as compensation in the form of any cash or stock award subject to forfeiture (including RSUs and PRSUs). 17% of the compensation of the other current NEOs at year-end was fixed while 83% was variable. Fixed compensation consists of base salary and other guaranteed reimbursements such as travel and information technology reimbursements and related tax gross-ups and the premiums paid for executives under our medical expense reimbursement plan, or MERP. Variable compensation consists of any award based on performance and CNG Committee determination (including negative discretion).

  22. 2024 Executive Compensation Program and Decisions

    | Name | Annual Cash Incentive Award | | Michael Barnes | $0 | | Jonathan Ilany | $2,001,319 | | Total | $2,001,319 |

  23. 2024 Executive Compensation Program and Decisions

    | Name | Annual Cash Incentive Award | | Randy Maultsby | $1,750,000 | | Scott McKinney | $1,250,000 | | Neil Rifkind | $880,000 | | Total | $3,880,000 |

  24. Summary Compensation Table

    Summary Compensation Table

  25. Summary Compensation Table

    | Name and Title | Year | Salary($) | Bonus ($) | Stock Awards ($)(1) | Option Awards ($)(1) | Non-Equity Incentive Plan Compensation(2) | All Other Compensation ($)(3) | Total ($) | | Michael G. Barnes(4) Executive Chairman | 2024 | $1,100,000 | — | $5,753,000 | — | $— | $81,324 | $6,934,324 | | | 2023 | $1,000,000 | — | $— | — | $4,382,697 | $61,998 | $5,444,695 | | | 2022 | $1,000,000 | — | $— | — | $3,227,466 | $63,183 | $4,290,649 | | Jonathan Ilany(5) Chief Executive Officer | 2024 | $1,100,000 | — | $5,753,000 | — | $2,001,319 | $139,201 | $8,993,520 | | | 2023 | $1,000,000 | — | $— | — | $4,382,697 | $142,867 | $5,525,564 | | | 2022 | $1,000,000 | — | $— | — | $3,227,466 | $150,407 | $4,377,873 | | Randy Maultsby(6) President | 2024 | $500,000 | — | $1,917,663 | — | $1,750,000 | $10,725 | $4,178,388 | | | 2023 | $500,000 | — | $— | — | $1,600,000 | $9,326 | $2,109,326 | | | 2022 | $500,000 | — | $— | — | $1,400,000 | $7,644 | $1,907,644 | | Scott McKinney(7) Chief Financial Officer | 2024 | $500,000 | — | $1,438,250 | — | $1,250,000 | $10,725 | $3,198,975 | | | 2023 | $450,000 | — | $252,337 | — | $1,000,000 | $9,326 | $1,711,663 | | Neil C. Rifkind(8) 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 | | | 2022 | $450,000 | — | $351,228 | — | $720,000 | $7,644 | $1,528,872 |

  26. Summary Compensation Table

    (1)Amounts in this column represent the aggregate grant date fair value of PRSUs, 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 19, Stock Based Compensation, to our consolidated financial statements in our 2024 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. (3)For Mr. Maultsby for 2024, 2023 and 2022, Mr. McKinney for 2024 and 2023 and Mr. Rifkind for 2022, this represents premiums paid by the Company to our group health insurance provider under a medical expenses reimbursement plan (the “MERP”). 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. Barnes’s $63,183 of other compensation in 2022 consists of $7,644 attributable to the MERP, $28,361 attributable to travel reimbursements and $27,178 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. Ilany’s $150,407 of other compensation in 2022 consists of $7,644 attributable to the MERP, $53,761 attributable to travel reimbursements, $19,726 that the Company paid in connection with maintaining the IT infrastructure in Mr. Ilany’s home office and $69,276 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. (4)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 amount in 2024, 2023 and 2022 represents the grant date fair value of RSUs granted to him on February 27, 2024, February 22, 2023 and February 17, 2022, respectively.

  27. 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, 2024:

  28. Grants of Plan-Based Awards

    | | Estimated Future Payouts Under Non-Equity Incentive Plan Awards(1) | | | | | | | Name | Threshold | Target | Maximum | Grant Date | All Other Stock Awards: Number of Shares of Stock or Units(2) | Grant Date Fair Value(3) ($) | | Michael G. Barnes | — | $— | — | 1/1/2024 | 550,000 | $— | | Jonathan Ilany | — | $2,001,319 | — | 1/1/2024 | 550,000 | $— | | Randy Maultsby | — | — | — | 1/1/2024 | 183,333 | $— | | Scott McKinney | — | — | — | 1/1/2024 | 137,500 | | | Neil C. Rifkind | — | — | — | 2/27/2024 | 23,792 | $422,308 |

  29. Grants of Plan-Based Awards

    ________________________________ (1)For Messrs. Barnes and Ilany, the dollar figures in the table above represent the incentive compensation pool for the Executive Committee based on a percentage of 2024 Adjusted EBITDA which was paid in the first quarter of 2025. The actual amounts granted to Messrs. Maultsby, McKinney and Rifkind were subject to the discretion of the Executive Committee and, as such, do not have calculable threshold, target or maximum estimated payouts. (2)On January 1 2024, Messrs. Barnes, Ilany, Maultsby and McKinney were granted PRSUs which shall vest upon achievement of a $70 Tiptree share price target milestone (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, generally subject to the grantee’s continued employment with Tiptree. Mr. Rifkind was granted matching RSUs on February 27, 2024, which will cliff vest on February 20, 2027, subject to certain terms contained in the award agreements. (3)The grant date 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, please see Note 19, Stock Based Compensation, to our consolidated financial statements in our 2024 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. The grant date fair value of RSUs is computed in accordance with FASB ASC Topic 718. RSUs are valued using the closing price of our common stock on the grant date ($17.75 per share). Pursuant to SEC rules, the amounts shown exclude the impact of estimated forfeitures related to service-based vesting conditions. 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 — Executive Chairman 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 ($1,100,000 for 2024) 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. Jonathan Ilany — Chief Executive Officer Under Mr. Ilany’s Executive Employment Agreement dated as of February 1, 2018, Mr. Ilany receives compensation for serving as Chief Executive Officer of Tiptree consisting of an annual base salary ($1,100,000 for 2024) and a discretionary annual cash bonus in an amount set by the CNG Committee. Mr. Ilany 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. Randy Maultsby — President Under Mr. Maultsby’s Executive Employment Agreement dated as of July 14, 2021, Mr. Maultsby receives an annual base salary ($500,000 for 2024) 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 2024) 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 — Vice President, General Counsel and Secretary Under Mr. Rifkind’s Executive Employment Agreement dated as of February 1, 2018, Mr. Rifkind receives an annual base salary ($500,000 for 2024) and a discretionary annual cash bonus in an amount set by the CNG Committee. Mr. Rifkind 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.

  30. 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, 2024. As described more fully in footnote 1 below, the stock options are subject to time based vesting with respect to one-third of the shares subject to the award on each of the third, fourth and fifth anniversaries of the date of grant and a performance based vesting requirement that has been achieved. 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.

  31. 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) | | Michael G. Barnes | | 1/4/2016 | 46,494 | — | $5.67 | 1/4/2026 | | | 1,750,000 | $8,906,480 | | | | 3/10/2016 | 4,649 | — | $5.87 | 3/10/2026 | | | | | | | | 2/22/2017 | 112,015 | — | $6.65 | 2/22/2027 | | | | | | | | 2/26/2018 | 93,332 | — | $5.85 | 2/26/2028 | | | | | | | | 2/26/2019 | 90,326 | | $6.26 | 2/26/2029 | | | | | | | | 2/20/2020 | 113,408 | 56,703 | $7.25 | 2/20/2030 | | | | | | Jonathan Ilany | | 1/4/2016 | 137,038 | — | $5.67 | 1/4/2026 | | | 1,750,000 | $8,906,480 | | | | 3/10/2016 | 13,704 | — | $5.87 | 3/10/2026 | | | | | | | | 2/22/2017 | 351,155 | — | $6.65 | 2/22/2027 | | | | | | | | 2/26/2018 | 149,331 | — | $5.85 | 2/26/2028 | | | | | | | | 2/26/2019 | 135,489 | | $6.26 | 2/26/2029 | | | | | | | | 2/20/2020 | 170,111 | 85,055 | $7.25 | 2/20/2030 | | | | | | Randy Maultsby | | | — | — | — | — | — | $— | 583,333 | $2,968,823 | | Scott McKinney | | | — | — | — | — | 30,846(5) | $643,448 | 437,500 | $2,226,620 | | Neil C. Rifkind | | | — | — | — | — | 73,206(6) | $1,527,077 | — | $— |

  32. Outstanding Equity Awards at Fiscal Year-End

    (1)All outstanding and unexercised stock options have met their performance-based vesting requirements and remain subject to the time-based vesting requirements before becoming exercisable. For Mr. Barnes, the unexercised options consist of 56,703 Stock Options granted on February 20, 2020 which will become exercisable on February 26, 2025. For Mr. Ilany, the unexercised options consist of 85,055 Stock Options granted on February 20, 2020 which will become exercisable on February 26, 2025. The Stock Options will expire on the earlier of (1) the ten-year anniversary of the grant date of the Stock Option and (2) the date of the termination of Mr. Barnes’s (with respect to Mr. Barnes’s Stock Options) or Mr. Ilany’s (with respect to Mr. Ilany’s Stock Option) service with the Company for cause (as defined in the Stock Option Agreement) or their respective voluntary termination of service with the Company (other than a termination of employment for good reason (as defined in the Employment Agreement) or for retirement (as defined below under “—Potential Payments to Named Executive Officers Upon Termination or Change in Control”). (2)Based on the common stock closing price on the date such options are granted. (3)Based on the common stock closing price of $20.86 on December 31, 2024 (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 19, Stock Based Compensation, to our consolidated financial statements in our 2024 Annual Report on Form 10-K. (5)Mr. McKinney’s 30,846 unvested RSUs consist of (a) 15,736 RSUs granted to him on February 17, 2022, which cliff vested on February 20, 2025 and (b) 15,110 RSUs granted to him on February 22, 2023, which will cliff vest on February 20, 2026, in each case generally subject to Mr. McKinney’s continued employment with Tiptree. (6)Mr. Rifkind’s 73,206 unvested RSUs consist of (a) 26,750 RSUs granted to him on February 17, 2022, which cliff vested on February 20, 2025, (b) 22,664 RSUs granted to him on February 22, 2023, which will cliff vest on February 20, 2026 and (c) 23,792 RSUs granted to him on February 27, 2024, which will cliff vest on February 20, 2027, in each case generally subject to Mr. Rifkind’s continued employment with Tiptree.

  33. Option Exercises and Stock Vested

    Option Exercises and Stock Vested None of our NEOs had any RSUs vest in 2024 and no stock options were exercised by our NEOs during 2024.

  34. 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 Messrs. Barnes and Ilany, (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, 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. All of our currently employed NEOs, other than Messrs. Maultsby and McKinney, qualify 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, 2024, he would have been entitled to receive a total severance of $6,582,697, 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, 2024: ◦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. Jonathan Ilany •If Mr. Ilany’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, 2024, he would have been entitled to receive a total severance of $8,584,016, 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. Ilany’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. Ilany’s stock options will be exercisable, given their performance requirements have been achieved. •With respect to Mr. Ilany’s 1,750,000 unvested PRSUs as of December 31, 2024: ◦If Mr. Ilany’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, 2024, he would have been entitled to receive a total severance of $2,250,000, which represents his base salary and incentive compensation for services performed in 2024. •With respect to Maultsby’s 583,333 unvested PRSUs as of December 31, 2024: ◦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. ◦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, 2024, 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 2024.

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

    •If Mr. McKinney’s employment was terminated by the Company due to his death or disability, then his 30,846 unvested RSUs as of December 31, 2024, with a market value of $643,448 based on the Company’s closing stock price of $20.86 as of December 31, 2024 would vest immediately upon termination. •If Mr. McKinney’s employment was terminated by the Company without cause, then his 30,846 unvested RSUs as of December 31, 2024 would remain outstanding and vest in accordance with their vesting schedule (the “RSU Vesting”). •Upon a change of control, Mr. McKinney’s 30,846 unvested RSUs as of December 31, 2024, with a market value of $643,448 based on the Company’s closing stock price of $20.86 as of December 31, 2024, would become fully vested. •With respect to McKinney’s 437,500 unvested PRSUs as of December 31, 2024: ◦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 •If Mr. Rifkind’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, 2024, he would have been entitled to receive a total severance of $1,820,000, which represents his base salary and incentive compensation for services performed in 2024. •If Mr. Rifkind’s employment was terminated by the Company due to his death or disability, then his 73,206 unvested RSUs, with a market value of $1,527,077 based on the Company’s closing stock price of $20.86 as of December 31, 2024, would vest immediately upon termination. •If Mr. Rifkind’s employment was terminated by the Company without cause or as a result of his retirement, then his 73,206 unvested RSUs as of December 31, 2024 would remain outstanding and remain eligible for RSU Vesting. •Upon a change of control, Mr. Rifkind’s 73,206 unvested RSUs as of December 31, 2024, with a market value of $1,527,077 based on the Company’s closing stock price of $20.86 as of December 31, 2024, would become fully vested.

  36. 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. The Company views the Executive Committee, consisting of Mr. Barnes, its Executive Chairman, and Mr. Ilany, its Chief Executive Officer, collectively as the Company’s PEO. In 2024, we identified the median employee (such person, the “Median Employee”) by using as our consistently applied compensation measure, 2024 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, 2024, 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 2024 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 2024 annual total compensation of $6,934,324 and $8,993,520, 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 2024 total compensation in the Summary Compensation Table, our Median Employee’s total compensation for 2024 was $100,476. As a result, we estimate that Messrs. Barnes’s and Ilany’s 2024 annual total compensation was approximately 69 times and 89 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.

  37. Pay Versus Performance

    Pay Versus Performance

  38. 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.

  39. Pay Versus Performance Table

    | | | | | | | | Value of Initial Fixed $100 Investment Based On: | | | | | Year | Summary Compensation Table Total for PEO(1) | | Compensation Actually Paid to PEO(1) | | Average Summary Compensation Table Total for Non-PEO NEOs(2) | Average Compensation Actually Paid to Non-PEO NEOs(2) | Total Shareholder Return | Peer Group Total Shareholder Return(3) | Net Income (Loss) (in thousands) | Adjusted EBITDA(4) (in thousands) | | | Michael Barnes | Jonathan Ilany | Michael Barnes | Jonathan Ilany | | | | | | | | 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 | | 2020 | $1,853,328 | $2,579,448 | $405,023 | $575,685 | $1,123,673 | $808,850 | 63.56 | 98.31 | $(29,158) | $4,541 |

  40. Pay Versus Performance Table

    ___________________________________ (1) The Company considers its executive committee, consisting of the Executive Chairman and 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 2020 through 2024. (2) The Non-PEO NEOs in 2024 consisted of Messrs. Maultsby, McKinney and Rifkind. 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. The Non-PEO NEOs in 2020 consisted of Ms. Bell and Mr. Rifkind only. For 2022, this includes a one-time severance payment to Ms. Bell of $1,470,000. (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 GAAP financials, see “Annex A: 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.

  41. 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 | | Michael Barnes | 2024 | $6,934,324 | $(5,753,000) | $9,014,510 | $10,195,834 | | | 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 | | | 2020 | $1,853,328 | $(927,986) | $(520,319) | $405,023 | | Jonathan Ilany | 2024 | $8,993,520 | $(5,753,000) | $9,305,315 | $12,545,836 | | | 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 | | | 2020 | $2,579,448 | $(1,391,982) | $(611,781) | $575,685 |

  42. Pay Versus Performance Table

    (1) This table shows the equity award adjustments for the relevant year.

  43. 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 | | Michael Barnes | 2024 | $6,391,000 | $2,220,930 | $— | $402,581 | $— | $— | $9,014,510 | | | 2023 | $— | $7,306,360 | $— | $265,760 | $— | $— | $7,572,120 | | | 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 | | | 2020 | $539,132 | $(834,881) | $— | $(252,872) | $— | $28,301 | $(520,319) | | Jonathan Ilany | 2024 | $6,391,000 | $2,220,930 | $— | $693,386 | $— | $— | $9,305,315 | | | 2023 | $— | $7,181,385 | $— | $— | $— | $— | $7,181,385 | | | 2022 | $— | $831,380 | $— | $— | $— | $20,413 | $851,793 | | | 2021 | $9,244,920 | $— | $1,512,000 | $(620,689) | $— | $31,252 | $10,167,483 | | | 2020 | $168,234 | $— | $640,467 | $(1,463,680) | $— | $43,199 | $(611,781) |

  44. 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 | | 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 | | 2020 | $1,123,673 | $(116,029) | $(198,794) | $808,850 |

  45. Pay Versus Performance Table

    (1) This table shows the equity award adjustments for the relevant year.

  46. 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 | | 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 | | 2020 | $80,340 | $(56,491) | $— | $(230,867) | $— | $8,223 | $(198,794) |

  47. 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.

  48. Key Performance Metrics Table

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