DEF 14A of Tiptree Inc., Mar 18, 2024

DEF 14A of Tiptree Inc.

Filed Mar 18, 2024 · FY20230001393726-24-000046

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 2023:

  2. Director Compensation Fiscal 2023

    Director Compensation Fiscal 2023

  3. Director Compensation Fiscal 2023

    | Name | Fees Earned or Paid in Cash ($) | Stock Awards ($)(1)(2) | Total ($) | | Michael G. Barnes(3) | — | — | — | | Paul M. Friedman | $90,000 | $124,120 | $214,120 | | Lesley Goldwasser | $95,000 | $124,120 | $219,120 | | Jonathan Ilany(3) | — | — | — | | Randy Maultsby(3) | — | — | — | | Dominique Mielle | $85,000 | $124,120 | $209,120 | | Bradley E. Smith | $162,500 | $37,069 | $199,569 |

  4. Director Compensation Fiscal 2023

    (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 6, 2023, July 6, 2023, October 6, 2023 and January 4, 2024 was $14.02, $15.06, $15.90, and $18.78, 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, 2023 in accordance with Accounting Standards Codification 718 — Compensation — Stock Compensation. See Note 19, Stock Based Compensation, to our consolidated financial statements in our 2023 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 2023, each non-employee director was eligible to receive an annual cash retainer of $100,000 plus $100,000 in immediately vested shares of our common stock, both of which are paid quarterly in arrears. Such non-employee directors may elect to receive up to $125,000 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 $20,000, the Chair of the Audit Committee received an additional annual retainer of $15,000 and the Chair of the CNG Committee received an additional annual retainer of $10,000. 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 18, 2024, with respect to each continuing director.

  7. CONTINUING DIRECTORS

    | Name | Age | Director Since | | Class I | | | | Paul M. Friedman (Chairman of the Audit Committee) | 68 | August 2016 | | Randy Maultsby | 50 | November 2021 | | Bradley E. Smith | 67 | July 2013 | | Class III | | | | Lesley Goldwasser (Lead Independent Director) | 62 | January 2015 | | Jonathan Ilany | 70 | August 2010 |

  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 Great Ajax Corp., where he is a member of both the audit and compensation committees. 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 is a member of the Board of Directors of Invesque Inc., where he also serves 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”) 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. 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 FinTech Acquisition Corp. V., and joined the board of FTAC Parnassus Acquisition Corp. in March 2021. 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 1996 until 2000, Mr. Ilany was a private investor. From 1982 until 1995, 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 the 2026 annual meeting; Class II, consisting of Michael G. Barnes and Dominique Mielle, to hold office for a term expiring at this Annual Meeting of stockholders; and Class III, consisting of Jonathan Ilany and Lesley Goldwasser, to hold office for a term expiring at the 2025 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 18, 2024, with respect to each nominee for election as director at the Annual Meeting. Mr. Barnes and Ms. Mielle 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 II Directors | Age | Director Since | | Michael G. Barnes | 57 | August 2010 | | Dominique Mielle (Chair of the CNG Committee) | 55 | January 2020 |

  12. Information Regarding the Nominees for Election

    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 Tiptree Financial Partners, L.P. (“TFP”), Tiptree’s predecessor, 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 Corvid Peak Holdings, L.P., formerly known as Tricadia Holdings, L.P., and its affiliated companies. Prior to the formation of Corvid Peak 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”), where she worked 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. Ms. Mielle was a director of PG&E Corporation and Pacific Gas and Electric Company from April 2019 until June 2020, where she served as the chair of the audit committee. She was a director of Anworth Mortgage Asset Corporation, a mortgage REIT investment firm, where she served as the chair of the compensation committee and served on the audit and compensation, nominating and corporate governance committees from 2018 until its merger with Ready Capital Corp. in March 2021. In connection with the merger, Ms. Mielle became a director of Ready Capital Corp. Ms. Mielle also has been 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. She is also a director of Osiris Acquisition Corp. since May 2021, where she is the chair of their audit committee. She was a director of Digicel Group from July 2020 to February 2023. 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.

  13. 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 For performance years 2022 and 2023, only RSUs were granted given the PRSUs granted in 2021 were intended to cover three years of long-term incentive awards. | | | Restricted stock units (“RSUs”) subject to time-based vesting | Time-based vesting encourages retention; potential increased value achieved through stock appreciation | |

  14. 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 | | |

  15. 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 | | |

  16. 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 2023, our NEOs are listed in the table below, which shows the base salary and incentive compensation awarded to our NEOs for their performance in 2023 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 2023 in this CD&A we are referring to annual base salary paid in 2023, and cash bonuses for 2023 performance but paid in early 2024. 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 2023 were granted in such year but were based on 2022 performance. On August 4, 2021, the Company granted Messrs. Barnes, Ilany and Maultsby an aggregate of 3,500,000 PRSUs, which are intended to cover three years of long-term incentive awards. Messrs. Barnes, Ilany and Maultsby will not receive another award under the long-term incentive program until 2024. 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 and stock option awards, please see Note 19, Stock Based Compensation, to our consolidated financial statements in our 2023 Annual Report on Form 10-K.

  17. (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 | 2023 | $1,000,000 | $4,382,697 | $— | — | $61,998 | $5,444,695 | | | 2022 | $1,000,000 | $3,227,466 | $— | — | $63,183 | $4,290,649 | | | 2021 | $600,000 | $4,057,703 | $1,512,000 | — | $27,583 | $6,197,286 | | Jonathan Ilany Chief Executive Officer | 2023 | $1,000,000 | $4,382,697 | $— | — | $142,867 | $5,525,564 | | | 2022 | $1,000,000 | $3,227,466 | $— | — | $150,407 | $4,377,873 | | | 2021 | $800,000 | $4,057,703 | $1,512,000 | — | $118,813 | $6,488,516 | | Randy Maultsby(3) President | 2023 | $500,000 | $1,600,000 | $— | — | $9,326 | $2,109,326 | | | 2022 | $500,000 | $1,400,000 | $— | — | $7,644 | $1,907,644 | | | 2021 | $350,000 | $1,250,000 | $503,995 | — | $7,644 | $2,111,639 | | Sandra Bell(4) Former Chief Financial Officer | 2023 | $112,500 | $— | $— | — | $1,723,077 | $1,835,577 | | | 2022 | $450,000 | $1,020,000 | $— | | $— | $1,470,000 | | | 2021 | $450,000 | $680,000 | $340,000 | — | $7,644 | $1,477,644 | | Scott McKinney(5) Chief Financial Officer | 2023 | $450,000 | $1,000,000 | $252,337 | — | $9,326 | $1,711,663 | | Neil C. Rifkind(6) VP, General Counsel and Secretary | 2023 | $500,000 | $800,000 | $400,000 | — | $71,618 | $1,771,618 | | | 2022 | $450,000 | $720,000 | $360,000 | — | $7,644 | $1,537,644 | | | 2021 | $450,000 | $680,000 | $340,000 | — | $7,644 | $1,477,644 |

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

    (1)For Messrs. Barnes, Ilany and Maultsby in performance year 2021, this represents 100,000, 100,000 and 33,333 shares, respectively, issued on November 22, 2021 pursuant to vested PRSUs (the $15 target), with a closing stock price of $15.12. For Ms. Bell and Mr. Rifkind, this represents the Par Value of RSU grants. (2)For Ms. Bell for 2021, Mr. McKinney for 2023, Mr. Rifkind for 2022 and 2021 and for Mr. Maultsby for 2023, 2022 and 2021, this represents premiums paid by the Company to our group health insurance provider under a medical expenses reimbursement plan (the “MERP”). 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. Barnes’s $27,583 of other compensation in 2021 consists of $7,644 attributable to the MERP, $10,169 attributable to travel reimbursements and $9,770 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. Ilany’s $118,813 of other compensation in 2021 consists of $7,644 attributable to the MERP, $41,197 attributable to travel reimbursements, $15,499 that the Company paid in connection with maintaining the IT infrastructure in Mr. Ilany’s home office and $54,473 of reimbursements for taxes associated with such reimbursements. Ms. Bell’s $1,723,077 of other compensation in 2023 consists of $9,326 attributable to the MERP and $1,470,000 of severance and $243,750 of compensation for services provided to the Company from April 1, 2023 to October 15, 2023, pursuant to the Transition Agreement, all of which were paid in calendar year 2023. 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. Maultsby was appointed our President on July 14, 2021. (4)Ms. Bell’s stock award amounts for performance year 2021 represent the Par Value of the RSU issuances on February 17, 2022 in which Ms. Bell 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 issuance for 2021 was doubled accordingly. Pursuant to the Transition Agreement, Ms. Bell retired as Chief Financial Officer of the Company effective March 31, 2023 and remained employed to assist with special projects until October 15, 2023. Her salary column reflects her salary from January 1, 2023 to March 31, 2023. The remainder of her compensation paid in 2023 are reflected in the “Other Compensation” column. (5)Mr. McKinney’s stock award amount in 2023 represents the grant date fair value of RSUs granted to him on February 22, 2023. (6)Mr. Rifkind’s stock award amounts for performance years 2023, 2022 and 2021 represent the Par Value of the RSU issuances on February 27, 2024, February 22, 2023 and February 17, 2022, respectively, in which Mr. Rifkind 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.

  19. Use of Independent Compensation Consultant

    Use of Independent Compensation Consultant The CNG Committee engaged CAP to serve as its independent compensation consultant during 2023. 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 2023 with respect to compensation decisions for 2023 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 2023, 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 2023, 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.

  20. 2023 Executive Compensation Program and Decisions

    | Name | Annual Cash Incentive Award | | Michael Barnes | $4,382,697 | | Jonathan Ilany | $4,382,697 | | Total | $8,765,394 |

  21. 2023 Executive Compensation Program and Decisions

    | Name | Annual Cash Incentive Award | | Randy Maultsby | $1,600,000 | | Sandra Bell(1) | $— | | Scott McKinney | $1,000,000 | | Neil Rifkind | $800,000 | | Total | $3,400,000 |

  22. Summary Compensation

    Summary Compensation The following table sets forth information regarding the compensation paid to or earned by our NEOs for services in 2023, 2022 and 2021, as applicable to each NEO, in the format required by the SEC. The footnotes to these tables provide information to explain the values presented in the tables and are an important part of our disclosures. We have included a separate table in “Compensation Discussion and Analysis—Named Executive Officers” as supplemental disclosure, which table shows the base salary and incentive compensation awarded to our NEOs for their performance in 2023, 2022 and 2021, as applicable to each NEO, in the manner that it was considered by the CNG Committee. Except where otherwise noted, the equity awards shown in our Summary Compensation Table and Grants of Plan-Based Awards table for the years 2023 and 2022 were granted in February 2023 and 2022, respectively, for services performed in 2022 and 2021, respectively. Our CNG Committee did not grant any equity awards in 2021 for services performed in 2020. The only equity awards granted in 2021 were the PRSUs granted to our Executive Chairman, Chief Executive Officer and President, which reflect the CNG Committee’s desire for such executives to continue to lead Tiptree for an additional significant number of years and to create significant shareholder value over time.

  23. Summary Compensation Table

    Summary Compensation Table

  24. 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 | 2023 | $1,000,000 | — | $— | $— | $4,382,697 | $61,998 | $5,444,695 | | | 2022 | $1,000,000 | — | $— | $— | $3,227,466 | $63,183 | $4,290,649 | | | 2021 | $600,000 | — | $4,192,400 | $— | $4,057,703 | $27,583 | $8,877,686 | | Jonathan Ilany(5) Chief Executive Officer | 2023 | $1,000,000 | — | $— | $— | $4,382,697 | $142,867 | $5,525,564 | | | 2022 | $1,000,000 | — | $— | $— | $3,227,466 | $150,407 | $4,377,873 | | | 2021 | $800,000 | — | $4,192,400 | $— | $4,057,703 | $118,813 | $9,168,916 | | Randy Maultsby(6) President | 2023 | $500,000 | — | $— | — | $1,600,000 | $9,326 | $2,109,326 | | | 2022 | $500,000 | — | $— | — | $1,400,000 | $7,644 | $1,907,644 | | | 2021 | $350,000 | — | $1,397,466 | — | $1,250,000 | $7,644 | $3,005,110 | | Sandra Bell(7) Former Chief Financial Officer | 2023 | $112,500 | — | $— | — | $— | $1,723,077 | $1,835,577 | | | 2022 | $450,000 | — | $351,228 | — | $1,020,000 | $— | $1,821,228 | | | 2021 | $450,000 | — | $— | — | $680,000 | $7,644 | $1,137,644 | | Scott McKinney(8) Chief Financial Officer | 2023 | $450,000 | — | $252,337 | — | $1,000,000 | $9,326 | $1,711,663 | | Neil C. Rifkind(9) VP, General Counsel and Secretary | 2023 | $500,000 | — | $378,489 | — | $800,000 | $71,618 | $1,750,107 | | | 2022 | $450,000 | — | $351,228 | — | $720,000 | $7,644 | $1,528,872 | | | 2021 | $450,000 | — | $— | — | $680,000 | $7,644 | $1,137,644 |

  25. Summary Compensation Table

    (1)Amounts in this column represent the aggregate grant date fair value of PRSUs, RSUs and stock options, computed in accordance with FASB ASC Topic 718. RSUs are valued using the closing price of our common stock on the grant date. We use the Black-Scholes model assuming 50% volatility to estimate our compensation cost for stock option awards. 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 2023 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 Ms. Bell for 2021, Mr. McKinney for 2023, Mr. Rifkind for 2022 and 2021 and for Mr. Maultsby for 2023, 2022 and 2021, this represents premiums paid by the Company to our group health insurance provider under a medical expenses reimbursement plan (the “MERP”). 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. Barnes’s $27,583 of other compensation in 2021 consists of $7,644 attributable to the MERP, $10,169 attributable to travel reimbursements and $9,770 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. Ilany’s $118,813 of other compensation in 2021 consists of $7,644 attributable to the MERP, $41,197 attributable to travel reimbursements, $15,499 that the Company paid in connection with maintaining the IT infrastructure in Mr. Ilany’s home office and $54,473 of reimbursements for taxes associated with such reimbursements. Ms. Bell’s $1,723,077 of other compensation in 2023 consists of $9,326 attributable to the MERP and $1,470,000 of severance and $243,750 of compensation for services provided to the Company from April 1, 2023 to October 15, 2023, pursuant to the Transition Agreement, all of which were paid in calendar year 2023. 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 2021 represents the 1,500,000 PRSUs granted on August 4, 2021. (5)Mr. Ilany’s stock award amount in 2021 represents the 1,500,000 PRSUs granted on August 4, 2021. (6)Mr. Maultsby’s stock award amount in 2021 represents the 500,000 PRSUs granted to him on August 4, 2021. (7)Pursuant to the Transition Agreement, Ms. Bell retired as Chief Financial Officer of the Company effective March 31, 2023 and remained employed to assist with special projects until October 15, 2023. Her salary column reflects her salary from January 1, 2023 to March 31, 2023. The remainder of her compensation amounts paid in 2023 is reflected in the “Other Compensation” column. Ms. Bell’s stock award amount in 2022 represents the grant date fair value of RSUs granted to her on February 17, 2022. (8)Mr. McKinney’s stock award amount in 2023 represents the grant date fair value of RSUs granted to him on February 22, 2023. (9)Mr. Rifkind’s stock award amount in 2023 and 2022 represents the grant date fair value of RSUs granted to him on February 22, 2023 and February 17, 2022, respectively.

  26. 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, 2023:

  27. 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 | — | $4,382,697 | — | — | — | $— | | Jonathan Ilany | — | $4,382,697 | — | — | — | $— | | Randy Maultsby | — | — | — | — | — | $— | | Sandra Bell | — | — | — | — | — | $— | | Scott McKinney | — | — | — | 2/22/2023 | 15,110 | $252,337 | | Neil C. Rifkind | — | — | — | 2/22/2023 | 22,664 | $378,489 |

  28. 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 2023 Adjusted EBITDA which was paid in the first quarter of 2024. The aggregate incentive compensation pool for our 2023 named executive officers other than the Executive Committee (Messrs. Maultsby, McKinney and Rifkind), is subject to a cap of 4.5% of Adjusted EBITDA prior to the payment of the incentive compensation of the Executive Committee. 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)In 2023, the only stock awards granted to NEOs were RSUs granted to Messrs. McKinney and Rifkind on February 22, 2023, which will cliff vest on February 20, 2026, subject to certain terms contained in the award agreements. (3)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 ($16.70 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 (currently $1,000,000) 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 (currently $1,000,000) 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 (currently $500,000) 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 (currently $450,000) 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 (currently $500,000) 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. Sandra Bell— Former Chief Financial Officer Pursuant to the Transition Agreement, Ms. Bell retired as Chief Financial Officer of the Company effective March 31, 2023 and remained employed to assist with special projects until October 15, 2023 and for which she received compensation at her annual base salary rate of $450,000.

  29. 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, 2023. 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 will vest upon Tiptree achieving each of four remaining Tiptree share price target milestones ranging from $20 to $60 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant; the $15 share price target was achieved in 2021. Any unvested PRSUs shall expire on August 4, 2031.

  30. 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 | | | 1,400,000 | $3,679,060 | | | | 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 | 60,217 | 30,109 | $6.26 | 2/26/2029 | | | | | | | | 2/20/2020 | 56,703 | 113,408 | $7.25 | 2/20/2030 | | | | | | Jonathan Ilany | | 1/4/2016 | 137,038 | — | $5.67 | 1/4/2026 | | | 1,400,000 | $3,679,060 | | | | 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 | 90,326 | 45,163 | $6.26 | 2/26/2029 | | | | | | | | 2/20/2020 | 85,055 | 170,111 | $7.25 | 2/20/2030 | | | | | | Randy Maultsby | | | — | — | — | — | — | $— | 466,667 | $1,226,354 | | Sandra Bell | | | — | — | — | — | 26,750(5) | $507,180 | — | $— | | Scott McKinney | | | — | — | — | — | 30,846(6) | $584,840 | 350,000 | $1,521,250 | | Neil C. Rifkind | | | — | — | — | — | 49,414(7) | $936,889 | — | $— |

  31. 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 (a) 30,109 Stock Options granted on February 26, 2019 which will become exercisable on February 26, 2024 and (b) 113,408 Stock Options granted on February 20, 2020 which will become exercisable in equal installments on each of February 26, 2024 and 2025. For Mr. Ilany, the unexercised options consist of (a) 45,163 Stock Options granted on February 26, 2019 which will become exercisable on February 26, 2024 and (b) 170,111 Stock Options granted on February 20, 2020 which will become exercisable in equal installments on each of February 26, 2024 and 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 $18.96 on December 29, 2023 (the last trading day of the year). (4)Consists of PRSUs that vest upon Tiptree satisfying the relevant Tiptree share price target milestones in accordance with the terms of the 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 2023 Annual Report on Form 10-K. (5)Consist of 26,750 RSUs granted to Ms. Bell on February 17, 2022, which will cliff vest on February 20, 2025. Please see “Potential Payments to Named Executive Officers Upon Termination or Change in Control — Sandra Bell” for more information on the treatment of these RSUs following March 31, 2023. (6)Mr. McKinney’s 30,846 unvested RSUs consist of (a) 15,736 RSUs granted to him on February 17, 2022, which will cliff vest 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. (7)Mr. Rifkind’s 49,414 unvested RSUs consist of (a) 26,750 RSUs granted to him on February 17, 2022, which will cliff vest on February 20, 2025 and (b) 22,664 RSUs granted to him on February 22, 2023, which will cliff vest on February 20, 2026, in each case generally subject to Mr. Rifkind’s continued employment with Tiptree.

  32. 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 the vesting of RSUs in 2023. No stock options were exercised by our NEOs during 2023.

  33. Option Exercises and Stock Vested

    | | Stock Awards | | | Name | Number of Shares Acquired on Vesting | Value Realized on Vesting ($)(1) | | Michael G. Barnes | 85,055 | $1,382,994 | | Jonathan Ilany(2) | 127,583 | $2,074,500 | | Randy Maultsby | 10,206 | $165,950 | | Sandra Bell | 5,335 | $86,747 | | Scott McKinney | 1,160 | $18,862 | | Neil C. Rifkind | 5,335 | $86,747 |

  34. Option Exercises and Stock Vested

    ____________________________________ (1) Based on the closing stock price of $16.26 on February 15, 2023, the date the RSUs vested. (2) Mr. Ilany has directed that all the shares to be issued upon vesting of his RSUs and PRSUs be issued to various family trusts. Mr. Ilany has no control over nor pecuniary interest in such family trusts.

  35. 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 Employment Agreement) or due to disability or death, or by such NEO for “good reason” (as defined in the 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 Ms. Bell and 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, 2023, he would have been entitled to receive a total severance of $9,610,163, which represents two times his base salary and the average of his annual cash 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 1,400,000 unvested PRSUs as of December 31, 2023: ◦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 August 4, 2024, 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. 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, 2023, he would have been entitled to receive a total severance of $9,610,163, which represents two times his base salary and the average of his annual cash 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 1,400,000 unvested PRSUs as of December 31, 2023: ◦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 August 4, 2024, 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. 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, 2023, he would have been entitled to receive a total severance of $2,100,000, which represents his base salary and incentive compensation for services performed in 2023. •With respect to Maultsby’s 466,667 unvested PRSUs as of December 31, 2023: ◦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 •Effective March 31, 2023, Mr. McKinney was appointed Chief Financial Officer of the Company. •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, 2023, he would have been entitled to receive a total severance of $1,450,000, which represents his base salary and incentive compensation for services performed in 2023. •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, 2023 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, 2023 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, 2023, with a market value of $584,840 based on the Company’s closing stock price of $18.96 as of December 31, 2023, would become fully vested.

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

    •With respect to McKinney’s 350,000 unvested PRSUs as of December 31, 2023: ◦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, 2023, he would have been entitled to receive a total severance of $1,700,000, which represents his base salary and incentive compensation for services performed in 2023. •If Mr. Rifkind’s employment was terminated by the Company due to his death or disability, then his 49,414 unvested RSUs as of December 31, 2023 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 49,414 unvested RSUs as of December 31, 2023 would remain outstanding and remain eligible for RSU Vesting. •Upon a change of control, Mr. Rifkind’s 49,414 unvested RSUs as of December 31, 2023, with a market value of $936,889 based on the Company’s closing stock price of $18.96 as of December 31, 2023, would become fully vested.

  37. 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 2023, we identified the median employee (such person, the “Median Employee”) by using as our consistently applied compensation measure, 2023 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, 2023, 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 2023 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 2023 annual total compensation of $5,444,695 and $5,525,564, 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 2023 total compensation in the Summary Compensation Table, our Median Employee’s total compensation for 2023 was $77,050. As a result, we estimate that Messrs. Barnes’s and Ilany’s 2023 annual total compensation was approximately 71 times and 72 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.

  38. Pay Versus Performance

    Pay Versus Performance

  39. 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.

  40. 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 | | | | | | | | 2023 | $5,444,695 | $5,525,564 | $13,016,815 | $12,706,949 | $1,851,668 | $2,943,409 | 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 |

  41. 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 2022. (2) 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. The Non-PEO NEOs in 2022 and 2021 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.

  42. 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 | 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 | 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 |

  43. Pay Versus Performance Table

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

  44. 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 | 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 | 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) |

  45. 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 | | 2023 | $1,851,668 | $(157,705) | $1,249,446 | $2,943,409 | | 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 |

  46. Pay Versus Performance Table

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

  47. 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 | | 2023 | $71,621 | $1,053,999 | $94,622 | $24,378 | $— | $4,826 | $1,249,446 | | 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) |

  48. 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.

  49. Key Performance Metrics Table

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