Management Change/Compensation (Form 8-K)

Item 5.02 Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers.

On December 16, 2025, Tiptree Inc. ("Tiptree" or the "Company") appointed its Chief Executive Officer, Jonathan Ilany, non-executive Vice Chairman of the board of directors of the Company (the "Board"), effective January 1, 2026. In connection with this appointment, effective January 1, 2026 Mr. Ilany will transition from his current role as Chief Executive Officer and Michael Barnes, Executive Chairman of the Company, will serve as the Company's Chief Executive Officer. Following such transition, Mr. Ilany will provide consulting and advisory services to the Company to assist with the transition of his duties and responsibilities for one year beginning January 1, 2026 (the "Advisory Period") pursuant to an advisor agreement entered into between the Company and Mr. Ilany dated December 16, 2025 (the "Advisor Agreement"). Mr. Ilany will remain employed as Chief Executive Officer through December 31, 2025.

Pursuant to the terms of the Advisor Agreement, Mr. Ilany will be entitled to, subject to the terms and conditions of the Advisor Agreement, (i) a fee of $500,000 payable in connection with Mr. Ilany's advisory services and for serving as Vice Chairman and a director of the Board during the Advisory Period; (ii) an annual bonus in respect of the fiscal year ending December 31, 2025, payable in cash or shares as determined by the Compensation, Nominating and Governance Committee of the Board (the "CNG"), in an amount determined by the CNG based on the Company's achievement of specific annual corporate performance objectives determined by the CNG; (iii) a cash incentive of 3.5% of Adjusted EBITDA of the Company (as publicly reported by the Company) for the fiscal year ending December 31, 2026; and (iv) at the Company's discretion, continued participation in the Company's group health plans or participation in COBRA benefits, with the payment of the cost of his premiums associated with such coverage borne by the Company through the earlier of December 31, 2026 and Mr. Ilany first becoming eligible for comparable coverage with a subsequent employer or otherwise ceasing to be eligible for COBRA coverage.

The foregoing description of the Advisor Agreement is summary in nature and does not purport to be a complete description of the terms of the Advisor Agreement. Please refer to the Advisor Agreement for full terms. The Advisor Agreement is attached as Exhibit 10.1 under Item 9.01 of this Form 8-K and is incorporated herein by reference.

Mr. Barnes' biographical information set forth in the Company's proxy statement for the Company's 2025 Annual Meeting of Shareholders filed with the U.S. Securities and Exchange Commission on March 17, 2025 (the "2025 Proxy Statement") is incorporated herein by reference.

There are no arrangements or understandings with any other person pursuant to which Mr. Barnes has been appointed as the Company's Chief Executive Officer, and there are no family relationships between Mr. Barnes and any director or executive officer of the Company. Transactions between Mr. Barnes and the Company required to be reported under Item 404(a) of Regulation S-K are set forth in the 2025 Proxy Statement under the section entitled "Transactions with Related Persons-Tiptree Advisors", which disclosure is incorporated herein by reference.

Item 9.01 Financial Statements and Exhibits.