Tiptree Inc

This management proposal seeks shareholder approval to adopt Amendment No. 2 to the Company’s 2017 Omnibus Incentive Plan to (i) extend the plan’s term to June 6, 2037 and (ii) increase the share reserve by 4,000,000 shares (raising the total authorized under the plan to 14,100,000 shares). Management and the CNG Committee argue the extension and share increase are necessary because the existing plan is scheduled to expire on June 6, 2027 and only 413,369 shares remain available for future grants as of February 28, 2026, which the Board believes is insufficient to continue historical grant practices and to support recruiting and retention, particularly in connection with potential acquisitions. The filing discloses historical grant activity (notably large PRSU grants in 2021 and 2024 tied to high-priced performance hurdles) and presents the Board’s view that most outstanding PRSUs vest only upon extraordinary stock-price performance, which limits near-term dilution risk. The Board also quantifies current overhang and how the additional 4,000,000 shares would increase overhang from approximately 12.6% to about 20.9% on a pro-forma basis, a figure that may draw scrutiny from governance advisors and some investors. The proposal explains that using equity awards supports M&A by enabling the Company to retain management teams at acquired businesses and preserves cash for transaction and integration needs. Vote mechanics require a majority of votes cast for approval; abstentions and broker non-votes are not counted as votes cast. From a governance and dilution perspective, investors should weigh the Company’s argument that a substantial portion of outstanding PRSUs are equity that will only pay out upon significant share-price appreciation against the near-term increase in potential dilution and the Company’s historical burn rate. The CNG Committee indicates it will continue to manage issuance prudently through vesting conditions, performance metrics, and attention to burn-rate and dilution. In sum, the proposal asks shareholders to grant the Board greater long-term flexibility to use equity compensation as a retention and transaction tool while accepting a notable increase in authorized dilution, buffered by performance-contingent PRSUs and the Board’s stated governance controls.

This non-binding management proposal asks shareholders to approve the Company’s executive compensation disclosure and program for the named executive officers as presented in the CD&A and related tables. Management frames pay as strongly pay-for-performance: a large portion of NEO compensation is variable and equity-based (including PRSUs with demanding stock-price hurdles), and annual cash incentives are tied to Adjusted EBITDA. The Board and CNG Committee emphasize use of an independent compensation consultant, clawback policies, minimum vesting, and caps on director compensation as safeguards, and note that the 2023 Say-on-Pay received approximately 71% support and that management has engaged with large stockholders. Because the vote is advisory, it does not change pay arrangements directly but signals shareholder sentiment that the Board and CNG Committee are expected to consider when making future decisions; significant negative outcomes could prompt revisions to plan design or heightened engagement. From an investor perspective, important considerations include the magnitude and structure of recent PRSU grants (with large performance hurdles that limit immediate dilution), the total compensation paid to the CEO/PEO relative to median employee pay, and whether the CNG Committee’s disclosures demonstrate sufficient alignment and risk mitigation. The filing shows that the Company’s pay mix is heavily weighted to variable compensation (76% variable in 2025), which supports management’s alignment argument but may also concentrate realized pay on successful stock-price appreciation. In summary, this proposal is a standard Say-on-Pay vote where shareholders can endorse or express concerns about the Board’s compensation choices; while non-binding, a negative vote would likely trigger further Board engagement with investors and potential program adjustments.

This advisory proposal asks shareholders to select the frequency (1, 2, or 3 years) for future advisory Say-on-Pay votes; the Board recommends every three years. Management argues three years strikes a balance by allowing investors to assess the effectiveness of compensation changes over a meaningful period aligned with long-term strategy while avoiding excessive focus on short-term results. Practically, the option receiving the plurality of votes will be treated as the stockholder recommendation; the result is advisory and not binding on the Board or CNG Committee, which retains discretion to set frequency. From a governance standpoint, many companies and proxy advisory firms prefer triennial votes when compensation programs emphasize long-term equity awards tied to multi-year performance metrics; however, some investors prefer annual votes for more frequent accountability. Stockholders should consider the Company’s use of long-term PRSUs with multi-year performance periods, the Board’s engagement history with large holders, and whether a three-year cadence provides an appropriate timeline to observe the outcomes of compensation changes. Given the Company’s stated focus on long-term value creation and the multi-year nature of its PRSUs, the Board’s recommendation for a three-year frequency is consistent with its compensation design, but shareholders who prioritize more frequent direct input may favor annual or biennial votes. The advisory nature of the vote means that even if stockholders select a different frequency, the Board may consider but is not legally required to adopt that frequency.