DEF 14A of Hagerty, Inc., Apr 30, 2026

DEF 14A of Hagerty, Inc.

Filed Apr 30, 2026 · FY20250001628280-26-028911

Open on EDGAR

  1. Director Compensation

    Director Compensation We have designed our non-employee director compensation program to achieve the following objectives: •align directors’ interests with the long-term interests of our stockholders; •attract and retain outstanding director candidates with diverse experiences, viewpoints and backgrounds; and •recognize the substantial time commitment required to serve as a Hagerty director. Our Nominating and Governance Committee periodically reviews our director compensation program. Independent directors do not receive, directly or indirectly, any consulting, advisory or other compensatory fees from us. Directors who are employees of Hagerty do not receive compensation for their service on our Board. We also reimburse our directors for their reasonable Board travel-related expenses. The following table presents summary information regarding the total compensation paid to the non-employee directors of Hagerty for the year ended December 31, 2025:

  2. Director Compensation

    | Name | Fees earned or paid in cash(1) ($) | Stock awards(2) ($) | All other compensation ($) | Total ($) | | Mike Crowley(3) | 41,591 | 125,558 | – | 167,149 | | Randall Harbert | 97,500 | 125,558 | – | 223,058 | | Laurie Harris | 108,750 | 125,558 | 5,000(4) | 239,308 | | Mike Heaton(5) | 56,216 | 103,835 | – | 160,051 | | Rob Kauffman | 104,000 | 125,558 | – | 229,558 | | Sabrina Kay | 100,000 | 125,558 | – | 225,558 | | Anthony Kuczinski | 92,500 | 125,558 | – | 218,058 | | Mika Salmi | 99,375 | 125,558 | – | 224,933 | | Bill Swanson | 129,625 | 125,558 | – | 255,183 |

  3. Director Compensation

    (1)The amounts shown reflect a blended year in which two compensation levels applied. Through March 31, 2025, our directors were paid a retainer of $85,000 for serving on our Board, $15,000 for serving as the chair of our Audit or Compensation Committee, $8,500 for serving as the chair of our Nominating and Governance Committee or the Finance and Capital Committee, $7,500 for serving on our Audit or Compensation Committee, and $5,000 for serving on our Nominating and Governance Committee or the Finance and Capital Committee. Current director compensation effective April 1, 2025 is set forth in the Compensation Structure table below. (2)Amounts represent the aggregate grant date fair value of restricted stock units granted during the year computed in accordance with ASC Topic 718. Note that the amounts reported in this column reflect the accounting cost for these awards and do not correspond to the actual economic value that our directors may receive from the awards. For all directors other than Mr. Heaton, this column represents the grant of restricted stock units having a target grant value of $125,000 based on the closing stock price on March 31, 2025, which vests 100% on April 1, 2026. Mr. Heaton’s restricted stock units were prorated in connection with his appointment to our Board effective June 3, 2025, and he received restricted stock units having target value of $103,425. To determine the applicable number of shares subject to the award, the target value is divided by the closing Class A stock price on the date immediately preceding the applicable date of grant and rounding up to the nearest whole share. This column also shows the number of shares subject to all outstanding equity awards held by our non-employee directors as of December 31, 2025, which consisted solely of the outstanding RSUs granted to them in 2025. (3)Mr. Crowley retired from our Board on June 3, 2025. In connection with his retirement, 13,828 RSUs held by Mr. Crowley vested in full on June 3, 2025. (4)Includes $5,000 for service on the Hagerty Re board of directors. (5)Mr. Heaton was appointed to our Board effective on June 3, 2025. Hagerty 2026 Proxy Statement 17

  4. Non-Employee Director Compensation Structure

    Non-Employee Director Compensation Structure On February 3, 2025, our Board amended the Non-Employee Director Compensation Structure such that we compensated our non-employee directors, effective April 1, 2025, as follows:

  5. Non-Employee Director Compensation Structure

    | Description | Amount | | Annual Retainer | $85,000 | | Annual Stock Grant | Grant of restricted stock units on April 1 of each year having a target value of $125,000 based on the closing stock price on the prior trading day, rounded up to the nearest whole share, which vests 100% on April 1 of the following year, subject to continued service. | | Additional annual retainers for serving as chairperson of our Board, Lead Director, and chairperson of a Committee | $75,000 for Chair of our Board. However, directors who are also management do not receive additional compensation for serving on our Board. $30,000 for Lead Director. $20,000 for chair of our Audit Committee; $15,000 for chair of our Talent, Culture, and Compensation Committee; and $10,000 for chairs of our Nominating and Governance and Finance and Capital Committees. | | Additional annual retainers for serving on committees | $10,000 for service on our Audit Committee; $7,500 for service on our Talent, Culture, and Compensation Committee; and $5,000 for service on our Nominating and Governance and Finance and Capital Committees. | | Additional retainer for serving on board of directors for Hagerty Re | $5,000 |

  6. Director Nominees

    Director Nominees When filling a vacancy on our Board, the Nominating and Governance Committee identifies the desired skills and experience of a new director nominee and nominates individuals who it believes can strengthen our Board’s capabilities and further expand the collective experience represented by the then-current directors. Our Nominating and Governance Committee may engage third parties to assist in the search and provide recommendations. Also, directors are generally asked to recommend candidates for the position. The candidates would be evaluated based on the processes outlined in the Governance Guidelines and the Nominating and Governance Committee charter, and the same processes would be used for all candidates, including candidates recommended by stockholders (for further information about stockholder director nominations, please see "Commonly Asked Questions and Answers—What is the deadline for submitting a stockholder director nomination or stockholder proposal for the 2027 annual meeting?").

  7. Vote Required for Approval

    | | Laurie Harris | | | Director, member of our Board since 2019 | | | Laurie Harris has served as a member of our Board since Hagerty became a publicly traded company in December 2021. Laurie also served as a member of our Board prior to our initial public offering from December 2019 to 2021. Prior to her retirement in 2018, Laurie was a global engagement audit partner with PricewaterhouseCoopers LLP, one of the largest professional service firms, since 1994 after starting at the firm in October 1992. Since May 2019 Laurie has been a member of the board of directors and audit committee chair of International Workplace Group plc, a public company specializing in co-work and workspace brands, and, from July 2019 until its acquisition in February 2026, served as a member of the board of directors, nominating and governance committee, and audit committee chair of Synchronoss Technologies Inc., a public technology company specializing in cloud platforms and products. Laurie is a Certified Public Accountant, and graduated summa cum laude with a Bachelor of Science degree in Business Administration/Accounting from the University of Southern California. | | | We believe Ms. Harris's experience in the financial services and insurance industries and board leadership experience make her well qualified to serve on our Board. |

  8. Vote Required for Approval

    | | Sabrina Kay | | | Director, member of our Board since 2021 | | | Dr. Sabrina Kay has served as a member of our Board since December 2021. She has served as the CEO of Fremont Private Investments Inc. since 2002, and a Strategic Partner at VSS Capital Since 2021. In 2006, she co-founded Premier Business Bank, which was merged with First Foundation, Inc. in 2018. That same year, she founded Fremont University, where she served as Chancellor and CEO until 2020, integrating a Dale Carnegie franchise into the university's MBA program during her tenure. In 1992, Dr. Kay founded the Art Institute of Hollywood, serving as its CEO and sole owner until its sale to EDMC, a public company, in 2002. Since December 2020, Dr. Kay has been a member of the board of directors and the audit and compensation committees of MannKind Corporation, a public biopharmaceutical company. Since May 2022, she has also served on the board of directors and the compensation and nominating & governance committees at East West Bancorp, Inc., the publicly traded holding company of East West Bank. Dr. Kay holds an MBA from the University of Southern California, an MS in Education, and a doctorate in Work- Based Learning Leadership from the University of Pennsylvania. | | | We believe Dr. Kay's senior management and board leadership experience make her well qualified to serve on our Board. |

  9. Executive Summary

    1Hagerty Re’s Combined Ratio is the ratio of (i) Hagerty Re’s losses, loss adjustment expenses, and underwriting expenses to (ii) its earned premium. Loss and loss adjustment expenses includes the $21 million of reserve reductions in the fourth quarter of 2025 primarily related to favorable developments for the 2024 accident year and improved current accident year experience. Hagerty 2026 Proxy Statement 34 Hagerty aligns executive compensation programs with stockholder interests by tying short- and long-term incentives to specific financial and operational measures and delivering a significant portion of incentives in equity-based compensation. For 2025, Hagerty’s pay-for-performance approach produced compensation outcomes that were closely linked with company performance. The measures tied to our Annual Incentive Plan (“AIP”) in 2025 are an excellent demonstration of this alignment in our short-term incentive program:

  10. Executive Summary

    | 2025 AIP Measure1 | Company Result | Payout (% of Target) | | Adjusted AIP EBITDA (50% weighting) | $238.4M | 150% | | Total Revenue Growth (30% weighting) | 17.9% | 150% | | Policies In Force (PIF) Retention (20% weighting) | 88.7% | 100% | | Total | | 140% |

  11. Executive Summary

    1For a description of how these are defined and measured, see “Compensation Discussion and Analysis—Compensation Elements— Annual Incentive Plan” below. Hagerty’s long-term incentive program ties our NEOs’ compensation to stockholder interests through grants of the following long-term incentive vehicles: •Performance restricted stock units (“PRSUs”): Equity incentive units that convert to Hagerty common stock subject to Hagerty’s actual performance measured against specified performance targets and the recipient’s continued service. For the PRSUs granted in 2025, Hagerty selected cumulative Adjusted Operating Income over the three-year period from 2025 through 2027 for the performance target, which we believe is aligned with long-term stockholder value creation. For a description of how Adjusted Operating Income is defined and measured, see "Compensation Discussion and Analysis—Compensation Elements—Long Term Incentives” below. •Time-based restricted stock units (“RSUs”): Equity incentive units that convert to Hagerty common stock in three equal installments over a three-year period, subject to the recipient’s continued service. Pay policies and practices Our compensation programs reflect industry-wide best practices. We are committed to aligning executive pay with our performance and the interests of our stockholders. Hagerty 2026 Proxy Statement 35

  12. Executive Summary

    | What We Do | What We Don’t Do | | Review pay levels relative to a peer group of comparable companies | Permit repricing of underwater options without stockholder approval | | Grant long-term awards that are at least 50% performance-based | Permit hedging or pledging of Hagerty stock without both Board and Chief Legal Officer written approval | | Cap incentive awards; no payouts below threshold performance levels | Offer excessive perquisites | | Retain an independent consultant engaged by and reporting directly to the Compensation Committee | Count unvested PRSUs towards ownership requirements | | Maintain robust stock ownership guidelines | Use incentive plans that incentivize excessive risk-taking |

  13. Executive Summary

    1.Mr. Hagerty did not receive a time-based RSU award for fiscal 2025; accordingly, his pay mix reflects only base salary, annual incentive, and PRSUs. See "Compensation Elements—Long-term incentives" for further discussion. Hagerty 2026 Proxy Statement 36 NEO Average Pay Mix1

  14. Executive Summary

    1.Due to rounding, the percentages presented in this figure do not total 100%. The target total compensation mix for the CEO is set so that the majority of pay is at risk and performance-based. Given Mr. Hagerty’s significant equity holdings as the Company’s founder, including his indirect ownership through Hagerty Holding Corp. (“HHC”), our Board, on the Compensation Committee’s recommendation, evaluated those holdings and concluded they create meaningful long-term alignment with our stockholders. In light of that analysis, the Board elected to deliver the majority of his compensation through the annual incentive (200% of salary, or $2,400,000, at target). Mr. Hagerty also participates in the long-term incentive plan and, in 2025, received $200,000 in PRSUs. Mr. Hagerty was not granted any time-based RSUs for 2025 due to his meaningful base salary, annual target incentive increase and substantial equity holdings. The Committee’s assessment of Mr. Hagerty’s existing equity alignment through HHC, together with his accountability for short- and long-term performance as CEO and market references for founder CEOs, informed this compensation mix. For the other NEOs, most compensation opportunities are at risk to support Hagerty’s performance-based approach, and long-term incentives make up a greater share of target total compensation to align interests with stockholders. Compensation elements The following chart summarizes the elements of our compensation program:

  15. Executive Summary

    | Compensation Element | Purpose | Annual or Long-Term | Value Delivered: Fixed or Variable | | Base Salary | •Provide a fixed level of cash compensation for performing day- to-day responsibilities | Annual | Fixed | | Annual Incentive Plan | •Reward annual financial and operational performance | Annual | Variable |

  16. Executive Summary

    | Compensation Element | Purpose | Annual or Long-Term | Value Delivered: Fixed or Variable | | Performance Restricted Stock Units | •Align long-term company operating performance to variable compensation opportunity •Align management interests with those of stockholders through changes in share price | Long-Term | Variable | | Time-Based Restricted Stock Units | •Encourage retention and reward long-term company performance •Align management interests with those of stockholders through changes in share price | Long-Term | Variable | | Benefit Plans | •Attract and retain highly-qualified executives •Satisfy executive health, welfare, and retirement needs | Annual | Fixed | | Employment and Termination Arrangements | •Attract and retain highly-qualified executives and protect against uncertainty | Both | Fixed |

  17. Compensation Philosophy and Objectives

    | Reward Long- Term Value Creation | Align executives’ interests with stakeholders. A meaningful portion is delivered in equity to drive growth over a multi-year period. | | Pay for Performance | Compensation plans motivate individuals and teams to take actions that create shareholder value. Exceptional performance is rewarded and poor performance results in a significantly reduced payout. | | Align with Market | Compensation packages are competitive with the external market. The competitive market is primarily defined as similarly-sized insurers but supplemental references may be used for certain roles. | | Evolve to Support Business Strategy | The compensation strategy is flexible to meet evolving business needs and to attract and reward critical talent. | | Reinforce Hagerty’s Mission and Culture | Compensation plans reinforce our purpose to preserve driving and car culture for future generations. |

  18. Compensation-Setting Process

    Compensation-Setting Process In setting annual compensation opportunities, the Compensation Committee considers several factors: •the qualifications of each executive officer and each individual’s time in their role; •the performance of the individual; •internal equity among executives and the impact of each of their roles within the Company; and •practices at peer organizations and other market references. Role of Compensation Committee and management The Compensation Committee is responsible for recommending to the Board pay decisions for the CEO and executive officers, designing and setting targets and ranges for the company’s annual and long-term incentive programs, and recommending for the Board’s approval any grants of long-term compensation awards under the Company’s equity-based long-term incentive program to executive officers. In addition, the Compensation Committee also reviews external compensation policies and programs and evaluates such policies on an annual basis to ensure the Company’s programs serve the Company’s business strategy and stockholder interests, are reasonably informed by market practices, and are aligned with compensation governance best practices. The CEO provides recommendations for executive officer pay decisions (including the NEOs other than the CEO) to the Compensation Committee for ultimate review and recommendation to the Board. Hagerty 2026 Proxy Statement 39 Role of consultant Under its charter, our Compensation Committee has the authority to retain outside counsel or other advisors. The Compensation Committee selected Mercer to serve as its independent executive compensation consultant. Mercer advised our Compensation Committee on executive compensation matters including our compensation philosophy, compensation peer group, and incentive design. Our Compensation Committee assessed Mercer's independence pursuant to the NYSE rules and concluded that its retention of Mercer did not raise any conflicts of interest. In making this assessment, the Compensation Committee considered, among other factors, (i) Mercer’s provision of other services to the Company, (ii) the amount of fees received by Mercer from the Company as a percentage of Mercer’s total revenue, (iii) Mercer’s policies and procedures designed to prevent conflicts of interest, (iv) any business or personal relationships between the Mercer team and members of the Compensation Committee, (v) any Company stock owned by the Mercer team, and (vi) any business or personal relationships between the Mercer team and our executive officers. Peer group benchmarking To assist the Compensation Committee in reviewing and setting executive compensation, monitoring market practices and trends, and evaluating compensation design and pay levels, the Compensation Committee considered data from proxy statements of selected “peer group” companies. The Compensation Committee uses this peer group data as a reference point in evaluating pay levels and program design; it does not apply peer group data using a formal mathematical formula in setting any individual executive’s compensation. For 2025, the peer group included 15 companies in the insurance industry, which were selected because they are similar in size to the Company based on revenue and market capitalization, and because the Company competes with these companies for talent. As of December 31, 2024, when the peer group was used for compensation decisions, the Company’s revenues of $1,242 million and market capitalization of $3,291 million were at the 43rd percentile and 69th percentile, respectively, of the peer group, which had median revenues and market capitalizations of $1,389 million and $1,417 million, respectively. The Company’s 2025 peer group consisted of the following companies: •The Baldwin Insurance Group, Inc. •Donegal Group, Inc. •Erie Indemnity Company •Goosehead Insurance, Inc •Heritage Insurance Holdings, Inc. •Horace Mann Educators Corporation •Kinsale Capital Group, Inc. •Palomar Holdings, Inc. •RLI Corp. •Ryan Specialty Holdings, Inc. •Safety Insurance Group, Inc. •Skyward Specialty Insurance Group, Inc. •Tiptree Inc. •United Fire Group, Inc. •Universal Insurance Holdings Inc.

  19. Compensation Elements

    The Compensation Committee recommended, and the Board approved, structural changes to Mr. Hagerty’s 2025 compensation. Effective January 1, 2025, these changes increased base salary from $850,000 to $1,200,000, increased the target annual incentive opportunity from 100% to 200% of salary, and reduced the annual long-term incentive grant from $1,700,000 to $200,000, provided solely in PRSUs. This change in Mr. Hagerty’s compensation mix to be more heavily weighted toward cash compensation was made in recognition of his significant equity holdings as a member of the founding family of the Company, which primarily derive from his ownership interest in HHC, our controlling stockholder. As reported under “Security Ownership of Certain Beneficial Owners and Management,” HHC beneficially owned 166,552,156 shares of our Class V Common Stock as of April 10, 2026 (approximately 68.95% of that class and 65.98% of total voting power). This existing ownership provides strong alignment with the interests of other stockholders and focuses Mr. Hagerty on continued achievement of our financial objectives. Effective January 1, 2025, Mr. McClymont’s base salary was increased from $575,000 to $650,000 in recognition of his performance and competitive data for Chief Financial Officer compensation. Annual Incentive Plan Our AIP is designed to hold executives accountable, reward performance based on actual business results, and create a pay-for-performance culture. Our Compensation Committee reviews the performance metrics, associated goals, and target incentives under our AIP for each of our named executive officers each year (or otherwise at the time of a new hire or promotion) and recommends for Board approval any adjustments it deems necessary. In February 2025, the Compensation Committee approved the 2025 AIP design. In determining AIP metrics and goals, the Compensation Committee assessed whether the existing performance metrics were adequately linked to our strategy and drove appropriate incentives, whether additional metrics were warranted, and whether any weightings should be adjusted. The Compensation Committee decided to replace the Operating Income metric with Policies in Force (PIF) Retention metric, with a weighting of 20%. This change was designed to reinforce the importance of customer satisfaction and retention to the long‑term growth of the Company. The weightings for Adjusted AIP EBITDA and Total Revenue Growth were set at 50% and 30%, respectively, which were increases and decreases, respectively, to the prior respective weightings for these metrics, and were made to: (i) emphasize durable, high‑quality earnings growth as the Company scales, including operating discipline and loss‑ratio performance that translate revenue into bottom‑line results; and (ii) moderate the weighting on topline growth to avoid over‑incentivizing volume without commensurate profitability, consistent with our philosophy of rewarding growth that is efficient, sustainable, and value‑accretive for stockholders. Calculating Adjusted AIP EBITDA begins with Net Income and adds back interest and other (income) expense, income tax (benefit) expense, and depreciation and amortization. The measure is then adjusted to (i) add back share-based compensation and, when applicable, (ii) exclude restructuring, impairment and related charges, legal settlements and similar items, certain public company or transaction-related costs, and other unusual or non-recurring items approved by the Audit Committee. For AIP purposes, Adjusted AIP EBITDA is measured before AIP expense and holds catastrophe (“CAT”) losses at plan up to $70 million per year. For this metric, CAT losses are weather or catastrophe related losses recognized in our insurance operations under our underwriting and reinsurance practices (for example, severe convective storms, hail, wind, flood, or wildfire events) as determined under our reinsurance program. For AIP purposes, the calculation also excludes net investment income and includes the add‑back of interest paid to State Farm, in each case as Hagerty 2026 Proxy Statement 41 reflected in the Compensation Committee‑approved metric. These AIP‑specific mechanics are intended to focus participants on controllable, plan‑based operating performance and avoid windfalls or penalties from uncontrollable events or weather volatility. Net Income is the most directly comparable GAAP measure. For 2025, the Compensation Committee and the Board determined to award each named executive officer a payout of 100% for the individual performance component under the AIP. While the Compensation Committee has historically differentiated individual performance ratings across NEOs, it concluded this year that all NEOs were high‑performing and met all of their established goals and objectives and that it would not adjust the awarded amount for any named executive officers based on individual performance. In making this determination, the Compensation Committee reviewed each executive’s performance against pre‑set individual objectives aligned with our strategic plan, including: profitable growth and underwriting discipline (reflected in loss‑ratio performance and expense management), execution of marketplace and membership initiatives, advancement of technology and data roadmaps supporting operating leverage, and leadership and talent outcomes. The Compensation Committee also considered that Company performance exceeded plan on the two financial metrics (Adjusted AIP EBITDA and Total Revenue Growth) and met the plan range on Policies in Force Retention, with management delivering results consistent with our pay‑for‑performance philosophy. After reviewing management’s assessment and its own evaluation of each NEO’s achievements and leadership impact, the Compensation Committee determined that a uniform 100% individual performance factor appropriately reflected the year’s results and maintained alignment between pay outcomes and stockholder value creation. Consistent with our AIP design, the Compensation Committee retains discretion to adjust awarded bonus amounts upwards or downwards based on individual performance. While the corporate performance component of the AIP can range from 0% to 150% of target incentive amount, the individual component of the AIP is not subject to a cap. As a result, each of the NEOs is eligible to receive a total AIP payout that exceeds 150% of target. Hagerty 2026 Proxy Statement 42 Below is a summary of each metric and how they align to our strategy:

  20. Compensation Elements

    | Metric | Weight | Rationale for Inclusion | | Adjusted AIP EBITDA (Non- GAAP) | 50% | •Ensures that growth in the business adds to our bottom line •Allows us to measure our progress against our operating plan, which is approved by the Board in December prior to the beginning of the year | | Total Revenue Growth | 30% | •Aligns to our long-term growth strategy •Allows us to measure our progress against our operating plan, which is approved by the Board in December prior to the beginning of the year | | PIF Retention | 20% | •Represents a key measure of customer satisfaction •Indicates the quality of our service model and value proposition to customers |

  21. Compensation Elements

    | Corporate Performance Metric | Threshold Achievement (50% Payout) | Target Achievement (100% Payout) | Maximum Achievement (150% Payout) | Actual Achievement (Metric Value) | Actual Achievement (% of Target) | | Adjusted AIP EBITDA (Non-GAAP)1,2 | $155.5M | $194.4M | $233.2M | $238.4M | 150% | | Total Revenue Growth | 11.1% | 13.9% | 16.7% | 17.9% | 150% | | PIF Retention | 86% | 88-90% | 92% | 88.7% | 100% | | Total | | | | | 140% |

  22. Compensation Elements

    | Officer | Base Salary Paid in 2025($) | 2025 Target Annual Incentive (% Base Salary Paid in 2025) | 2025 Target Annual Incentive($) | Company Performance (% of Target) | Actual Annual Incentive Earned($) | | McKeel Hagerty | 1,185,417 | 200 | 2,370,834 | 140.0 | 3,319,169 | | Patrick McClymont | 646,876 | 100 | 646,876 | 140.0 | 905,626 | | Jeffrey Briglia | 650,000 | 75 | 487,500 | 140.0 | 682,500 | | Russell Page | 650,000 | 75 | 487,500 | 140.0 | 682,500 | | Kenneth Ahn | 600,003 | 75 | 450,002 | 140.0 | 630,003 |

  23. Compensation Elements

    Hagerty 2026 Proxy Statement 43 Hagerty 2026 Proxy Statement 44 Long-term incentives We award long-term incentives to retain talented members of our team and motivate them to achieve long-term financial and strategic objectives. In 2025, our Board approved a 100% PRSU award to our CEO and a 50:50 mix of PRSUs and RSUs for our other NEOs. PRSUs are earned based on achievement against Board-approved performance criteria and are subject to continued service. RSU awards vest subject to continued service. The table below summarizes the key elements of our long-term incentive plan:

  24. Compensation Elements

    | Vehicle | Weighting | Performance Criteria | Vesting Schedule | | Performance Restricted Stock Units | •CEO: 100% •Other NEOs: 50% | •3-year Adjusted Operating Income (100% Weighting) for the 2025-2027 performance period •Continued service | •100% cliff-vesting upon determination, following the three-year performance period, of the performance level actually achieved, subject to continued service through the determination date | | Restricted Stock Units | •CEO: 0% •Other NEOs: 50% | •Continued service | •Pro rata vesting on each of the first three anniversaries of the grant date (33% on each anniversary) |

  25. Compensation Elements

    2025 PRSU Awards The PRSU awards granted to our NEOs on April 1, 2025 vest based on achievement of an aggregate Adjusted Operating Income target (the “2025 PRSUs Performance Target”) measured over January 1, 2025 through December 31, 2027 (the “2025-2027 Performance Period”). The PRSU performance targets are established for incentive compensation purposes and are not intended to constitute, and should not be relied upon as, management guidance, forecasts, or projections regarding our future performance for the applicable performance period. Performance is measured as a percentage of the Hagerty 2026 Proxy Statement 45 2025 PRSUs Performance Target, ranging from a threshold of 70% of the 2025 Grant Performance Target to a maximum of 150% of the 2025 PRSUs Performance Target. Payouts in Class A Common Stock correspond to this range: performance between threshold and target results in 35% to 100% of target shares, and performance between target and maximum results in 100% to 200% of the target shares. In addition, vesting of the PRSU awards is contingent upon the NEO’s continuous employment throughout the 2025-2027 Performance Period and continuing through the date on which our Compensation Committee determines the applicable level of performance attained during the 2025-2027 Performance Period, which is expected to occur in the first calendar quarter following the end of the 2025-2027 Performance Period (the “2025 PRSUs Determination Date”). Any vested PRSUs will be settled into the corresponding number of shares of our Class A Common Stock as soon as reasonably practicable following the 2025 PRSUs Determination Date. In the event of a change in control, our Compensation Committee may determine the number of earned PRSUs based on achievement of the 2025 PRSUs Performance Target immediately prior to the transaction (“Earned PRSUs”). Any Earned PRSUs would be eligible to vest generally subject to the NEO’s continued employment through the date our Compensation Committee determines the applicable level of performance attained. For purposes of determining award achievement for our PRSUs, we calculate “Adjusted Operating Income” from our audited consolidated financial statements by starting with Operating income (loss) as reported in our consolidated statements of operations (or, for periods in which Operating income (loss) is not presented as a separate line item or is not presented on a comparable basis, Operating income (loss) as derived from audited GAAP captions as described below), which is the most directly comparable GAAP measure. Beginning with our Annual Report on Form 10‑K for the year ended December 31, 2025, we present our consolidated financial statements in accordance with Article 7 of Regulation S‑X, which eliminated Operating Income as a line item and repositioned various items within our income statement. Accordingly, to calculate performance on the same basis as the targets we set, for periods where Operating income (loss) is derived for PRSU performance purposes, we derive Operating income (loss) using audited GAAP captions reflected in our consolidated statements of operations, including Income before income taxes and the line items necessary to remove components that were not previously reflected in Operating Income (including Net investment income, Net investment gains, Interest and other income (expense), net, and Loss (gain) related to warrant liabilities, net). In this calculation, “Adjusted Operating Income” is cumulative over the applicable performance period and reflects the sum of the annual Adjusted Operating Income amounts for each year in the performance period. After determining Operating income (loss) as described above, “Adjusted Operating Income” further reflects the following incentive-plan adjustments (each as applicable and as approved for PRSU performance measurement): (i) add back warrant expenses; (ii) add back severance costs; (iii) add back secondary offering costs; (iv) add back legal settlement expense; and (v) for the 2025–2027 PRSU performance period, adjust CAT losses (including variances above or below plan) to the annual CAT assumption used in the plan, subject to the same guardrails applied for the Company’s annual incentive plan CAT-to-plan framework. These adjustments apply solely for incentive compensation purposes. For the avoidance of doubt, any discounts or other risk adjustments applied by our Compensation Committee in establishing the annual or cumulative PRSU target levels for the performance period affect only the target levels and do not change how Adjusted Operating Income is calculated for PRSU performance purposes as described above. 2025 RSU Awards The RSU awards granted to our NEOs on April 1, 2025, as further detailed in the table below, are subject to a time-based vesting requirement with one-third of the RSUs granted vesting into shares of our Class A Common Stock on each of the first, second, and third anniversaries of the grant date, assuming the continued service of the executive officers on each vesting date. Our Board occasionally approves discretionary RSU awards. No discretionary awards were granted to any NEOs in 2025. Hagerty 2026 Proxy Statement 46 On April 1, 2025, our Board approved the grants of RSUs and PRSUs to our NEOs as set forth in the table below.

  26. Compensation Elements

    | Officer | Number of PRSUs Granted | Target Value ($) | Number of RSUs Granted | Target Value ($) | Total Equity Target Value ($) | | McKeel Hagerty | 22,124 | 200,000 | — | — | 200,000 | | Patrick McClymont | 62,915 | 568,750 | 62,915 | 568,750 | 1,137,500 | | Jeffrey Briglia | 53,927 | 487,500 | 53,927 | 487,500 | 975,000 | | Russell Page | 26,964 | 243,750 | 26,964 | 243,750 | 487,500 | | Kenneth Ahn | 24,890 | 225,000 | 24,890 | 225,000 | 450,000 |

  27. Compensation Elements

    The number of shares subject to the PRSUs and RSUs is determined by dividing the target values by the closing trading price on the date preceding the applicable date of grant and rounding up to the nearest whole share. Stock awards are made under the Hagerty, Inc. 2021 Stock Incentive Plan (the "Equity Incentive Plan”). Vested RSUs settle one-for-one in shares of our Class A Common Stock, and PRSUs settle in a range of shares based on achievement against Compensation Committee‑approved goals. All stock awards to our NEOs are subject to certain restrictive covenants, and continued service with us through the vesting date, with exceptions for death, disability, or qualifying retirement. 401(k) Plan We maintain a qualified 401(k) savings plan that allows participants to defer cash compensation up to the maximum amount allowed under IRS guidelines. We make a matching contribution to the plan equal to 100% of the participant’s elective deferral, up to 4% of his or her compensation. Participants are immediately vested in the contributions to the plan. Personal benefits Perquisites for NEOs in 2025 were limited to standard employee benefits, including 401(k) matching and employer‑paid insurance premiums. In addition, executive officers are eligible for Company‑paid executive physicals every 24 months. The value of executive physicals provided in 2025 (if any) was included in “All Other Compensation” for the applicable NEOs and did not exceed the SEC thresholds that would require separate identification and quantification.

  28. Named Executive Officer Compensation Changes in 2026

    Named Executive Officer Compensation Changes in 2026 As part of its annual review in early 2026, the Compensation Committee evaluated the CEO’s target compensation in the context of market practices, pay mix, and alignment with stockholder interests. In doing so, and considering Mr. Hagerty’s substantial existing equity holdings as the Company’s founder, the Compensation Committee determined that increasing the annual incentive opportunity, rather than adding equity, was the best modification to Mr. Hagerty’s compensation to further align his pay with the Company’s performance. After consideration of its assessment of Mr. Hagerty’s strong performance against the Company’s strategic objectives, the Compensation Committee concluded that increasing target opportunity under the AIP was the most appropriate and performance-aligned method to better position Mr. Hagerty’s target total direct compensation relative to market, while avoiding additional equity dilution and maintaining a strong emphasis on variable, at-risk pay. Accordingly, the Compensation Committee recommended, and the Board approved, an increase in Mr. Hagerty’s 2026 target AIP opportunity from 200% to 280% of base salary. This adjustment does not increase fixed compensation and is entirely contingent on achieving rigorous 2026 AIP performance objectives. The Compensation Committee did not increase Mr. Hagerty's base salary and did not grant time‑based equity awards, but approved a grant of PRSUs with a grant‑date fair value of $200,000 for 2025, unchanged from the prior year, reflecting its view that performance‑based cash incentives, combined with meaningful existing equity ownership, provide the strongest alignment for Mr. Hagerty with stockholder outcomes. In addition, as part of the annual review process that took place in early 2026, our Compensation Committee recommended, and our Board approved, changes to target compensation for Mr. Page and Mr. Ahn effective January 1, 2026. Our Board approved an increase in Mr. Page’s target AIP opportunity from 75% to 100% of base salary, and an Hagerty 2026 Proxy Statement 47 increase in target long-term incentive value from $487,500 to $650,000. The Board approved an increase to Mr. Ahn’s base salary from $600,000 to $650,000, and an increase in Mr. Ahn’s target AIP opportunity from 75% to 100% of base salary. These decisions reflect the criticality of these executives for the ongoing growth and success of the Company, ensure the competitiveness of their compensation opportunity versus market references, and maintain a strong pay for performance alignment with a majority of the increases delivered in variable incentive compensation.

  29. Other Compensation Policies and Practices

    Other Compensation Policies and Practices Clawback Policy We have adopted a Policy for Recovery of Erroneously Awarded Incentive Compensation ("Clawback Policy") that complies with the NYSE Listing Rules and Section 10D of the Exchange Act and applies to all of our current or former Section 16 officers. Under the Clawback Policy, we are required to seek to recover "Erroneously Awarded Compensation" as defined in the Clawback Policy, from any affected officer if we are required to prepare an accounting restatement due to our material noncompliance with any financial reporting requirement under securities laws. The Clawback Policy applies to accounting restatements to correct an error in previously issued financial statements that is material to the previously issued financial statement, or that would result in a material misstatement if the error was corrected in the current period or left uncorrected in the current period. The compensation elements subject to clawback or cancellation under the Clawback Policy include any compensation that is granted, earned or vested based in whole or in part on the attainment of a "Financial Reporting Measure" (as defined in the Clawback Policy), in each case, awarded, earned or paid out during the three fiscal years immediately preceding the date on which we were required to prepare the restatement. Our Compensation Committee has full and final authority to make any and all determinations required or permitted under the Clawback Policy. During fiscal 2025, we did not restate any previously issued financial statements and did not recover, and were not required to recover, any incentive‑based compensation under the Clawback Policy. Equity Grant Timing We do not currently grant stock options, stock appreciation rights, or similar option-like instruments. If we anticipate granting such awards in the future, we will establish policies regarding the timing of such grants in relation to the disclosure of material nonpublic information. We have not timed the disclosure of material nonpublic information for the purpose of affecting the value of executive compensation. The 2025 annual equity awards, consisting of performance- based restricted stock units and time-based restricted stock units, were granted on April 1, 2025, consistent with our historical annual grant practice. Compensation-Related Risk Our Compensation Committee periodically reviews our compensation policies and practices for our employees as they relate to risk management and risk-taking incentives. Based on this review, we do not believe that our compensation policies and practices are reasonably likely to have a material adverse effect on the Company. Tax and accounting Section 162(m) of the Code generally disallows a federal income tax deduction for remuneration in excess of $1 million paid in any fiscal year to ‘covered employees,’ including the chief executive officer, chief financial officer and the three other most highly compensated executive officers. In designing our executive compensation program, the Compensation Committee considers our overall compensation goals and what is in the best interests of our stockholders and does not limit executive compensation to that which is or may be deductible under Section 162(m). Hagerty 2026 Proxy Statement 48

  30. Summary Compensation Table

    Summary Compensation Table The following table shows information regarding the compensation of our NEOs for services performed during each of the years indicated below:

  31. Summary Compensation Table

    | Name and Principal Position | Year | Salary ($) | Stock Awards(1) ($) | Non-Equity Incentive Plan Compensation ($)(2) | All Other Compensation(3) ($) | Total ($) | | McKeel Hagerty | 2025 | 1,185,417 | 200,886 | 3,319,169 | 26,660 | 4,732,132 | | CEO | 2024 | 850,001 | 1,700,000 | 617,101 | 39,888 | 3,206,990 | | | 2023 | 850,001 | 700,000 | 765,001 | 64,475 | 2,379,477 | | Patrick McClymont | 2025 | 646,876 | 1,142,536 | 905,626 | 31,919 | 2,726,957 | | CFO | 2024 | 575,001 | 1,756,250 | 521,813 | 38,890 | 2,891,954 | | | 2023 | 575,001 | 1,006,250 | 646,876 | 37,884 | 2,266,011 | | Jeffrey Briglia | 2025 | 650,000 | 979,314 | 682,500 | 27,898 | 2,339,712 | | President of Insurance | | | | | | | | Russell Page | 2025 | 650,000 | 489,666 | 682,500 | 29,368 | 1,851,534 | | CIO | 2024 | 650,000 | 487,500 | 442,406 | 37,721 | 1,617,627 | | Kenneth Ahn | 2025 | 600,003 | 452,002 | 630,003 | 26,497 | 1,708,505 | | President of Marketplace | | | | | | |

  32. Summary Compensation Table

    (1)In accordance with SEC rules, this column reflects the aggregate grant date fair value of the RSU and PRSUs granted to our named executive officers, computed under Financial Accounting Standard Board Accounting Codification Topic 718, as applicable. Assumptions used in the calculation of these amounts are included in Note 21—Share-Based Compensation to our consolidated financial statements in our Annual Report on Form 10-K for the fiscal year ended December 31, 2025. These amounts do not reflect the actual economic value that will be realized by the named executive officer upon the vesting or settlement of the RSUs or PRSUs. If we assume that the highest level of performance conditions will be achieved with respect to the PRSUs (and thus the maximum number of shares will be issued under the PRSUs), the grant date values of the fiscal 2025 stock awards would be as follows: Mr. Hagerty - $401,772, Mr. McClymont - $1,713,805, Mr. Briglia - $1,468,971, Mr. Page - $734,499, and Mr. Ahn - $678,004. (2)Amounts represent the annual cash bonuses paid under our AIP for the applicable year. For a detailed discussion of the AIP, see "Compensation Discussion and Analysis—Compensation Elements—Annual Incentive Plan." (3)Amounts include employer 401(k) matching and executive physical exams. The applicable amounts for each NEO for each category of payments paid in 2025 are set forth in the table below:

  33. Summary Compensation Table

    | Named Executive Officer | 401(k) Matching ($) | Executive Physicals ($) | Group Variable Universal Life ($) | Individual Disability Insurance | Total ($) | | McKeel Hagerty | 14,000 | 0 | 10,320 | 2,340 | 26,660 | | Patrick McClymont | 14,000 | 5,768 | 5,160 | 6,991 | 31,919 | | Jeffrey Briglia | 14,000 | 4,966 | 2,760 | 6,172 | 27,898 | | Russell Page | 14,000 | 5,880 | 2,760 | 6,728 | 29,368 | | Kenneth Ahn | 14,000 | 4,569 | 1,800 | 6,128 | 26,497 |

  34. Summary Compensation Table

    Hagerty 2026 Proxy Statement 51

  35. Grants of Plan-Based Awards in Fiscal 2025

    Grants of Plan-Based Awards in Fiscal 2025 The following table sets forth information regarding grants of plan-based awards made to our NEOs during fiscal 2025.

  36. Grants of Plan-Based Awards in Fiscal 2025

    | Name | Grant Date | Estimated Future Payments Under Non-Equity Incentive Plan Awards(1) | | | Estimated Future Payments Under Equity Incentive Plan Awards (2) | | | All Other Stock Awards: Number of Shares of Stock or Units (#) (3) | Grant Date Fair Value of Stock Awards ($)(4) | | | | Threshold ($) | Target ($) | Maximum ($) | Threshold (#) | Target (#) | Maximum (#) | | | | McKeel Hagerty | | | | | | | | | | | AIP | | 1,185,417 | 2,370,834 | – | | | | | | | PRSU | 4/1/2025 | | | | 7,744 | 22,124 | 44,248 | | 200,886 | | Patrick McClymont | | | | | | | | | | | AIP | | 323,438 | 646,876 | – | | | | | | | PRSU | 4/1/2025 | | | | 22,021 | 62,915 | 125,830 | | 571,268 | | RSU | 4/1/2025 | | | | | | | 62,915 | 571,268 | | Jeffrey Briglia | | | | | | | | | | | AIP | | 243,750 | 487,500 | – | | | | | | | PRSU | 4/1/2025 | | | | 18,875 | 53,927 | 107,854 | | 489,657 | | RSU | 4/1/2025 | | | | | | | 53,927 | 489,657 | | Russell Page | | | | | | | | | | | AIP | | 243,750 | 487,500 | – | | | | | | | PRSU | 4/1/2025 | | | | 9,438 | 26,964 | 53,928 | | 244,833 | | RSU | 4/1/2025 | | | | | | | 26,964 | 244,833 | | Kenneth Ahn | | | | | | | | | | | AIP | | 225,000 | 450,000 | – | | | | | | | PRSU | 4/1/2025 | | | | 8,712 | 24,890 | 49,780 | | 226,001 | | RSU | 4/1/2025 | | | | | | | 24,890 | 226,001 |

  37. Grants of Plan-Based Awards in Fiscal 2025

    (1)The amounts reported in this column represent the threshold and target amounts payable under our AIP. There is no maximum payout under our AIP. Actual bonuses received under the AIP by the named executive officers are reported in the Summary Compensation Table under the column entitled "Non-Equity Incentive Plan Compensation." (2)The amounts reported in these columns reflect the threshold, target and maximum number of PRSUs granted to each of the named executives in fiscal year 2025. The target and maximum amounts are based upon achievement of the Adjusted Operating Income performance measure described in the Compensation Discussion and Analysis section titled “2025 PRSU Awards” over the three calendar-year performance period (FY2025-FY2027). (3)The amounts reported in this column reflect the number of RSUs granted to each of the named executives, other than Mr. Hagerty, in fiscal year 2025. The vesting dates for these RSUs are set forth below in the Outstanding Equity Awards at Fiscal Year-end 2025 Table. (4)The amounts reported in this column represent the aggregate grant date fair value, computed in accordance with FASB ASC Topic 718, of awards of PRSUs and RSUs. See Footnote 1 to the Summary Compensation Table for more information.

  38. Narrative Disclosure to Summary Compensation Table and Grants of Plan-Based Awards Table

    Narrative Disclosure to Summary Compensation Table and Grants of Plan-Based Awards Table Employment Agreements. Each of our NEOs, except for Mr. Page, has entered into a written employment agreement with us that provides for payment of base salary, target annual cash incentive compensation, eligibility for employee benefit programs and potential severance benefits. For further information regarding the base salaries, bonuses and incentive compensation payable to our NEOs and their eligibility for our employee benefit programs, please see our "Compensation Discussion and Analysis" above. For further information regarding the severance benefits provided under their employment agreements, please see “Potential Payments as a Result of Termination or Change in Control (CIC)” below. Hagerty 2026 Proxy Statement 52 Option Repricings and Equity Award Modifications. We did not reprice any stock options or otherwise modify any outstanding equity awards during the year ended December 31, 2025 for our NEOs.

  39. Outstanding Equity Awards at Fiscal Year-End

    Outstanding Equity Awards at Fiscal Year-End The following table sets forth certain information regarding equity awards granted to our named executive officers that were outstanding as of December 31, 2025.

  40. Outstanding Equity Awards at Fiscal Year-End

    | Name | Grant Date | Number of shares, units, or other rights hat have not vested(1) | Market Value of shares, units, or other rights that have not vested(2) | Equity Incentive Plan Awards: Number of unearned shares, units, or other rights that have not vested(1)(4) | Equity Incentive Plan Awards: Market or Payout Value of unearned shares, units, or other rights that have not vested(2) | | McKeel Hagerty | 4/1/2022 | 529,591(5) | $7,117,703 | | | | | 4/1/2022 | | | 3,707,136(6) | $49,823,908 | | | 4/1/2023 | 26,698(3) | $358,821 | | | | | 4/1/2024 | 61,931(3) | $832,353 | | | | | 4/1/2024 | | | 92,896(4) | $1,248,522 | | | 4/1/2025 | | | 22,124(4) | $297,347 | | Patrick McClymont | 4/1/2023 | 38,378(3) | $515,800 | | | | | 4/1/2024 | 36,658(3) | $492,684 | | | | | 4/1/2024 | | | 54,986(4) | $739,012 | | | 12/17/2024 | 68,306(7) | $918,033 | | | | | 4/1/2025 | 62,915(3) | $845,878 | | | | | 4/1/2025 | | | 62,915(4) | $845,878 | | Jeffrey Briglia | 7/1/2024 | 22,436(3) | $301,540 | | | | | 7/1/2024 | 31,250(8) | $420,000 | | | | | 7/1/2024 | | | 46,875(8) | $630,000 | | | 4/1/2025 | 53,927(3) | $724,779 | | | | | 4/1/2025 | | | 53,927(4) | $724,779 | | Russell Page | 4/1/2023 | 18,593(3) | $249,890 | | | | | 4/1/2024 | 17,760(3) | $238,694 | | | | | 4/1/2024 | | | 26,639(4) | $358,028 | | | 4/1/2025 | 26,964(3) | $362,396 | | | | | 4/1/2025 | | | 26,964(4) | $362,396 | | Kenneth Ahn | 4/1/2023 | 17,163(3) | $230,671 | | | | | 4/1/2024 | 16,394(3) | $220,335 | | | | | 4/1/2024 | | | 24,590(4) | $330,490 | | | 4/1/2025 | 24,890(3) | $334,522 | | | | | 4/1/2025 | | | 24,890(4) | $334,522 |

  41. Outstanding Equity Awards at Fiscal Year-End

    (1)The numbers reflected in these columns represent RSUs and PRSUs granted under the Equity Incentive Plan. Each RSU and PRSU vests into shares of our Class A Common Stock under the applicable award agreement, as summarized above under "Stock Awards" and in the following footnotes. (2)The closing price of our Class A Common Stock on December 31, 2025 was $13.44. The amounts reported in these columns are calculated by multiplying (i) the fair market value of common stock on the last day of the fiscal year, which was determined using the closing price on NYSE of a share of common stock by (ii) the number of shares of common stock. Hagerty 2026 Proxy Statement 53 (3)These RSUs vest in one-third increments on each anniversary of the award grant date over a period of three years, The vesting of RSUs may be accelerated or otherwise subject to special treatment in the circumstances described in the section below titled “Potential Payments as a Result of Termination or Change in Control (CIC).” (4)These PRSUs vest at the end of the three-calendar-year performance period that includes the year of grant, subject to certification of the achievement of the relevant performance criteria. The vesting of PRSUs may be accelerated or otherwise subject to special treatment in the circumstances described in the section below titled “Potential Payments as a Result of Termination or Change in Control (CIC).” (5)Reflects an RSU award of 926,784 shares granted to Mr. Hagerty upon the Company’s IPO. 132,397 shares vest in on each anniversary of the grant date until April 1, 2029, subject to Mr. Hagerty’s continued service. (6)Reflects an award granted to Mr. Hagerty upon the Company’s IPO which will vest, if at all, 25% upon Hagerty's Class A common stock trading above $20.00 per share on the NYSE for 60 consecutive days, 25% upon the common stock trading above $25.00 per share on the NYSE for 60 consecutive days, and 50% upon the common stock trading above $30.00 per share on the NYSE for 60 consecutive days prior to April 1, 2029. (7)Reflects an RSU award of 68,306 shares made to Mr. McClymont subject to a time-based vesting requirement with one-third of the RSUs granted vesting into shares of our Class A Common Stock on each of the third, fourth, and fifth anniversaries of the grant date, assuming Mr. McClymont’s continued service on each vesting date. (8)Reflects Mr. Briglia’s PRSU award for fiscal year 2024 which vests on March 1, 2027, subject to the achievement of performance criteria consistent with the 2024 PRSU awards granted to Hagerty’s other NEOs. Hagerty 2026 Proxy Statement 54

  42. Option Exercises and Stock Vested in Fiscal 2025

    Option Exercises and Stock Vested in Fiscal 2025 We do not grant stock options and, accordingly, we had no option exercises during 2025. The following table sets forth the number of shares of common stock acquired during fiscal 2025 by our NEOs upon the vesting of RSUs and the value realized upon such vesting.

  43. Option Exercises and Stock Vested in Fiscal 2025

    | | STOCK AWARDS | | | Name | Number of Shares Acquired Upon Vesting (#) | Value Realized on Vesting ($)(1) | | McKeel Hagerty | 242,578 | 2,202,608 | | Patrick McClymont | 75,244 | 736,422 | | Jeffrey Briglia | 26,842 | 255,728 | | Russell Page | 34,888 | 388,067 | | Kenneth Ahn | 36,943 | 335,442 |

  44. Option Exercises and Stock Vested in Fiscal 2025

    (1)Calculated by multiplying (i) the fair market value of common stock on the vest date, which was determined using the closing price on NYSE of a share of common stock on the date of vest, or if such day is a holiday, on the immediately preceding trading day, by (ii) the number of shares of common stock acquired upon vesting.

  45. Pension Benefits and Nonqualified Deferred Compensation

    Pension Benefits and Nonqualified Deferred Compensation We do not maintain any defined benefit pension plans, supplemental executive retirement plans, or nonqualified deferred compensation plans for our named executive officers. Accordingly, no pension benefits or nonqualified deferred compensation tables are presented.

  46. Potential Payments as a Result of Termination or Change in Control

    Potential Payments as a Result of Termination or Change in Control The following tables show the estimated payments and benefits payable to each NEO under various scenarios related to a termination of employment, including in connection with a change in control, and reflect only amounts that are increased, accelerated or otherwise payable as a result of the applicable scenario. The tables assume that each termination of employment occurred on December 31, 2025, and the estimated amounts are based on compensation, benefit and equity levels in effect on that date and the terms of the employment agreements (or other arrangements) and applicable equity award agreements. The estimated payments and benefits set forth below are in addition to any retirement, welfare and Hagerty 2026 Proxy Statement 57 other benefits that are available to our employees generally. The actual amounts that would be paid to any NEO can only be determined at the time of an actual termination of employment and may vary from those set forth below. In establishing and periodically reviewing these arrangements, the Compensation Committee and Board consider them as part of the NEO’s overall compensation package and evaluate, among other factors, the executive’s role and scope of responsibilities, experience and performance, internal pay equity, and market practices and compensation levels at peer companies (including with input from the Compensation Committee’s independent compensation consultant). Consistent with these considerations, the cash severance and benefit continuation amounts shown in the tables are calculated by applying the applicable contractual severance provisions (including any salary continuation periods or multiples and incentive compensation treatment) to compensation levels in effect on December 31, 2025, and the equity-related amounts reflect the treatment of outstanding awards under the applicable award agreements (and, where applicable, assumptions regarding performance through December 31, 2025). Qualifying Termination other than Death, Disability or Retirement Not in Connection with Change in Control

  47. Potential Payments as a Result of Termination or Change in Control

    | | Cash Payments | | | Equity Acceleration or Continuation | | | | Named Executive Officer | Salary ($) | Annual Incentive Plan ($)(1) | COBRA ($) | Shares(2) | Market Value of Accelerated Equity ($)(2) | Total ($) | | McKeel Hagerty | 2,400,000 | 8,119,169 | 27,936 | 533,549 | 7,170,899 | 17,718,004 | | Patrick McClymont | 975,000 | - | 1,746 | - | - | 976,746 | | Jeffrey Briglia | 650,000 | - | 4,333 | - | - | 654,333 | | Russell Page | 86,437 | - | 1,746 | - | - | 88,183 | | Kenneth Ahn | 600,000 | - | 1,746 | - | - | 601,746 |

  48. Potential Payments as a Result of Termination or Change in Control

    (1)For Mr. Hagerty, value reflects the sum of two times his annualized AIP target value plus the actual AIP value earned for 2025. (2)For Mr. Hagerty, value reflects the number of RSUs and PRSUs estimated to vest during the two year period following his termination, assuming an estimated level of actual performance for his outstanding PRSUs based on performance attained through December 31, 2025. Death Termination Not in Connection with Change in Control

  49. Potential Payments as a Result of Termination or Change in Control

    | | Cash Payments | | | Equity Acceleration or Continuation | | | | Named Executive Officer | Salary ($) | Annual Incentive Plan ($)(1) | COBRA ($) | Shares(2) | Market Value of Accelerated Equity ($)(3) | Total ($) | | McKeel Hagerty | - | 3,319,169 | - | 748,362 | 10,057,985 | 13,377,154 | | Patrick McClymont | - | - | - | 305,941 | 4,111,847 | 4,111,847 | | Jeffrey Briglia | - | - | - | 163,382 | 2,195,854 | 2,195,854 | | Russell Page | - | - | - | 110,012 | 1,478,561 | 1,478,561 | | Kenneth Ahn | - | - | - | 101,551 | 1,364,845 | 1,364,845 |

  50. Potential Payments as a Result of Termination or Change in Control

    (1)For Mr. Hagerty, value reflects his actual AIP value earned for 2025. (2)Upon an NEO’s death, all unvested RSUs fully accelerate and PRSUs accelerate based on actual performance prorated for the performance period elapsed. The amounts listed in the table above reflect the applicable pro-rata number of PRSUs that would accelerate vesting due to the NEO’s death, assuming an estimated level of actual performance for the PRSUs based on performance attained through December 31, 2025. (3)Calculated by multiplying (i) the fair market value of common stock on the vest date, which was determined using the closing price on NYSE of a share of common stock on the date of vest, or if such day is a holiday, on the immediately preceding trading day, by (ii) the number of shares of common stock acquired upon vest. Hagerty 2026 Proxy Statement 58 Disability Termination Not in Connection with Change in Control

  51. Potential Payments as a Result of Termination or Change in Control

    | | Cash Payments | | | Equity Acceleration or Continuation | | | | Named Executive Officer | Salary ($) | Annual Incentive Plan ($)(1) | COBRA ($) | Shares(2) | Market Value of Accelerated Equity ($)(3) | Total ($) | | McKeel Hagerty | 2,400,000 | 8,119,169 | 27,936 | 748,362 | 10,057,985 | 20,605,090 | | Patrick McClymont | 975,000 | - | - | 305,941 | 4,111,847 | 5,086,847 | | Jeffrey Briglia | - | - | - | 163,382 | 2,195,854 | 2,195,854 | | Russell Page | - | - | - | 110,012 | 1,478,561 | 1,478,561 | | Kenneth Ahn | 600,000 | - | - | 101,551 | 1,364,845 | 1,964,845 |

  52. Potential Payments as a Result of Termination or Change in Control

    (1)For Mr. Hagerty, value reflects the sum of two times his annualized AIP target value plus the actual AIP value earned for 2025. (2)Upon an NEO’s termination in connection with Disability, all unvested RSUs fully accelerate and PRSUs accelerate based on actual performance prorated for the portion of the performance period elapsed prior to termination. The amounts listed in the table above reflect the applicable pro-rata number of PRSUs that would accelerate vesting due to the NEO’s Disability, assuming an estimated level of actual performance for the PRSUs based on performance attained through December 31, 2025. (3)Calculated by multiplying (i) the fair market value of common stock on the vest date, which was determined using the closing price on NYSE of a share of common stock on the date of vest, or if such day is a holiday, on the immediately preceding trading day, by (ii) the number of shares of common stock acquired upon vest. Retirement Termination in Not in Connection with Change in Control

  53. Potential Payments as a Result of Termination or Change in Control

    | | Cash Payments | | | Equity Acceleration or Continuation | | | | Named Executive Officer | Salary ($) | Annual Incentive Plan ($)(1) | COBRA ($) | Shares(2) | Market Value of Accelerated Equity ($)(3) | Total ($) | | McKeel Hagerty(4) | - | 3,319,169 | - | 272,688 | 3,664,927 | 6,984,096 |

  54. Potential Payments as a Result of Termination or Change in Control

    (1)For Mr. Hagerty, value reflects his actual AIP value earned for 2025. (2)Each NEO who terminates employment due to retirement is eligible to vest in a pro-rata portion of the RSUs that would have otherwise vested on the next scheduled annual vesting date, and with such pro-rata portion calculated by reference to the total number of days that the executive was employed during such interim vesting period divided by the total number of days in such vesting period. The share amounts listed in the table above reflect the applicable pro-rata vesting of the outstanding RSUs and an applicable pro-rata number of PRSUs that would accelerate vesting due to a qualified retirement assuming an estimated level of performance for the PRSUs based on performance attained through December 31, 2025. (3)Calculated by multiplying (i) the fair market value of common stock on the vest date, which was determined using the closing price on NYSE of a share of common stock on the date of vest, or if such day is a holiday, on the immediately preceding trading day, by (ii) the number of shares of common stock acquired upon vest. (4)As of December 31, 2025, Mr. Hagerty was the only NEO who was eligible to terminate employment due to a qualified retirement. Hagerty 2026 Proxy Statement 59 Involuntary Termination in Connection with Change in Control

  55. Potential Payments as a Result of Termination or Change in Control

    | | Cash Payments | | | Equity Acceleration or Continuation | | | | Named Executive Officer | Salary ($) | Annual Incentive Plan ($)(1) | COBRA ($) | Shares(2) | Market Value of Accelerated Equity ($)(3) | Total ($) | | McKeel Hagerty | 2,400,000 | 8,119,169 | 27,936 | 828,552 | 11,135,336 | 21,682,441 | | Patrick McClymont | 975,000 | - | 1,746 | 398,691 | 5,358,407 | 6,335,153 | | Jeffrey Briglia | 650,000 | - | 4,333 | 228,044 | 3,064,911 | 3,719,244 | | Russell Page | 86,437 | - | 1,746 | 151,749 | 2,039,507 | 2,127,690 | | Kenneth Ahn | 600,000 | - | 1,746 | 140,077 | 1,882,635 | 2,484,380 |

  56. Potential Payments as a Result of Termination or Change in Control

    (1)For Mr. Hagerty, value reflects the sum of two times his annualized AIP target value plus the actual AIP value earned for 2025. (2)The share amounts listed in the table above reflect the number of RSUs that would accelerate vesting and the estimated applicable number of PRSUs that would accelerate vesting based on performance attained through December 31, 2025. (3)Calculated by multiplying (i) the fair market value of common stock on the vest date, which was determined using the closing price on NYSE of a share of common stock on the date of vest, or if such day is a holiday, on the immediately preceding trading day, by (ii) the number of shares of common stock acquired upon vest.

  57. Pay Versus Performance Table

    Pay Versus Performance Table The following table sets forth information concerning: (1) the compensation of our Principal Executive Officer (“PEO”) (Mr. Hagerty – Chairman and Chief Executive Officer) and the average compensation for our other Named Executive Officers (“Non-PEO NEOs”), both as reported in the Summary Compensation Table and with certain adjustments to reflect the “compensation actually paid” to such individuals, as defined under SEC rules, for each of the fiscal years ended December 31, 2023, 2024, and 2025 and (2) our cumulative total shareholder return (“TSR”), the cumulative TSR of our selected peer group (“S&P 500 P&C Insurance Index”), Net Income and Adjusted AIP EBITDA (our Company-Selected Measure) over such years, in each case determined in accordance with SEC rules:

  58. Pay Versus Performance Table

    | (a) | (b) | (c) | (d) | (e) | (f) | (g) | (h) | (i) | | | | | | | Value of Initial Fixed $100 Investment Based on: | | | | | Year | Summary Compensation Table Total for PEO ($) (1) | Compensation Actually Paid to PEO ($) (1)(2) | Average Summary Compensation Table Total for Non-PEO NEOs ($) (1) | Average Compensation Actually Paid to Non-PEO NEOs ($) (1)(2) | Total Shareholder Return ($) (3) | S&P 500 P&C Insurance Index Total Shareholder Return ($) (3) | Net Income (millions) | Adjusted AIP EBITDA (millions) (4) | | 2025 | 4,732,132 | 16,027,578 | 2,156,036 | 3,278,158 | 159.81 | 165.26 | $149.23 | $238.4 | | 2024 | 3,206,990 | 6,951,558 | 2,245,582 | 2,505,862 | 114.74 | 150.13 | $78.30 | $164.8 | | 2023 | 2,379,477 | 1,450,376 | 2,425,368 | 2,302,804 | 92.75 | 110.81 | $28.18 | $103.4 |

  59. Pay Versus Performance Table

    (1)The following individuals are our other Named Executive Officers for each fiscal year:

  60. Pay Versus Performance Table

    | Year | PEO(s) | Non-PEO NEOs | | 2025 | McKeel Hagerty | Patrick McClymont, Jeffrey Briglia, Russell Page, Kenneth Ahn | | 2024 | McKeel Hagerty | Patrick McClymont, Russell Page, Paul Rehrig | | 2023 | McKeel Hagerty | Patrick McClymont, Paul Rehrig |

  61. Pay Versus Performance Table

    (2)Compensation actually paid to our NEOs represents the “Total” compensation reported in the Summary Compensation Table for the applicable fiscal year, adjusted as follows: Hagerty 2026 Proxy Statement 60

  62. Pay Versus Performance Table

    | Adjustments | 2023 | | 2024 | | 2025 | | | | PEO | Average Non-PEO NEOs | PEO | Average Non-PEO NEOs | PEO | Average Non-PEO NEOs | | Summary Compensation Total for Applicable FY | $2,379,477 | $2,425,368 | $3,206,990 | $2,245,582 | $4,732,132 | $2,156,036 | | Deduction for Amounts Reported under the “Stock Awards” Column in the Summary Compensation Table for Applicable FY | ($700,000) | ($909,375) | ($1,700,000) | ($1,018,750) | ($200,886) | ($765,880) | | Increase based on ASC 718 Fair Value of Awards Granted during Applicable FY that Remain Unvested as of Applicable FY End, determined as of Applicable FY End | $624,718 | $811,571 | $2,689,339 | $1,293,026 | $405,911 | $1,339,959 | | Increase based on ASC 718 Fair Value of Awards Granted during Applicable FY that Vested during Applicable FY, determined as of Vesting Date | — | — | — | — | — | — | | Increase/deduction for Awards Granted during Prior FY that were Outstanding and Unvested as of Applicable FY End, determined based on change in ASC 718 Fair Value from Prior FY End to Applicable FY End | ($932,171) | ($26,677) | $2,263,992 | $139,967 | $11,228,691 | $551,203 | | Increase/deduction for Awards Granted during Prior FY that Vested During Applicable FY, determined based on change in ASC 718 Fair Value from Prior FY End to Vesting Date | $78,353 | $1,917 | $491,237 | $72,438 | ($138,269) | ($3,160) | | Deduction of ASC 718 Fair Value of Awards Granted during Prior FY that were Forfeited during Applicable FY, determined as of Prior FY End | — | — | — | ($226,400) | — | — | | Increase based on Dividends or Other Earnings Paid during Applicable FY upon Vesting Date | — | — | — | — | — | — | | TOTAL ADJUSTMENTS | $1,450,376 | $2,302,804 | $6,951,558 | $2,505,862 | $16,027,578 | $3,278,158 |

  63. Pay Versus Performance Table

    (3)TSR is cumulative for the measurement periods beginning on December 31, 2022 and ending on each of December 31, 2023, December 31, 2024, and December 31, 2025, respectively, calculated in accordance with Item 201(e) of Regulation S-K. The selected industry index for this calculation is the S&P 500 Property & Casualty Insurance Index. (4)Adjusted AIP EBITDA is our Company‑Selected Measure. Our Compensation Committee reviews Adjusted AIP EBITDA on a quarterly basis to inform annual non‑equity incentive plan compensation determinations for our NEOs. We define Adjusted AIP EBITDA as consolidated Net Income, excluding net interest and other income (expense), income tax (benefit) expense, and depreciation and amortization. The measure is then adjusted to (i) add back share-based compensation and, when applicable, (ii) exclude restructuring, impairment and related charges, legal settlements and similar items, certain public company or transaction- related costs, and other unusual or non-recurring items approved by the Audit Committee. For AIP purposes, Adjusted AIP EBITDA is measured before AIP expense and holds CAT losses at plan up to $70 million per year. For this metric, CAT losses are weather or catastrophe related losses recognized in our insurance operations under our underwriting and reinsurance practices (for example, severe convective storms, hail, wind, flood, or wildfire events) as determined under our reinsurance program. For AIP purposes, the calculation also excludes net investment income and includes the add back of interest paid to State Farm, in each case as reflected in the Compensation Committee approved metric. These AIP specific mechanics are intended to focus participants on controllable, plan based operating performance and avoid windfalls or penalties from uncontrollable events or weather volatility. Net Income is the most directly comparable GAAP measure. Hagerty 2026 Proxy Statement 61

  64. Narrative Disclosure to Pay Versus Performance Table

    Narrative Disclosure to Pay Versus Performance Table Relationship between Financial Performance Measures The line graphs below compare (i) the compensation actually paid to our PEO and the average of the compensation actually paid to our remaining NEOs, with (ii) our cumulative TSR, (iii) S&P 500 P&C Insurance Index TSR, (iv) our Net Income , and (v) our Adjusted AIP EBITDA, in each case, for the fiscal years ended December 31, 2023, 2024, and 2025. TSR amounts reported in the graph assume an initial fixed investment of $100, and that all dividends, if any, were reinvested. Hagerty 2026 Proxy Statement 62 Hagerty 2026 Proxy Statement 63 Pay Versus Performance Tabular List The following performance measures represent the most important financial performance measures used by us to link compensation actually paid to our NEOs to performance for the fiscal year ended December 31, 2025: •Adjusted AIP EBITDA •Total Revenue Growth •Policies in Force Retention •Adjusted Operating Income Hagerty 2026 Proxy Statement 64