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Diana Chafey

Chief Legal Officer and Corporate Secretary at Hagerty
Executive

About Diana Chafey

Diana M. Chafey, age 56, is Hagerty’s Chief Legal Officer and Corporate Secretary, a role she has held since 2023. Prior roles include Chief Legal Officer and Corporate Secretary at ATI Physical Therapy (2018–2022), EVP/Chief Legal Counsel and Corporate Secretary at The Warranty Group (TWG Holdings Limited), and partner at DLA Piper LLP (US); she holds a B.A. in Communications (Arizona State University) and a J.D. (Valparaiso University) . Company performance during her tenure shows revenue rising from $787.6M in FY 2022 to $1,200.0M in FY 2024 and net income of $9.6M in FY 2024, with EBITDA improving from negative in 2022 to positive in 2024 (see table below; EBITDA values marked with an asterisk) .

Past Roles

OrganizationRoleYearsStrategic Impact
ATI Physical Therapy (NYSE: ATIP)Chief Legal Officer & Corporate Secretary2018–2022Led legal and corporate secretary functions for a public rehabilitation provider .
TWG Holdings Limited (The Warranty Group)EVP, Chief Legal Counsel & Corporate SecretaryNot disclosedSenior legal leadership for insurance/protection products provider .
DLA Piper LLP (US)PartnerNot disclosedPrivate practice leadership; corporate and insurance-related legal experience .

Fixed Compensation

  • Hagerty discloses compensation in detail only for “named executive officers” (CEO, CFO, plus two most highly compensated execs meeting form criteria). Chafey is not an NEO in FY 2024; her individual salary/bonus/equity details are not disclosed in the proxy .

Performance Compensation

Company-level context (not Chafey-specific): In 2024, the Annual Incentive Plan for named executive officers used Adjusted EBITDA, operating income, and total revenue growth as metrics, weighted 37.5%, 37.5%, and 25%, respectively; plan achievement was 72.6% of target, with board discretion applied to individual payouts for NEOs .

2024 Annual Incentive Plan (NEO context)WeightingTarget DescriptionActual OutcomePayout BasisVesting
Adjusted EBITDA37.5%Company-set annual target72.6% plan factor Base plan factor (discretion may adjust) Cash, annual cycle .
Operating Income37.5%Company-set annual target72.6% plan factor Base plan factor (discretion may adjust) Cash, annual cycle .
Total Revenue Growth25.0%Company-set annual target72.6% plan factor Base plan factor (discretion may adjust) Cash, annual cycle .

Equity plan context (NEO grants): RSUs vest one-third annually over three years; PRSUs earned on a 2024–2026 “aggregate Adjusted Operating Income” target with 35%–200% payout range; CIC provisions allow determination of “Earned PRSUs” and accelerated vesting upon qualifying termination post-CIC; retirement/disability/death provide pro‑rata or full vesting per terms .

Equity Ownership & Alignment

  • Anti-hedging and anti-pledging: Hedging (e.g., zero-cost collars, forwards) and pledging Hagerty securities are prohibited without written approval from the Board and the Chief Legal Officer; this reduces misalignment and involuntary sales risk from collateral foreclosures .
  • Clawback policy: Complies with NYSE Listing Rules and Section 10D; requires recovery of erroneously awarded incentive compensation tied to “Financial Reporting Measures” for the three fiscal years preceding a required restatement .
  • Stock ownership guidelines disclosed for CEO and directors (CEO: 6× base salary; Non-employee directors: 5× annual retainer); officer-specific ownership guidelines beyond CEO are not disclosed .

Employment Terms

  • Appointment: Hagerty named Chafey Chief Legal Officer and Corporate Secretary effective August 2, 2023, succeeding Barbara Matthews; the related 8-K did not file an employment agreement for Chafey .
  • Company equity plan terms (context): RSUs/PRSUs feature time-based and performance-based vesting; certain involuntary terminations post-change-in-control accelerate vesting for earned awards; retirement/disability/death provisions apply to RSUs/PRSUs per plan .
  • Insider trading policy: Prohibits trading on MNPI and tipping; company maintains structured oversight of transactions involving its own securities .

Performance Context

MetricFY 2022FY 2023FY 2024
Revenues (USD)$787,588,000 $1,000,213,000 $1,200,038,000
EBITDA (USD)-$15,355,000*$69,042,000*$105,236,000*
Net Income (USD)$32,078,000 $16,554,000 $9,590,000

*Values retrieved from S&P Global.

  • Hagerty’s revenue grew from $787.6M in FY 2022 to $1,200.0M in FY 2024, while EBITDA shifted from -$15.4M to $105.2M*, indicating improving operating leverage; net income in FY 2024 was $9.6M .
  • The company’s executive incentive framework for NEOs is tied to Adjusted EBITDA, operating income, and revenue growth, signaling management focus on profitability and top-line scale .

Investment Implications

  • Compensation alignment: Anti-hedging/pledging prohibitions and a compliant clawback policy reduce misalignment and restatement risk; however, as an executive who is not an NEO, Chafey’s specific pay mix and targets are not disclosed, limiting direct pay-for-performance assessment .
  • Retention risk: No filed employment agreement or severance terms for Chafey were identified in 8-K appointments; equity vesting protections cited are plan-level and disclosed for NEOs, not specifically for Chafey .
  • Execution backdrop: Company performance trends show strong revenue growth and improved EBITDA*, consistent with incentive metrics used for NEOs (Adjusted EBITDA, operating income, revenue growth), which may indirectly support the legal function’s strategic priorities around transactions, governance, and risk management .
  • Governance signals: The presence of strict anti-hedging/pledging and clawback policies, and board oversight of insider trading, are positive alignment indicators for senior leadership, including the legal function .