Sean Duffy
About Sean Duffy
Sean Duffy, age 58, is Executive Vice President and Chief Claims Officer at Skyward Specialty Insurance Group (SKWD), serving since January 2019; he also serves as a director of subsidiaries HSIC, IIC, GMIC, and OSIC since March 2019 . He holds a JD from Hamline University and a BA from Carleton College, with ~30 years’ insurance industry experience including senior claims leadership at OneBeacon, Great American Insurance, and Travelers . Company performance in 2024: gross written premiums >$1.7B with 19.4% growth, net income up 38.2% to $118.8M, adjusted combined ratio 91.2%, and ROE 16.3%; A.M. Best rating upgraded to A (Excellent) with stable outlook—metrics that underpin management pay-for-performance constructs .
Past Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| OneBeacon Insurance | SVP, Chief Claims Officer | 2010–2018 | Led specialty claims; built processes and teams to support niche lines |
| Great American Insurance | Senior claims roles | N/D | Senior claims leadership in specialty P&C |
| Travelers | Senior claims roles | N/D | Senior claims leadership in national P&C carrier |
External Roles
The proxy discloses Duffy’s employment history and does not list any external directorships or board roles .
Fixed Compensation
- Duffy is not a named executive officer (NEO); individual base salary, target bonus %, and cash payouts are not disclosed in the proxy .
- Company-wide incentive design (applies to executives, including ELT/NEOs): 2024 Short-Term Incentive Plan (STIP) is driven by two primary metrics—internal combined ratio (CR) and gross written premium (GWP) growth—with OKR-based adjustments. For 2024, the program achieved a 140% payout factor based on internal CR of 91.6% and 19.4% GWP growth .
2024 STIP Framework and Outcome (Program-Level)
| Metric | Target | Actual | Payout Factor | Notes |
|---|---|---|---|---|
| Internal Combined Ratio (CR) | 92.5% | 91.6% | 140% | Performance matrix + OKR achievements used to calibrate awards |
| GWP Growth | 10–15% | 19.4% | 140% | Outcome consistent with profitable growth mandate |
Performance Compensation
- Long-term incentives for executives emphasize performance-based stock units (PSUs) (~67% of LTIP value) split between: (1) three-year internal CR achievement, and (2) three-year relative growth in book value per share (GBVPS) vs peer group; time-based RSUs (~33%) serve retention and alignment .
- PSU payout scales: cap at 150% of target; GBVPS peer percentile mapping: 75th→150%, 50th→100%, 25th→0% .
Executive LTIP Structure (Program-Level)
| Component | Weighting | Metric | Target/Scale | Vesting |
|---|---|---|---|---|
| PSUs (Internal CR) | ~33% of LTIP | 3-year internal CR | 0–150% vest based on CR performance | Eligible at end of 3-year period; certain CIC provisions apply |
| PSUs (Relative GBVPS) | ~33% of LTIP | 3-year GBVPS vs peers | 25th→0%, 50th→100%, 75th→150% | Peer set disclosed; eligible at end of 3-year period |
| RSUs (Time-based) | ~33% of LTIP | Time-based | N/A | Typically single cliff vest (e.g., Jan 1, 2027 for 2024 grants) |
Sean Duffy – Known Award Vesting and Sales
| Date | Event | Shares | Price | Proceeds | Purpose / Notes |
|---|---|---|---|---|---|
| 01/01/2025 | RSA vested (granted 01/01/2022) | 4,305 | N/A | N/A | Form 4 notes full vest of 2022 restricted stock award |
| 01/02/2025 | Sale | 1,475 | $49.02 (WA) | $72,304 | 10b5-1 plan adopted 08/08/2024; sale to cover taxes/fees on vest |
| 03/17/2025 | Sale | 5,625 | $48.90 | $275,062 | Reported subsequent sale; see filings/market summaries |
| 03/06/2025 | Form 144 | N/A | N/A | N/A | Notice of proposed sale under Rule 144 |
After the 01/02/2025 transaction, Duffy reported 8,455 shares beneficially owned; subsequent sales were disclosed via Form 4/144; holdings after later sales should be referenced to each Form 4’s “Amount of Securities Beneficially Owned” line .
Equity Ownership & Alignment
- Beneficial ownership: reported 8,455 shares post 01/02/2025 sale; additional sales disclosed subsequently (see table above and referenced Forms) .
- Ownership guidelines: ELT members must hold Company stock per multiples—CEO 5x base; CFO/Presidents 3x; Other ELT 1x—five-year compliance window; must retain 50% of after-tax shares until in compliance; unearned PSUs/options don’t count .
- Hedging/pledging: prohibited by Insider Trading Policy; margin accounts and hedging transactions are not permitted .
- Clawback: Dodd-Frank compliant recoupment of incentive compensation for restatements in prior three years; equity awards subject to policy .
Employment Terms
- Start date/tenure: EVP & Chief Claims Officer since January 2019; ~6+ years in role .
- Severance (executive officers other than CEO): 12 months of base salary plus 12 months of COBRA premiums upon termination without cause or for good reason; release of claims required .
- Equity treatment: 2023/2024 grants have double-trigger CIC vesting; death/disability and qualifying retirement provisions allow full or prorated vesting with performance measured for completed periods and target assumptions for ongoing periods per award year specifics .
- Confidentiality/non-solicit: Executives must sign the Employee Confidentiality and Non-Solicitation Agreement to receive equity; ongoing compliance required .
Performance & Track Record (Company Context)
| KPI | FY 2023 | FY 2024 | Notes |
|---|---|---|---|
| Gross Written Premiums | ~$1.4–$1.5B (context) | >$1.7B | 19.4% growth to “$1.7+ billion” |
| Net Income | N/D | $118.8M (+38.2% YoY) | Profit growth underscores underwriting/effective claims |
| Adjusted Combined Ratio | N/D | 91.2% | Internal CR used for incentives (adjusted for specific items) |
| ROE | 15.9% | 16.3% | Upper-quartile returns target; pay alignment |
Compensation Structure Analysis (Program-Level Signals)
- Majority of executive pay delivered as variable (STIP + PSUs/RSUs) aligned to CR, GWP, ROE, and GBVPS—reducing guaranteed cash reliance .
- PSU caps, clawbacks, and anti-hedging/pledging policies mitigate excess risk and misalignment .
- 2024 increased target equity values for certain executives to better position vs market medians—suggests retention emphasis within a performance framework .
Related Party Transactions
No related-party transactions disclosed for Duffy in the proxy .
Compensation Peer Group (Benchmarking)
The Compensation Committee references a peer set including AMERISAFE, Employers Holdings, Kinsale, Palomar, RLI, SiriusPoint, Tiptee, Trisura, United Fire Group, Universal Insurance, etc., to calibrate market competitiveness; the company targets compensation within a reasonable range around market median without strict percentile benchmarking .
Say-on-Pay & Shareholder Feedback
2025 presents the first Say-on-Pay and Say-on-Frequency votes; Board recommends “FOR” and annual frequency .
Investment Implications
- Alignment: Duffy’s compensation and ownership are governed by robust policies (clawback, anti-pledging), with program metrics that tie pay to underwriting quality (CR), profitable growth (GWP), and book value accretion (GBVPS)—reducing agency risk .
- Retention/selling pressure: Recent vesting (2022 RSA) and sales under a 10b5-1 plan indicate scheduled liquidity around vest dates; monitor upcoming PSU/RSU measurement and vest cycles for potential insider selling cadence and liquidity events .
- Downside protection: Double-trigger CIC vesting and limited severance (12 months salary + COBRA for executives) temper change-of-control windfalls and limit misaligned payouts, supporting shareholder-friendly economics .