Stephen Sills
About Stephen Sills
Stephen Sills, 76, is Bowhead’s founder and has served as Chief Executive Officer, President, and a director since September 2020. He holds a B.S. in Economics from the University of Tennessee and previously led multiple specialty insurance franchises (Executive Risk, Darwin, CapSpecialty/PRMS), earning industry recognition including the PLUS Founders’ Award . Under his leadership, Bowhead reported strong growth in 2025 with Q3 gross written premiums up 17.5% year over year to $231.5M, net income up 25.5% year over year, and adjusted ROE of 15.1% . The board chair is independent (Matthew Botein), so Sills is not in a combined CEO/Chair role, which supports governance independence .
Past Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| Executive Risk | Founder; Chief Underwriting Officer → CEO | 1987–1999 | Built specialty insurer; sold to Chubb in 1999 |
| Chubb | Executive Vice President | 1999–2001 | Post-acquisition executive role at major carrier |
| Darwin | Chairman, President & CEO | 2003–2008 | Founded and scaled specialty carrier (Darwin) |
| CapSpecialty & PRMS | Chairman & CEO | 2013–2019 | Led specialty P&C and professional liability operations |
| Bowhead Specialty | Founder; CEO, President & Director | 2020–present | Founded Bowhead; led growth and IPO transition |
External Roles
| Organization | Role | Years | Notes |
|---|---|---|---|
| Trusted Resource Underwriters (TRU) | Director | Current | Attorney-in-fact for Florida reciprocal P&C insurer |
| Connecticut Children’s Medical Center | Director | Prior service | Non-profit board experience |
| Professional Liability Underwriting Society (PLUS) | President; Founders’ Award Recipient | Prior service | Industry leadership and recognition |
Fixed Compensation
Multi-Year Compensation (Summary Compensation Table)
| Metric | 2023 | 2024 |
|---|---|---|
| Salary ($) | $643,750 | $669,153 |
| Bonus ($) | $713,790 | $605,168 |
| Stock Awards ($) | — | $3,369,274 |
| All Other Compensation ($) | $35,407 | $35,338 |
| Total ($) | $1,392,947 | $4,678,933 |
Benefits and Perquisites (2024)
| Item | Amount ($) |
|---|---|
| Company 401(k) Contribution | $13,800 |
| Health, Disability, Basic Life Insurance | $17,450 |
| Cell Phone and Internet | $4,088 |
| Total | $35,338 |
Employment Agreement (effective IPO close, May 22, 2024)
- Base salary: $675,000; annual bonus target 100% of salary (max 150%); annual RSUs valued ≥$2,070,000; PSUs granted at $2,200,000 on May 22, 2024 .
- Initial term: 3 years; auto-renewal in 1-year increments unless 90 days’ prior non-renewal notice .
Performance Compensation
Annual Bonus
| Attribute | 2024 Details |
|---|---|
| Target | 100% of base salary |
| Actual Payout | $605,168 (discretionary, service-based) |
| Metric | Discretionary service-based bonus at target amounts |
| Vesting | Cash; paid per plan terms |
RSUs (Restricted Stock Units)
| Attribute | Details |
|---|---|
| Annual Award Value | ≥$2,070,000 during employment |
| Grant Date | May 22, 2024 |
| Outstanding & Unvested (12/31/2024) | 121,764 units; market value $4,325,057 (at $35.52) |
| Vesting Schedule | 20% on each of the 1st, 2nd, 3rd anniversaries; 40% on 4th anniversary (subject to continued employment) |
PSUs (Performance Stock Units)
| Attribute | Details |
|---|---|
| Grant Value | $2,200,000 (May 22, 2024) |
| Outstanding & Unearned (12/31/2024) | 129,411 units; payout value $4,596,679 (at $35.52) |
| Performance Period | May 23, 2024 → May 22, 2027 |
| Performance Metric | Stock price growth goals over 3-year period |
| Vesting | Subject to achievement of stock price growth goals; employment conditions may be waived upon certain severance events |
Equity Ownership & Alignment
| Item | Detail |
|---|---|
| Beneficial Ownership | 951,198 shares (2.9%); includes 214,469 held by Sills 2024 LLC |
| RSUs Unvested (12/31/2024) | 121,764 units; market value $4,325,057 (share price $35.52) |
| PSUs Unearned (12/31/2024) | 129,411 units; value $4,596,679 (share price $35.52) |
| Hedging/Pledging | Prohibited for directors/officers (collars, swaps, margin accounts, pledging) |
| Clawback | SEC/NYSE-compliant recoupment of excess incentive comp for restatement-triggered periods (from Oct 2, 2023; look-back 3 completed fiscal years) |
Vesting cadence and potential selling pressure: RSU tranches are scheduled to vest around May 22 of 2025, 2026, 2027, and 2028, with increasing vesting in year 4 (40%), which can concentrate liquidity events around these dates .
Employment Terms
| Provision | Sills Agreement Details |
|---|---|
| Term & Renewal | 3-year initial term from IPO close (May 22, 2024) with automatic 1-year renewals; 90-day non-renewal notice |
| Severance (no cause / good reason) | 30 months base salary; target annual bonus; earned but unpaid bonus; lump-sum 12 months health premiums; 100% acceleration of time-based equity; waiver of continued employment for performance awards; 30-day notice (company can accelerate with pay in lieu) |
| Change in Control (CIC) | Above amounts payable in lump sum; time-based awards fully vest and settle in cash; buyer may defer payment (rabbi trust) until 1-year post-CIC contingent on continued employment (forfeiture risk unless termination w/o cause, good reason, death/disability) |
| Excise Tax Gross-up | Up to $3,000,000 if CIC occurs within initial employment term and Section 4999 excise tax applies |
| Retirement (non-renewal) | Equity awards accelerate; pro-rata bonus for year of retirement (subject to release and covenant compliance) |
Board Governance
- Board structure: 10 directors, staggered classes; Sills is a Class I nominee with term expiring at the 2028 meeting .
- Leadership: Chair of the Board is Matthew Botein; CEO is Stephen Sills (roles separated), supporting oversight independence .
- Committees: Sills is not listed as a member of the Audit Committee or the Compensation, Nominating and Corporate Governance (CNCG) Committee; these committees include independent directors (Audit chair: David Foy; CNCG chair: Matthew Botein) .
- Independence: Board has affirmed independence for Tom Baker, Angela Brock-Kyle, David Foy, and Ava Schnidman; Sills is not identified as independent (consistent with executive director status) .
- Attendance: Board held two meetings in FY2024; all incumbent directors attended at least 75% of board and committee meetings .
Director Compensation
- Non-employee directors may elect $80,000 cash + $80,000 RSUs or $160,000 RSUs; Audit Committee Chair receives an additional $50,000 cash retainer .
- Employees and nominees of AFMIC/GPC Fund are ineligible for director fees—Sills, as CEO, does not receive separate director compensation .
Performance & Track Record
- Company operating metrics under Sills: Q3 2025 gross written premiums grew 17.5% YoY; net income rose 25.5% YoY; expense ratio improved to 29.5%; adjusted ROE reached 15.1% .
- Non-GAAP reconciliations and divisional growth indicate disciplined underwriting, scaling effects, and improved expense ratios as the platform expands .
Risk Indicators & Red Flags
- CIC Excise Tax Gross-up up to $3,000,000 is shareholder-unfriendly and a governance red flag .
- Hedging and pledging of company stock are prohibited (positive alignment signal) .
- Section 16(a) note: Sills’s initial Form 3 inadvertently omitted a PSU grant and was corrected via amendment filed February 25, 2025 (administrative compliance footnote) .
Compensation Structure Analysis
- Increased equity mix post-IPO: 2024 stock awards for Sills totaled $3,369,274, including RSUs and PSUs, shifting compensation toward long-term equity alignment .
- RSUs vs. PSUs: Introduction of PSUs with stock price growth goals raises alignment with shareholder returns; RSUs maintain retention incentives via 4-year vesting with back-weighted 40% in year 4 .
- Discretionary bonuses at target in 2024 reflect service-based awards; explicit performance weighting beyond PSU stock-price goals not disclosed .
Compensation & Ownership Tables
Outstanding Equity Awards (12/31/2024)
| Award Type | Grant Date | Unvested Units (#) | Market/Payout Value ($) |
|---|---|---|---|
| RSUs | 5/22/2024 | 121,764 | $4,325,057 (at $35.52) |
| PSUs | 5/22/2024 | 129,411 | $4,596,679 (at $35.52) |
Security Ownership
| Holder | Shares | % Outstanding |
|---|---|---|
| Stephen Sills (includes 214,469 via Sills 2024 LLC) | 951,198 | 2.9% |
Investment Implications
- Alignment: Significant personal ownership (2.9%) and PSU structure tied to stock price growth support alignment; hedging/pledging prohibition reduces misalignment risk .
- Retention vs. Liquidity Pressure: RSUs vest 20/20/20/40 over four years, concentrating a large tranche in year 4 (2028), which may create periodic selling pressure around vest dates; PSUs’ three-year window to May 2027 may similarly create event-driven flows .
- Governance and Severance Economics: Separation of CEO and Chair is a positive, but CIC cash settlement of time-based awards and the up-to-$3,000,000 excise tax gross-up elevate potential payout risk in strategic transactions—investors should factor this into M&A scenarios and executive retention economics .
- Execution Track Record: Reported underwriting growth and improving expense ratios suggest disciplined scaling; continued expansion of divisional underwriting (especially Casualty) and investment income support earnings power, but mix shifts can lift loss ratios, requiring vigilance on reserving and acquisition costs .