Andrew Robinson
About Andrew Robinson
Andrew Robinson, age 59, is Chairman of the Board and Chief Executive Officer of Skyward Specialty Insurance Group (SKWD); he has served as CEO since May 2020, joined the Board in July 2020, and was appointed Chairman in December 2023. He holds a B.S. from Clarkson University and brings a 30-year track record across insurance, claims, and technology leadership roles . Operationally, SKWD delivered 2024 gross written premium growth of 19.4%, net income of $118.8M (+38.2% YoY), an adjusted internal combined ratio of 91.2%, ROE of 16.3%, and an A.M. Best upgrade to “A, Excellent”; 2024 PEO “compensation actually paid” and TSR metrics reflect strong performance alignment (2024 CAP $17.05M; SKWD TSR $264.61 vs peer TSR $128.30) . Board structure features a combined CEO/Chair role offset by a Lead Independent Director and regular executive sessions to preserve independent oversight .
Past Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| Oak HC/FT (portfolio) | Executive in Residence/Senior Advisor; Co-CEO then Executive Chair (Groundspeed Analytics); Chair (Clara Analytics) | Pre-2020 | Brought insurtech operating and governance experience into SKWD leadership . |
| Crawford & Company | Global COO & EVP | Jan–Jul 2017 | Oversaw four businesses with ~$1.1B revenue and 8,000+ employees; operations and execution depth . |
| The Hanover Insurance Group | President, Specialty Insurance; EVP, Corporate Development; Chief Risk Officer | ~10+ years | Led U.S. specialty P&L; M&A, integration, and ERM leadership . |
| Diamond (now PwC) Consulting | Managing Partner, Global Insurance | Prior to Hanover | Strategic transformation expertise in insurance . |
External Roles
| Organization | Role | Years | Notes |
|---|---|---|---|
| McLarens, Inc. | Director | Current | Global insurance services board role . |
| Chaucer Plc (Lloyd’s agency) | Director | Prior | Prior public insurance market governance experience . |
| PLNAR (insurtech) | Director | As disclosed in 2024 proxy | Additional insurtech board activity disclosed in 2024 . |
Fixed Compensation
| Metric | 2022 | 2023 | 2024 |
|---|---|---|---|
| Base Salary ($) | 787,500 | 800,000 | 900,000 |
| Target Bonus (% of Salary) | 100% (plan) | 100% | 125% (Target $1,125,000) |
| Actual Cash Bonus ($) | 1,040,000 (2022 performance) | 1,600,000 (2023 performance) | 1,575,000 (2024 performance) |
Notes: 2024 target bonus increased to 125% to enhance pay-at-risk; 2024 STIP paid at 140% on strong profitable growth .
Performance Compensation
Short-Term Incentive Plan (STIP) – Design and 2024 Outcome
| Metric | Target/Scale | Actual (2024) | Payout |
|---|---|---|---|
| Internal Combined Ratio (CR) | 92.5% target (matrix-based) | 91.6% internal CR | 140% of target (with OKR overlay) |
| GWP Growth | 10–15% target band | 19.4% growth | Included in 140% outcome |
| OKRs (talent, tech/data, execution, disruption, fortify position) | Discretionary overlay | “Exceptional achievement” | Supported 140% decision |
Long-Term Incentives (LTI) – Structure and Grants
| Year | Vehicle | Metric(s) | Target Grant Value ($) | Key Dates |
|---|---|---|---|---|
| 2024 | ~67% PSUs / ~33% RSUs | PSUs: 50% 3-yr internal CR; 50% 3-yr relative GAAP BVPS vs peer set; cap 150%. RSUs time-based . | 1,500,000 (increase from $900,000 in 2023) | Grant: 2/27/24; PSUs perf period 2024–2026; RSUs vest 1/1/2027 . |
| 2023 | PSUs/RSUs/Options (IPO awards also granted) | Two PSUs (CR, relative BVPS predecessor); RSUs; NQSOs . | 900,000 (PSUs/RSUs); additional IPO RSUs/Options separately disclosed . | RSUs vest 1/1/2026–1/1/2027; Options vest 50% 1/12/2026 & 50% 1/12/2027 . |
2024 Grant Detail (Andrew Robinson):
- RSUs: 14,959 units granted 2/27/24; scheduled to vest 1/1/2027 .
- PSUs: aggregate target 29,918 units across two awards; performance period 2024–2026; cap 150% .
- 2022–2024 legacy PSUs (relative GTBVPS) at target 22,796 for PEO; vesting eligibility completed 12/31/24; settlement anticipated May 2025 when peer BVPS data finalizes .
Equity Ownership & Alignment
| Item | Detail |
|---|---|
| Beneficial Ownership | 104,840 shares/units beneficially owned (includes 82,044 shares held directly and 22,796 2022–2024 PSUs at target that vested 12/31/24 but unsettled as of record date); <1% of outstanding . |
| Outstanding Equity (select) | 2024 RSUs 14,959 (vest 1/1/2027); 2024 PSUs target 29,918; 2023 RSUs 15,151 (vest 1/1/2026); 2023 PSUs target 30,302; IPO RSUs two tranches of 100,000 each; Options 400,000 at $15.00 exercise price (vesting 50% on 1/12/2026 and 50% on 1/12/2027) . |
| Ownership Guidelines | CEO required to hold SKWD stock equal to 5x base salary; executives must retain 50% of after-tax shares until compliant (unvested RSUs count; unearned PSUs do not) . |
| Hedging/Pledging | Prohibited for executives and directors under the Insider Trading Policy and Corporate Governance Guidelines; no margin accounts or short sales . |
| Year-end Reference Price | Company used $50.54 (12/31/24) for award value tables . |
Vesting supply considerations:
- Near-term PSU settlement (2022–2024 relative GTBVPS) expected May 2025 (PEO target 22,796), and larger RSU/Option cliffs in 2026–2027 could modestly increase sellable supply windows .
Employment Terms
| Provision | Summary (Andrew Robinson) |
|---|---|
| Employment Agreement | At-will; base salary (2024: $900k) and performance-based bonus eligibility . |
| Severance (no CIC) | If terminated without cause or resigns for good reason: 1x base salary lump sum; up to 1 year health premiums; pro-rated target bonus for year of termination; any earned prior-year bonus; acceleration of time-based equity . |
| Severance (within 12 months after CIC) | Above benefits plus accelerated vesting of performance-based equity at not less than target (Board good-faith valuation); no single-trigger vesting in equity plans . |
| Restrictive Covenants | Non-compete 12 months (reduced to 6 months if within 12 months after CIC or disability); non-solicit employees/customers 1 year; confidentiality ongoing . |
| 280G | “Best net” cutback; no excise tax gross-up . |
| Definitions | “Cause” and “Good Reason” defined (incl. material diminution in pay/authority, involuntary relocation, material breach, removal from Board without cause) . |
Potential payments as of 12/31/2024 (illustrative, using $50.54 stock price):
- Involuntary or Good Reason termination pre-CIC: $4,724,751 total (incl. $900,000 cash severance; $1,125,000 pro-rated target bonus; $2,673,869 equity acceleration; $25,882 benefits) .
- In connection with CIC: $33,687,316 total (incl. $900,000 cash severance; $1,125,000 pro-rated target bonus; $31,336,434 equity acceleration; $25,882 benefits) .
- Death/Disability: $32,761,434 total (incl. $1,125,000 pro-rated target bonus; $31,336,434 equity acceleration) .
Board Governance
- Role and independence: Robinson serves as combined Chairman and CEO; he is not independent under Nasdaq rules; all committees comprise independent directors .
- Lead Independent Director: Anthony J. Kuczinski presides over executive sessions, interfaces with management, and oversees areas where the Chair may be conflicted, mitigating combined-role governance concerns .
- Board service: Class II director (re-elected in 2024 to term ending 2027); Board met 8 times in 2024, with all directors attending at least 75% .
- Committee roles: Robinson is not listed as a member of Audit, Compensation, Nominating & Governance, Risk, or Investment Committees, preserving committee independence .
Director compensation context: Non-employee directors receive retainers and annual RSU grants; non-independent (management) directors do not receive board fees; director stock ownership requirement is 5x retainer; hedging/pledging prohibited .
Say-on-Pay & Shareholder Feedback
- 2025 Say-on-Pay support was strong: For 35,238,948; Against 329,149; Abstain 6,004; broker non-votes 1,456,836 .
- Say-on-Frequency: “Every one year” selected decisively (34,818,977 votes) .
- Auditor ratification: EY ratified for FY2025 (37,017,459 For; 10,733 Against; 2,744 Abstain) .
Compensation Peer Group and Committee Process
- Compensation Committee (independent directors) oversees CEO/NEO pay; uses FW Cook as independent advisor; emphasizes variable, performance-linked pay .
- Reference group used for 2024 decisions included: AMERISAFE, Argo Group, Employers Holdings, Global Indemnity, James River Group, Kinsale, Palomar, ProAssurance, RLI, Safety Insurance, SiriusPoint, Tiptee, Trisura, United Fire Group, Universal Insurance .
- Positive pay practices: Dodd-Frank-compliant clawback; no hedging/pledging; capped PSU payouts; no option repricing without shareholder approval; no tax gross-ups; stock ownership guidelines for executives and directors .
Performance & Track Record
| Metric | 2023 | 2024 |
|---|---|---|
| SKWD Total Shareholder Return | 177.38 | 264.61 |
| Peer Group TSR | 103.37 | 128.30 |
| Net Income ($M) | 85.98 | 118.83 |
| Internal Combined Ratio | 91.6% | 91.6% |
| GWP Growth | — | 19.4% |
| ROE | 15.9% | 16.3% |
| A.M. Best Rating | — | Upgraded to “A (Excellent)” |
Achievements: launched five new lines; consistent sub-93% internal CR; IPO in Jan 2023 with sustained profitable growth (“Rule Our Niche” strategy) .
Equity Award Vesting Schedules and Potential Selling Pressure
| Award | Amount (PEO) | Vesting/Timing | Notes |
|---|---|---|---|
| 2022–2024 PSUs (relative GTBVPS) | 22,796 target | Eligible 12/31/2024; settlement anticipated May 2025 | Settlement timing may add share supply near-term. |
| 2023 IPO RSUs (two tranches) | 100,000 each | 50% vest 1/12/2025 & 1/12/2026 (first tranche); 50% 1/12/2026 & 1/12/2027 (second tranche) | Staggered vesting. |
| 2023 NQSOs | 400,000 @ $15.00 | 50% vest 1/12/2026; 50% 1/12/2027 | Options referenced against $50.54 YE price in tables . |
| 2024 RSUs | 14,959 | 1/1/2027 | Time-based. |
| 2024 PSUs (CR and relative GAAP BVPS) | 29,918 target | Perf period 2024–2026; vest 1/1/2027 subject to results | Capped at 150%. |
Employment Terms (Quantitative Illustration at 12/31/2024)
| Scenario | Cash Severance | Pro-rated Target Bonus | Equity Acceleration | Health/Benefits | Total |
|---|---|---|---|---|---|
| Involuntary/Good Reason (pre-CIC) | 900,000 | 1,125,000 | 2,673,869 | 25,882 | 4,724,751 |
| Involuntary/Good Reason (with CIC) | 900,000 | 1,125,000 | 31,336,434 | 25,882 | 33,687,316 |
| Death/Disability | — | 1,125,000 | 31,336,434 | — | 32,761,434 |
Investment Implications
- Pay-for-performance alignment: Variable pay mix rose (2024 target LTI up to $1.5M; STIP paid 140% on profitable growth), with PSU metrics tied to underwriting discipline (CR) and capital compounding (relative GAAP BVPS); TSR outperformed peers, supporting program credibility .
- Supply windows: PSU settlement in May 2025 and larger 2026–2027 RSU/option cliffs could create episodic selling pressure; however, ownership and retention guidelines plus staggered schedules mitigate concentration risk .
- Governance risk mitigants: Combined CEO/Chair structure offset by a strong Lead Independent Director, fully independent committees, clawback policy, prohibition on hedging/pledging, and double-trigger CIC equity vesting (no single-trigger; no tax gross-ups) .
- Retention and transition risk: CEO severance is a moderate 1x base plus pro-rated bonus and time-based equity acceleration (target-level performance equity only on double-trigger), which balances retention and shareholder alignment .
- Shareholder support: Overwhelming Say-on-Pay approval and annual frequency signal investor endorsement of compensation design and performance alignment .