Stuart P. Winston
Executive Vice President, Chief Underwriting Officer at KNSL
Executive
About Stuart P. Winston
Executive Vice President and Chief Underwriting Officer at Kinsale Capital Group, Inc. (promoted October 23, 2025); previously Senior Vice President and Chief Underwriting Officer effective March 1, 2024, and before that Senior Vice President, Underwriting overseeing construction, excess casualty, general casualty, and small business divisions; joined Kinsale in 2010 after underwriting roles at James River Insurance Company . Holds a B.A. in Managerial Economics (Hampden-Sydney College) and professional designations ARe and CPCU from The Institutes . Company performance under the senior leadership team includes strong underwriting profitability and growth: combined ratio 78.5% (2022), 75.4% (2023), 76.4% (2024); operating ROE 25.0% (2022), 31.8% (2023), 29.2% (2024); gross written premiums +42.3% (2023) and +19.2% (2024); net operating earnings $180.4mm (2022), $291.4mm (2023), $374.8mm (2024) . Long-term shareholder returns since IPO are robust, with 2024 TSR of 39.1% and compounded annual gain of 49.7% from 2016–2024 .
Past Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| Kinsale Capital Group, Inc. | EVP, Chief Underwriting Officer | Oct 23, 2025–present | Leads underwriting operations; positioned to deliver continued profit and growth per CEO statement . |
| Kinsale Capital Group, Inc. | SVP, Chief Underwriting Officer | Mar 1, 2024–Oct 23, 2025 | Led underwriting operations; promotion from SVP Underwriting . |
| Kinsale Capital Group, Inc. | SVP, Underwriting | 2022–Feb 29, 2024 | Oversaw construction, excess casualty, general casualty, small business underwriting divisions . |
| Kinsale Capital Group, Inc. | Various underwriting leadership roles | 2010–2022 | Positions of increasing responsibility building underwriting capabilities . |
External Roles
| Organization | Role | Years | Strategic Impact |
|---|---|---|---|
| James River Insurance Company | Underwriting roles | Prior to 2010 | Foundation of underwriting expertise prior to joining Kinsale . |
Fixed Compensation
- The Company’s executive compensation program comprises base salary, annual cash incentive, equity awards, and benefits, designed for alignment with profitability, growth, and operational excellence; compensation determinations are overseen by the Compensation, Nominating & Corporate Governance Committee (CNCG) . Specific base salary/bonus figures for Mr. Winston are not disclosed in the proxy; Kinsale did not retain a compensation consultant in fiscal 2024 but engaged Semler Brossy in 2025 for the new Omnibus Incentive Plan .
Performance Compensation
Most important measures used to determine executive compensation in 2024 :
| Metric | Definition/Notes |
|---|---|
| Actual underwriting profit | Company-defined non-GAAP; see CD&A for calculation . |
| Combined ratio | Loss ratio + expense ratio; under 100% indicates underwriting profit . |
| Operating return on equity | Non-GAAP; net operating earnings / average equity . |
Company performance on compensation-linked metrics:
| Metric | FY 2022 | FY 2023 | FY 2024 |
|---|---|---|---|
| Underwriting income ($USD Thousands) | $175,488 | $270,374 | $325,881 |
| Net operating earnings ($USD Thousands) | $180,363 | $291,400 | $374,771 |
| Combined ratio (%) | 78.5% | 75.4% | 76.4% |
| Operating ROE (%) | 25.0% | 31.8% | 29.2% |
Notes:
- Annual cash bonuses at Kinsale are discretionary and tied to overall corporate performance per the CD&A; specific plan targets/weightings and Mr. Winston’s payouts are not disclosed .
Equity Ownership & Alignment
| Policy/Plan | Provision | Implication |
|---|---|---|
| Insider trading policy | Prohibits hedging, margin accounts, short sales, and pledging of company common stock . | Reduces misalignment risk and leverage-related sell pressure. |
| Executive stock ownership guidelines | Multiples: CEO 5x, CFO 3x, COO 3x, President 3x; executives must retain at least 50% of net shares until requirements achieved; all executive officers subject to the policy were in compliance as of Dec 31, 2024 . | Encourages long-term equity exposure; role-specific multiples disclosed (CUO not enumerated). |
| 2016 Omnibus Incentive Plan | RSAs vest 25% annually over 4 years; IPO options vest in four equal installments, 10-year term, post-termination exercise windows; acceleration upon death/disability; forfeiture for cause . | Time-based vesting supports retention; limited option exercise window discourages timing games. |
| 2025 Omnibus Incentive Plan | Approved May 22, 2025; replaces 2016 plan; share reserve 860,500 plus forfeitures from 2016 awards; plan authorizes options, RS, RSUs, other awards; CNCG administers . | Fresh equity capacity sustains ongoing incentives, subject to Board oversight. |
- Recent Form 4 data for Mr. Winston could not be retrieved due to data source authorization error; attempted query for 2022–2025 filings filtered by “Winston” at KNSL (API returned 401 Unauthorized). We will monitor for insider transactions for vesting/withholding-related sell patterns.
Employment Terms
- No employment agreement is disclosed for Mr. Winston; Kinsale reports having an employment agreement only with the CEO (Kehoe) and no employment agreements with other NEOs; general severance and change-in-control terms are not presented for Mr. Winston .
- Equity awards vest per plan terms; unvested restricted stock fully vests upon death/disability under the plan .
Performance & Track Record
| Indicator | FY 2022 | FY 2023 | FY 2024 |
|---|---|---|---|
| Gross written premiums ($USD Thousands) | $1,102,092 | $1,568,815 | $1,870,341 |
| Net income ($USD Thousands) | $159,114 | $308,093 | $414,843 |
| Return on equity (%) | 22.0% | 33.6% | 32.3% |
- Leadership continuity: Winston’s promotions in 2024 and 2025 signal succession depth and underwriting leadership emphasis as Haney transitions and retires in 2026; CEO highlighted Winston’s “deep underwriting acumen” and “track record of management success” .
- Shareholder outcomes: Kinsale 2024 TSR 39.1%; long-term compounded annual gain 49.7% since IPO .
Governance & Shareholder Feedback
- Say-on-Pay approval: ~96% support at 2024 Annual Meeting .
- CNCG responsibilities: oversees executive pay, equity plans; engaged Semler Brossy in 2025 for Omnibus Plan development .
- Risk assessment: CNCG concluded the program does not encourage unnecessary/excessive risk-taking; bonuses tied to company performance; equity aligns executives with stockholders .
Investment Implications
- Alignment: Anti-hedging/anti-pledging policy and retention expectations promote long-term alignment; equity grants with four-year vesting support retention and may constrain near-term selling pressure to tax-withholding events .
- Execution risk and leverage: CUO role central to underwriting discipline; company-level improvements in combined ratio and sustained operating ROE suggest disciplined risk selection and expense control, supporting pay-for-performance continuity under underwriting-profit and combined-ratio metrics .
- Transition: Winston’s elevation to EVP CUO during Haney’s transition reduces leadership gap in underwriting, with CEO’s stated confidence mitigating execution risk in 2025–2026 .
- Data watchouts: Individual compensation, ownership, and Form 4 activity for Winston are not disclosed/accessible in proxies and could not be pulled programmatically today; monitor future DEF 14A/8-K filings and Form 4s to assess vesting schedules, grants, and any insider activity to refine views on selling pressure and retention risk .