Duffy Sean W 4
4 · Skyward Specialty Insurance Group, Inc. · Filed Feb 27, 2026
Research Summary
AI-generated summary of this filing
Skyward (SKWD) EVP Sean W. Duffy Exercises PSUs; Shares Withheld
What Happened
- Sean W. Duffy, EVP & Chief Claims Officer of Skyward Specialty Insurance Group (SKWD), had performance share units (PSUs) vest and convert to common stock and received new equity awards on Feb 25, 2026. The PSU settlement resulted in 3,318 shares issued to him. To cover tax withholding obligations, 1,391 of those shares were withheld/disposed on Feb 26 at $45.89 per share, producing $63,833 in value.
- In addition to the PSU settlement, the filing shows new equity grants on Feb 25, 2026: 1,442 RSUs (100% vest 1/1/2029), 1,442 PSUs (performance-based, 0–200% payout through 12/31/2028), and 4,326 RSUs (50% vest 1/1/2029, 50% vest 1/1/2030).
Key Details
- Transaction dates/prices:
- 2026-02-25: Conversion/exercise of PSUs — 3,318 shares acquired at $0.00 (settlement of PSUs).
- 2026-02-25: Original PSU award referenced — 2,861 PSUs (from 2023 award) settled (per footnotes).
- 2026-02-26: Mandatory tax withholding — 1,391 shares disposed at $45.89 each = $63,833.
- 2026-02-25: New awards granted — 1,442 RSUs, 1,442 PSUs, and 4,326 RSUs (all $0.00 per share grants).
- Shares owned after the transactions: not specified in the Form 4 excerpts provided.
- Notable footnotes:
- The 2,861 PSUs were awarded Feb 27, 2023 and vested for the 2023–2025 performance period; each PSU converts to one share on settlement (footnotes F3–F4).
- The disposition of 1,391 shares was a company-mandated withholding to cover taxes (non-discretionary; footnote F2).
- New RSU/PSU awards have multi-year vesting/performance schedules (footnotes F6–F8).
- Filing timeliness: Form 4 was filed Feb 27, 2026 for transactions on Feb 25–26, 2026 — appears timely (no late filing indicated).
Context
- This filing reflects routine equity compensation activity — vesting/settlement of PSUs and grant of new RSUs/PSUs — not an open-market investment decision. The share disposition was a tax-withholding action required by the company (not a voluntary sale).
- For investors: settlements that convert PSUs into shares can reflect the finalized performance payout (here the settled shares exceed the original 2,861 PSUs, implying a performance multiplier above 100%). New RSU/PSU grants are long-term compensation and vest over years, so they are more about retention and incentives than current buying/selling signals.
Insider Transaction Report
Form 4
Duffy Sean W
EVP & Chief Claims Officer
Transactions
- Exercise/Conversion
Common Stock
[F1]2026-02-25+3,318→ 19,354 total - Tax Payment
Common Stock
[F2]2026-02-26$45.89/sh−1,391$63,833→ 17,963 total - Exercise/Conversion
2023 LTIP - PSUs
[F3][F4]2026-02-25−2,861→ 0 total→ Common Stock (2,861 underlying) - Award
2026 LTIP - RSUs
[F5][F6]2026-02-25+1,442→ 1,442 total→ Common Stock (1,442 underlying) - Award
2026 LTIP - PSUs
[F7]2026-02-25+1,442→ 1,442 total→ Common Stock (1,442 underlying) - Award
2026 Bright Future - RSUs
[F5][F8]2026-02-25+4,326→ 4,326 total→ Common Stock (4,326 underlying)
Footnotes (8)
- [F1]Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Performance Share Units ("PSUs") listed in Line I of Table II.
- [F2]The disposition reported on this Form 4 represents shares withheld to cover tax withholding obligations in connection with the vesting and settlement of the PSUs listed in Line I of Table II. The disposition is mandated by the Issuer and does not represent a discretionary transaction by the Reporting Person.
- [F3]Each PSU represents the right to receive one share of the Issuer's Common Stock upon settlement.
- [F4]On February 27, 2023, the Reporting Person was awarded 2,861 PSUs. The PSUs are subject to obtaining specified performance criteria from January 1, 2023 through December 31, 2025. The number of PSUs subject to vest under this award can range from 0% to 150% of the amount shown. This award fully vested on December 31, 2025 and settled upon certification by the Compensation Committee of the Board of Directors.
- [F5]Each Restricted Stock Unit ("RSU") represents the right to receive one share of the Issuer's Common Stock upon settlement.
- [F6]On February 25, 2026, the Reporting Person was granted an RSU Award in the amount of 1,442 RSUs. Subject to the Reporting Person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2029.
- [F7]On February 25, 2026, the Reporting Person was granted 1,442 PSUs. Each PSU is equivalent to one share of the Issuer's Common Stock. The number of units subject to vest under this award can range from 0% to 200% of the amount shown based on the satisfaction of performance condition targets during the requisite service period. This award fully vests on December 31, 2028.
- [F8]On February 25, 2026, the Reporting Person was granted an RSU Award in the amount of 4,326 RSUs. Subject to the terms of the RSU Agreement and the Reporting Person's continuous service through the vesting dates, 50% of the RSUs shall vest on January 1, 2029 and the remaining 50% of the RSUs will vest on January 1, 2030.
Signature
/s/ Stacy E. Skelton, Attorney-in-Fact|2026-02-27