Duffy Sean W 4
4 · Skyward Specialty Insurance Group, Inc. · Filed May 8, 2026
Research Summary
AI-generated summary of this filing
Skyward Specialty (SKWD) EVP Sean Duffy Exercises PSUs, Shares Withheld
What Happened
Sean W. Duffy, EVP & Chief Claims Officer of Skyward Specialty (SKWD), had performance share units (PSUs) settle on May 6, 2026. The PSUs converted into 3,805 shares (exercise/conversion), the issuer withheld 1,671 of those shares to satisfy tax withholding (proceeds = $72,989), and the original PSU derivative award (2,861 PSUs) was removed upon settlement. Net increase to his share position from the settlement was 3,805 − 1,671 = 2,134 shares.
Key Details
- Transaction date: May 6, 2026; Form filed May 8, 2026 (appears timely).
- Conversion/exercise: 3,805 shares acquired via settlement of PSUs (transaction code M) at $0 exercise price.
- Tax withholding: 1,671 shares withheld (transaction code F) at $43.68 per share = $72,989. This withholding was mandated by the issuer (not a discretionary sale).
- Derivative removal: 2,861 PSUs (original award) reported as converted/removed upon settlement.
- Footnotes: The 2,861 PSUs were awarded Feb 27, 2023, subject to 2023–2025 performance; they fully vested and settled following Compensation Committee certification. Each PSU equals one share; the vested payout implied a performance multiplier of roughly 133% (3,805/2,861).
- Shares owned after transaction: not specified in the excerpt; net newly acquired shares from this settlement = ~2,134.
Context
PSU settlements and issuer-mandated share withholding for taxes are routine compensation events and do not necessarily reflect a deliberate open‑market sale by the insider. Here, the filing documents a performance-based award that vested and converted to common stock, with a portion withheld to satisfy tax obligations.
Insider Transaction Report
- Exercise/Conversion
Common Stock
[F1]2026-05-06+3,805→ 21,768 total - Tax Payment
Common Stock
[F2]2026-05-06$43.68/sh−1,671$72,989→ 20,097 total - Exercise/Conversion
2023 LTIP - PSUs
[F3][F4]2026-05-06−2,861→ 0 total→ Common Stock (2,861 underlying)
Footnotes (4)
- [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.