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Skyward Specialty Insurance Group, Inc.·4

Feb 27, 4:05 PM ET

Duffy Sean W 4

Research Summary

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Updated

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.