Skyward Specialty Insurance Group, Inc.·4

Feb 27, 4:05 PM ET

Schmitt Thomas N 4

Research Summary

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Updated

Skyward (SKWD) CPO Thomas Schmitt Exercises Awards; Shares Withheld

What Happened

  • Thomas N. Schmitt, Chief People Officer of Skyward Specialty Insurance Group (SKWD), settled performance-based and restricted awards on Feb 25–26, 2026. The filing shows an exercise/conversion of derivative awards resulting in 2,929 shares acquired at $0. Separately, 1,153 shares were surrendered/withheld on Feb 26 at $45.89 per share to cover tax obligations (total withheld value reported as $52,911). The Form 4 also reports a prior PSU award of 2,525 units (from Feb 27, 2023) that vested and was reported as an exercise/conversion, and new grants on Feb 25, 2026 of one RSU award (1,442 RSUs) and two PSU awards (1,442 PSUs each).

Key Details

  • Transaction dates/prices:
    • Feb 25, 2026: Exercise/conversion (derivative) — 2,929 shares acquired @ $0.
    • Feb 25, 2026: Exercise/conversion (derivative) — 2,525 shares reported as disposed @ $0 (related to a 2023 PSU award that vested).
    • Feb 25, 2026: Grants/awards — three awards of 1,442 units each (one RSU, two PSUs) @ $0.
    • Feb 26, 2026: Tax withholding (F) — 1,153 shares disposed @ $45.89 = $52,911 (mandated withholding).
  • Shares owned after transaction: Not specified in the filing.
  • Notable footnotes:
    • PSUs and RSUs convert to one share per unit on settlement (footnotes F3, F5).
    • The 2,525 PSUs were awarded Feb 27, 2023 and fully vested Dec 31, 2025 (F4).
    • The new RSU vests 100% on Jan 1, 2029 (F6); the two new PSU awards vest Dec 31, 2028 subject to performance (F7, F8).
    • The 1,153-share disposition was a non-discretionary, issuer-mandated withholding to cover taxes (F2).
  • Filing timeliness: Form 4 was filed Feb 27, 2026 for transactions on Feb 25–26, 2026 — appears timely (Form 4s are due within two business days).

Context

  • These transactions are primarily settlements of compensation awards (PSUs/RSUs) and new grants, not open-market buying or discretionary selling. The 1,153-share "sale" was a tax withholding action mandated by the company, not a market disposition chosen by the officer.
  • PSUs are performance-based and may pay out 0%–150% (past award) or 0%–200% (new awards) of the target depending on results; RSUs vest based on continued service. These details matter for whether future shares may be issued if performance/service conditions are met.