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Skyward Specialty Insurance Group, Inc.·4

Feb 27, 4:05 PM ET

Schmitt Thomas N 4

4 · Skyward Specialty Insurance Group, Inc. · Filed Feb 27, 2026

Research Summary

AI-generated summary of this filing

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.

Insider Transaction Report

Form 4
Period: 2026-02-25
Skyward Specialty Insurance Group, Inc.SKWD
Schmitt Thomas N
CPO, Skyward Group
Transactions
  • Exercise/Conversion

    Common Stock

    [F1]
    2026-02-25+2,929→ 17,676 total
  • Tax Payment

    Common Stock

    [F2]
    2026-02-26$45.89/sh−1,153$52,911→ 16,523 total
  • Exercise/Conversion

    2023 LTIP - PSUs

    [F3][F4]
    2026-02-25−2,525→ 0 total
    → Common Stock (2,525 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 LTIP - PSUs

    [F8]
    2026-02-25+1,442→ 1,442 total
    → Common Stock (1,442 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 2,525 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 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.
Signature
/s/ Stacy E. Skelton, Attorney-in-Fact|2026-02-27

Documents

1 file
  • 4
    form4-02272026_040208.xmlPrimary