Schmitt Thomas N 4

4 · Skyward Specialty Insurance Group, Inc. · Filed May 8, 2026

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Updated May 8, 2026

Skyward (SKWD) CPO Thomas Schmitt Receives PSU Shares

What Happened

Thomas N. Schmitt, Chief Product Officer of Skyward Specialty Insurance Group (SKWD), had performance share units (PSUs) settle on May 6, 2026. The filing shows 3,358 shares were issued upon settlement (reported as conversion/exercise, code M). To satisfy tax withholding, 1,322 shares were withheld and disposed at $43.68/share, generating $57,745 (reported under code F). After withholding, Schmitt received a net 2,036 shares (3,358 issued minus 1,322 withheld). The filing also references 2,525 PSUs awarded on Feb 27, 2023 that vested and were settled (see footnotes).

Key Details

Transaction date: 2026-05-06; filing date: 2026-05-08 (no late filing indicated).
Shares issued on settlement: 3,358 (code M, $0 per share reported for issuance).
Shares withheld for taxes: 1,322 sold/withheld at $43.68 each, totaling $57,745 (code F; withholding mandated by issuer).
Net shares received (implied): 2,036 shares.
Shares owned after transaction: Not reported in the Form 4 provided.
Relevant footnotes:
- F1/F3: PSUs convert 1:1 into shares upon settlement.
- F2: The 1,322-share disposition was mandatory withholding to cover taxes (not a discretionary sale).
- F4: The 2,525-PSU award from Feb 27, 2023 was subject to performance through 2025, fully vested as of Dec 31, 2025 and settled upon board certification.

Context

These were PSUs (performance-based equity awards) that vested and were settled into common stock; the transaction is not an open-market purchase or voluntary sale but a routine settlement and tax withholding.
Withholding to cover taxes is common and typically does not signal insider intent to sell additional shares.

Form 4

Period: 2026-05-06

CPO, Skyward Group

Transactions

Exercise/Conversion
Common Stock
[F1]
2026-05-06+3,358→ 19,881 total
Tax Payment
Common Stock
[F2]
2026-05-06$43.68/sh−1,322$57,745→ 18,559 total
Exercise/Conversion
2023 LTIP - PSUs
[F3][F4]
2026-05-06−2,525→ 0 total
→ Common Stock (2,525 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 2,525 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.

Signature

/s/ Stacy E. Skelton, Attorney-in-Fact|2026-05-08

1 file