InsiderTrades

Form 4 for SKWD Skyward Specialty Insurance Group, Inc.

Accepted 2026-01-14 00:00:00 ET · period of report 2026-01-12 · accession 0001937316-26-000004 · SEC index · Original document

Summary rows

Aggregated the way they appear in lists: one row per insider, transaction code and security table.

X Filed Traded Ticker Insider Title Type Price Qty Owned ΔOwn Value
DM 2026-01-14 2026-01-12 SKWD Schmitt Thomas N CPO, Skyward Group M - OptEx $0.00 +10.0K 19.3K +107% $0
DM 2026-01-14 2026-01-12 SKWD Schmitt Thomas N CPO, Skyward Group F - Tax $46.10 -4,117 14.3K -22% -$189.8K
DM 2026-01-14 2026-01-12 SKWD Schmitt Thomas N CPO, Skyward Group M - OptEx $0.00 -10.0K 5,000 -67% $0

Purchase Sale Sale after option exercise All abbreviations

Every reported transaction

#TableSecurityDateCodeA/DSharesPriceOwned afterOwnExercise / expiryUnderlyingFootnotes
1 Common Common Stock 2026-01-12 M A 5,000 $0.00 16,480 D — — (F1) Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Restricted Stock Units ("RSUs") listed in Table II.
2 Common Common Stock 2026-01-12 M A 5,000 $0.00 19,331 D — — (F1) Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Restricted Stock Units ("RSUs") listed in Table II.
3 Common Common Stock 2026-01-12 F D 1,968 $46.10 17,363 D — — (F3) The number of shares withheld by the Issuer for the Reporting Owner was calculated using the closing price of the Issuer's Common Stock on the vesting date, January 12, 2026, pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Long Term Incentive Plan.
4 Common Common Stock 2026-01-12 F D 2,149 $46.10 14,331 D — — (F3) The number of shares withheld by the Issuer for the Reporting Owner was calculated using the closing price of the Issuer's Common Stock on the vesting date, January 12, 2026, pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Long Term Incentive Plan.
5 Derivative 2023 IPO RSU Grant (3-Year) 2026-01-12 M D 5,000 $0.00 0 D — · — to — 5,000 Common Stock (F4) Each RSU represents the right to receive one share of the Issuer's Common Stock upon settlement. (F6) On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 10,000 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2025, and the remaining 50% of the RSUs fully vested on January 12, 2026.
6 Derivative 2023 IPO RSU Grant (4-Year) 2026-01-12 M D 5,000 $0.00 5,000 D — · — to — 5,000 Common Stock (F4) Each RSU represents the right to receive one share of the Issuer's Common Stock upon settlement. (F5) On January 12, 2023, the Reporting Person was granted an RSU Award in the amount of 10,000 RSUs. Subject to the terms of the RSU Agreement, 50% of the RSUs fully vested on January 12, 2026. Subject to the Reporting Person's continuous service the remaining 50% of the RSUs will vest on January 12, 2027.