Thomas N. Schmitt - 12 Jan 2026 Form 4 Insider Report for Skyward Specialty Insurance Group, Inc. (SKWD)

Reporting relationship: CPO, Skyward Group
Issuer ticker: SKWD
Reported as of: 12 Jan 2026
Net transaction value: -$189,794
SEC form: 4
Accepted by SEC: 14 Jan 2026, 17:09:56 UTC
Prior SEC filing: 05 Jan 2026
Next SEC filing: 10 Feb 2026
Source filing: View source filing
Reporting owner signature: /s/ Stacy E. Skelton, Attorney-in-Fact

Key filing fact

Thomas N. Schmitt filed Form 4 for Skyward Specialty Insurance Group, Inc. (SKWD) on 14 Jan 2026.

Key facts

This page summarizes Thomas N. Schmitt's Form 4 filing for Skyward Specialty Insurance Group, Inc. (SKWD).
6 reported transactions and 2 derivative rows are listed below.
Accepted by SEC: 14 Jan 2026, 17:09.

Change

Previous filing in this sequence was filed on 05 Jan 2026.
Current net transaction value: -$189,794.

Research use

This tells you what this filing adds before you inspect full transaction and derivative tables.
You can trace every row back to the original SEC filing document.

Evidence

Filed on Form 4

Ownership activity is grounded in SEC Form 4 disclosures.

View source filing

Reporting Owners (1)

CIK 0001937316 Primary reporting owner

Schmitt Thomas N

Relationship: CPO, Skyward Group
Address: 800 GESSNER, SUITE 600, HOUSTON
Signature: /s/ Stacy E. Skelton, Attorney-in-Fact
Signature date: 14 Jan 2026

Reported non-derivative transactions

Shares, units, or other non-derivative securities reported in this filing.

SKWD transaction

Common Stock

Options Exercise

Transaction value: $0
Shares: +5,000
Change %: +44%
Price: $0.000000
Shares after: 16,480
Date: 12 Jan 2026
Ownership: Direct
Footnotes: F1

SKWD transaction

Common Stock

Tax liability

Transaction value: $99,069
Shares: -2,149
Change %: -13%
Price: $46.10
Shares after: 14,331
Date: 12 Jan 2026
Ownership: Direct
Footnotes: F2, F3

SKWD transaction

Common Stock

Options Exercise

Transaction value: $0
Shares: +5,000
Change %: +35%
Price: $0.000000
Shares after: 19,331
Date: 12 Jan 2026
Ownership: Direct
Footnotes: F1

SKWD transaction

Common Stock

Tax liability

Transaction value: $90,725
Shares: -1,968
Change %: -10%
Price: $46.10
Shares after: 17,363
Date: 12 Jan 2026
Ownership: Direct
Footnotes: F2, F3

Reported derivative securities

Options, warrants, convertible securities, or similar derivative positions disclosed in the filing.

SKWD transaction Derivative

2023 IPO RSU Grant (4-Year)

Options Exercise

Transaction value: $0
Shares: -5,000
Change %: -50%
Price: $0.000000
Shares after: 5,000
Date: 12 Jan 2026
Ownership: Direct
Underlying class: Common Stock
Underlying amount: 5,000
Exercise price
Footnotes: F4, F5

SKWD transaction Derivative

2023 IPO RSU Grant (3-Year)

Options Exercise

Transaction value: $0
Shares: -5,000
Change %: -100%
Price: $0.000000
Shares after: 0
Date: 12 Jan 2026
Ownership: Direct
Underlying class: Common Stock
Underlying amount: 5,000
Exercise price
Footnotes: F4, F6

^* marks a reported price that did not pass the local price check.

Additional SEC filing notes

Filing notes and footnotes

Explanation of responses 6 footnotes

Footnote 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.

Footnote 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 RSUs listed in Table II. The disposition is mandated by the Issuer and does not represent a discretionary transaction by the Reporting Person.

Footnote 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.

Footnote F4

Each RSU represents the right to receive one share of the Issuer's Common Stock upon settlement.

Footnote 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.

Footnote 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.