Skyward CPO reports PSU vesting, tax withholding

Skyward Specialty Insurance Group CPO Thomas N. Schmitt reported multiple equity award events and related tax withholding.

Rhea-AI Filing Summary

Skyward Specialty Insurance Group CPO Thomas N. Schmitt reported multiple equity award events and related tax withholding. He acquired common stock through settlement of previously granted performance share units (PSUs), and received new 2026 long-term incentive awards in the form of restricted stock units (RSUs) and PSUs, each covering 1,442 units at a stated price of $0.00 per unit.

To cover tax obligations from the PSU vesting and settlement, 1,153 shares of common stock were withheld at $45.89 per share in a disposition mandated by the issuer and not a discretionary sale. After these transactions, Schmitt directly owned 16,523 shares of common stock.

Insider Trade Summary

2,525 shares exercised/converted

Exercise 6 txns

Insider Schmitt Thomas N

Role CPO, Skyward Group

Type	Security	Shares	Price	Value
Exercise Price or Tax Liability	Common Stock	1,153	$45.89	$53K
Exercise	2023 LTIP - PSUs	2,525	$0.00	$0.00
Grant/Award	2026 LTIP - RSUs	1,442	$0.00	$0.00
Grant/Award	2026 LTIP - PSUs	1,442	$0.00	$0.00
Grant/Award	2026 LTIP - PSUs	1,442	$0.00	$0.00
Exercise	Common Stock	2,929	$0.00	$0.00

Holdings After Transaction: 2023 LTIP - PSUs — 0 contracts (Direct); 2026 LTIP - RSUs — 1,442 contracts (Direct); 2026 LTIP - PSUs — 2,884 contracts (Direct); Common Stock — 16,523 shares (Direct)

Footnotes (8)

1. 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.
2. 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.
3. F3. Each PSU represents the right to receive one share of the Issuer's Common Stock upon settlement.
4. 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.
5. F5. Each Restricted Stock Unit ("RSU") represents the right to receive one share of the Issuer's Common Stock upon settlement.
6. 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.
7. 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.
8. 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.

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

What did SKWD executive Thomas N. Schmitt report in this Form 4?

Thomas N. Schmitt reported PSU vesting, new RSU and PSU equity grants, and tax-related share withholding. Previously awarded PSUs converted into common stock, and new 2026 long-term incentive awards were granted, alongside shares withheld to satisfy tax obligations tied to these settlements.

How many shares were withheld for taxes in the SKWD Form 4?

The Form 4 shows 1,153 shares of Skyward Specialty common stock withheld at $45.89 per share. This disposition covered tax withholding obligations from PSU vesting and settlement and, according to the disclosure, was mandated by the issuer rather than initiated at the executive’s discretion.

What performance-based awards vested for SKWD CPO Thomas N. Schmitt?

Previously granted PSUs awarded on February 27, 2023 fully vested on December 31, 2025 after achieving specified performance criteria. Each PSU is equivalent to one share of common stock, and the vested units were settled into shares, as reflected in the reported derivative exercise transaction.

What new RSU award did SKWD grant to Thomas N. Schmitt?

On February 25, 2026, Schmitt received an RSU award covering 1,442 RSUs. Each RSU converts into one share of common stock upon settlement, with 100% of the RSUs scheduled to vest on January 1, 2029, contingent on his continuous service through the vesting date.

What new PSU awards did SKWD grant to Thomas N. Schmitt?

On February 25, 2026, Schmitt was granted PSUs where each unit equals one share of common stock. The number of PSUs that ultimately vest can range from 0% to 200% of the 1,442-unit amount shown, based on performance targets through December 31, 2028.

How many SKWD shares does Thomas N. Schmitt own after these transactions?

Following the PSU settlement, RSU and PSU grants, and tax withholding, the Form 4 reports that Thomas N. Schmitt directly owned 16,523 shares of Skyward Specialty common stock. This figure reflects his direct ownership immediately after the reported transactions were completed.

Was the SKWD share disposition a discretionary sale by Thomas N. Schmitt?

The disposition was not discretionary. Footnotes state the 1,153 shares withheld were used to satisfy tax withholding obligations from PSU vesting and settlement, and that this transaction was mandated by the issuer rather than initiated at Schmitt’s personal discretion.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Accepted by SEC EDGAR 02/27/2026 - 04:05 PM Learn about SEC filing dates

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
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hours per response:			0.5

Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Schmitt Thomas N

(Last) (First) (Middle)

800 GESSNER

SUITE 600

(Street)

HOUSTON TX 77024

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
Skyward Specialty Insurance Group, Inc. [ SKWD ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	CPO, Skyward Group

3. Date of Earliest Transaction (Month/Day/Year)
02/25/2026

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price
Common Stock	02/25/2026		M		2,929(1)	A	$0	17,676	D
Common Stock	02/26/2026		F(2)		1,153	D	$45.89	16,523	D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares
2023 LTIP - PSUs	(3)	02/25/2026		M			2,525	(4)	(4)	Common Stock	2,525	$0	0	D
2026 LTIP - RSUs	(5)	02/25/2026		A		1,442		(6)	(6)	Common Stock	1,442	$0	1,442	D
2026 LTIP - PSUs	(7)	02/25/2026		A		1,442		(7)	(7)	Common Stock	1,442	$0	1,442	D
2026 LTIP - PSUs	(8)	02/25/2026		A		1,442		(8)	(8)	Common Stock	1,442	$0	1,442	D

Explanation of Responses:

1. 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.

2. 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.

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

4. 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.

5. Each Restricted Stock Unit ("RSU") represents the right to receive one share of the Issuer's Common Stock upon settlement.

6. 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.

7. 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.

8. 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.

	/s/ Stacy E. Skelton, Attorney-in-Fact	02/27/2026
	** Signature of Reporting Person	Date
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