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Skyward Specialty (SKWD) EVP reports PSU vesting, new RSU/PSU grants and tax share disposition

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(Neutral)
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(Neutral)
Form Type
4

Rhea-AI Filing Summary

Skyward Specialty Insurance Group EVP & Chief Claims Officer Sean W. Duffy reported equity award activity and a related tax-withholding share disposition. On February 25, 2026, 2,861 performance share units granted in 2023 fully vested after meeting performance criteria and were settled into an equal number of common shares. On the same date, he received new equity awards: 1,442 RSUs vesting on January 1, 2029, 1,442 PSUs that can vest from 0% to 200% of target and fully vest on December 31, 2028, and 4,326 RSUs with 50% vesting on January 1, 2029 and 50% on January 1, 2030. A related Form 4 entry shows 1,391 common shares were disposed of at $45.89 per share on February 26, 2026 to satisfy tax withholding obligations mandated by the company, not as a discretionary trade, leaving him with 17,963 common shares held directly.

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Insider Duffy Sean W
Role EVP & Chief Claims Officer
Type Security Shares Price Value
Tax Withholding Common Stock 1,391 $45.89 $64K
Exercise 2023 LTIP - PSUs 2,861 $0.00 --
Grant/Award 2026 LTIP - RSUs 1,442 $0.00 --
Grant/Award 2026 LTIP - PSUs 1,442 $0.00 --
Grant/Award 2026 Bright Future - RSUs 4,326 $0.00 --
Exercise Common Stock 3,318 $0.00 --
Holdings After Transaction: Common Stock — 17,963 shares (Direct); 2023 LTIP - PSUs — 0 shares (Direct); 2026 LTIP - RSUs — 1,442 shares (Direct); 2026 LTIP - PSUs — 1,442 shares (Direct); 2026 Bright Future - RSUs — 4,326 shares (Direct)
Footnotes (1)
  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. 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. Each PSU represents the right to receive one share of the Issuer's Common Stock upon settlement. On February 27, 2023, the Reporting Person was awarded 2,861 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. Each Restricted Stock Unit ("RSU") represents the right to receive one share of the Issuer's Common Stock upon settlement. 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. 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. On February 25, 2026, the Reporting Person was granted an RSU Award in the amount of 4,326 RSUs. Subject to the terms of the RSU Agreement and the Reporting Person's continuous service through the vesting dates, 50% of the RSUs shall vest on January 1, 2029 and the remaining 50% of the RSUs will vest on January 1, 2030.
Form 4 Insider Transactions: What Each Field Means →
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
Estimated average burden
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*
Duffy Sean W
(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)
EVP & Chief Claims Officer
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 3,318(1) A $0 19,354 D
Common Stock 02/26/2026 F(2) 1,391 D $45.89 17,963 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 2,861 (4) (4) Common Stock 2,861 $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 Bright Future - RSUs (5) 02/25/2026 A 4,326 (8) (8) Common Stock 4,326 $0 4,326 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 2,861 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 an RSU Award in the amount of 4,326 RSUs. Subject to the terms of the RSU Agreement and the Reporting Person's continuous service through the vesting dates, 50% of the RSUs shall vest on January 1, 2029 and the remaining 50% of the RSUs will vest on January 1, 2030.
/s/ Stacy E. Skelton, Attorney-in-Fact 02/27/2026
** Signature of Reporting Person Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

Source: View Original Filing on SEC EDGAR

FAQ

What did SKWD executive Sean W. Duffy report on this Form 4?

Sean W. Duffy reported vesting and settlement of 2,861 performance share units into common stock, several new RSU and PSU grants dated February 25, 2026, and a company-mandated share disposition to cover tax withholding obligations tied to the PSU settlement.

How many Skyward Specialty (SKWD) shares were used to cover taxes?

The filing shows 1,391 shares of Skyward Specialty common stock were disposed of at $45.89 per share on February 26, 2026 to satisfy tax withholding obligations related to PSU vesting, a disposition mandated by the issuer rather than a discretionary sale by Duffy.

What new RSU awards did SKWD grant to Sean W. Duffy?

On February 25, 2026, Duffy received 1,442 RSUs vesting 100% on January 1, 2029, and 4,326 “Bright Future” RSUs, with 50% scheduled to vest on January 1, 2029 and the remaining 50% on January 1, 2030, subject to continuous service.

What new PSU award did Skyward Specialty (SKWD) grant in 2026?

On February 25, 2026, Duffy was granted 1,442 performance share units, each equivalent to one share of common stock. The actual vesting can range from 0% to 200% of target based on performance conditions, with full vesting on December 31, 2028.

How many SKWD common shares does Sean W. Duffy hold after these transactions?

After the reported transactions, Duffy directly owns 17,963 shares of Skyward Specialty common stock. This balance reflects PSU settlement into shares and a tax-withholding disposition but does not include unvested RSU or PSU awards, which remain as derivative holdings.

What were the terms of Sean W. Duffy’s 2023 PSU award at SKWD?

Duffy was awarded 2,861 PSUs on February 27, 2023, subject to performance from January 1, 2023 through December 31, 2025. The vesting range was 0% to 150% of target; the award fully vested on December 31, 2025 and settled after Compensation Committee certification.