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Skyward Specialty (SKWD) EVP settles PSUs with mandatory tax withholding

Filing Impact
(Neutral)
Filing Sentiment
(Neutral)
Form Type
4

Rhea-AI Filing Summary

Skyward Specialty Insurance Group EVP Sean W. Duffy reported equity compensation activity tied to performance share awards. On May 6, 2026, 2,861 Performance Share Units (PSUs) granted on February 27, 2023, fully vested based on performance from January 1, 2023 through December 31, 2025 and were settled in an equal number of common shares.

To cover related tax withholding obligations, 1,671 common shares were withheld, a disposition that the company mandated and that was not a discretionary market transaction. After these transactions, Duffy directly held 21,768 shares of Skyward Specialty Insurance Group common stock.

Positive

  • None.

Negative

  • None.
Insider Duffy Sean W
Role EVP & Chief Claims Officer
Type Security Shares Price Value
Exercise 2023 LTIP - PSUs 2,861 $0.00 --
Exercise Common Stock 3,805 $0.00 --
Tax Withholding Common Stock 1,671 $43.68 $73K
Holdings After Transaction: 2023 LTIP - PSUs — 0 shares (Direct, null); Common Stock — 21,768 shares (Direct, null)
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.
PSUs converted to common stock 2,861 units 2023 PSUs covering performance from January 1, 2023 to December 31, 2025
Shares withheld for taxes 1,671 shares at $43.68 Common stock withheld on May 6, 2026 to cover tax obligations on PSU vesting
Post-transaction share holdings 21,768 shares Direct ownership of Skyward Specialty common stock after May 6, 2026 transactions
Original PSU award size 2,861 PSUs Awarded on February 27, 2023 under 2023 LTIP with performance-based vesting
PSU vesting range 0%–150% Potential vesting outcome of 2023 PSUs based on performance over 2023–2025 period
Performance Share Units ("PSUs") financial
"Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Performance Share Units ("PSUs")"
tax withholding obligations financial
"shares withheld to cover tax withholding obligations in connection with the vesting and settlement of the PSUs"
vesting and settlement financial
"in connection with the vesting and settlement of the PSUs listed in Line I of Table II"
Compensation Committee of the Board of Directors financial
"settled upon certification by the Compensation Committee of the Board of Directors"
2023 LTIP - PSUs financial
"security_title": "2023 LTIP - PSUs""
Form 4 Insider Transactions: What Each Field Means →
SEC Form 4
FORM 4UNITED 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
X
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 TEXAS 77024
(City)(State)(Zip)
UNITED STATES
(Country)		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)
Director10% Owner
XOfficer (give title below)Other (specify below)
EVP & Chief Claims Officer
2a. Foreign Trading Symbol
3. Date of Earliest Transaction (Month/Day/Year)
05/06/2026		6. Individual or Joint/Group Filing (Check Applicable Line)
XForm filed by One Reporting Person
Form filed by More than One Reporting Person
4. If Amendment, Date of Original Filed (Month/Day/Year)

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)
CodeVAmount(A) or (D)Price
Common Stock05/06/2026M3,805(1)A$021,768D
Common Stock05/06/2026F(2)1,671D$43.6820,097D
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)
CodeV(A)(D)Date ExercisableExpiration DateTitleAmount or Number of Shares
2023 LTIP - PSUs(3)05/06/2026M2,861 (4) (4)Common Stock2,861$00D
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.
/s/ Stacy E. Skelton, Attorney-in-Fact05/08/2026
** Signature of Reporting PersonDate
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.
* Form 4: SEC 1474 (03-26)

Source: View Original Filing on SEC EDGAR

FAQ

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

Sean W. Duffy reported PSU vesting and tax withholding. 2,861 Performance Share Units converted into common shares, and 1,671 shares were withheld to satisfy tax obligations. These events reflect equity compensation settlement rather than an open-market stock trade.

Were the SKWD Form 4 share dispositions by Sean W. Duffy open-market sales?

No, the disposition was for tax withholding. The 1,671 shares reported as disposed were withheld by the company to cover tax obligations tied to PSU vesting. The footnote states this withholding was mandated and not a discretionary transaction by Duffy.

How many Skyward Specialty (SKWD) shares does Sean W. Duffy hold after these transactions?

Sean W. Duffy holds 21,768 common shares after the transactions. This post-transaction balance reflects the vesting and settlement of PSUs and the related tax withholding, as reported in the Form 4 totals following the May 6, 2026 entries.

What are Performance Share Units (PSUs) in the SKWD Form 4 for Sean W. Duffy?

PSUs are performance-based equity awards. Each PSU gives the right to receive one SKWD common share upon settlement. Duffy’s 2,861 PSUs were tied to performance from January 1, 2023 through December 31, 2025 and fully vested based on certified results.

When did Sean W. Duffy’s 2023 SKWD PSUs vest and settle?

The 2023 PSUs fully vested on December 31, 2025. They were settled in common stock after the Compensation Committee certified performance for the January 1, 2023 to December 31, 2025 period, leading to the May 6, 2026 share transactions.

What performance period applied to Sean W. Duffy’s 2023 PSUs at Skyward Specialty (SKWD)?

The PSUs were tied to a three-year performance window. Performance criteria applied from January 1, 2023 through December 31, 2025. The number of PSUs eligible to vest could range from 0% to 150% of the original 2,861-unit award.