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Skyward Specialty (SKWD) CEO settles PSU grant, 7,930 shares withheld for taxes

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

Rhea-AI Filing Summary

Skyward Specialty Insurance Group Chairman & CEO Andrew S. Robinson settled a performance-based share award and had shares withheld for taxes. On May 6, 2026, he exercised 15,151 Performance Share Units (PSUs), each delivering one share of common stock upon settlement. In connection with this vesting, 7,930 shares of common stock were withheld at a price of $43.68 per share to satisfy tax withholding obligations, a disposition mandated by the company rather than a discretionary sale. Following these transactions, he holds 179,894 shares of common stock directly. The PSUs were originally granted on February 27, 2023 and vested based on performance criteria measured from January 1, 2023 through December 31, 2025, with settlement occurring after certification by the Compensation Committee.

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Insider Robinson Andrew S
Role Chairman & CEO, Skyward Group
Type Security Shares Price Value
Exercise 2023 LTIP - PSUs 15,151 $0.00 --
Exercise Common Stock 20,150 $0.00 --
Tax Withholding Common Stock 7,930 $43.68 $346K
Holdings After Transaction: 2023 LTIP - PSUs — 0 shares (Direct, null); Common Stock — 187,824 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 15,151 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.
Shares withheld for taxes 7,930 shares at $43.68 Common Stock withheld to cover tax obligations on May 6, 2026
PSUs exercised 15,151 PSUs 2023 LTIP Performance Share Units converting into common stock on May 6, 2026
Direct holdings after transaction 179,894 shares Common Stock directly owned by Andrew S. Robinson following Form 4 transactions
PSU grant date February 27, 2023 Award date for 15,151 PSUs under 2023 LTIP
PSU performance period end December 31, 2025 PSUs subject to performance criteria from January 1, 2023 through this date
Performance Share Units financial
"Represents the number of shares that were acquired by the Reporting Person in connection with the settlement of the Performance Share Units ("PSUs")"
Performance share units are a type of company stock award given to employees that depend on the company meeting specific goals or targets. If these goals are achieved, the employee receives shares or the value of shares; if not, they may receive little or no compensation. This aligns employees’ interests with the company's success and encourages performance that benefits investors.
PSUs financial
"On February 27, 2023, the Reporting Person was awarded 15,151 PSUs."
PSUs are company shares promised to employees or executives that only become actual stock if the business hits specific performance targets over a set period. For investors, PSUs matter because they link pay to measurable outcomes — similar to a conditional bonus that converts into ownership — which can influence management decisions, dilution of shares, and signals about confidence in future results.
tax withholding obligations financial
"shares withheld to cover tax withholding obligations in connection with the vesting and settlement of the PSUs"
Compensation Committee financial
"This award fully vested on December 31, 2025 and settled upon certification by the Compensation Committee of the Board of Directors."
A compensation committee is a group within a company's leadership responsible for setting and reviewing how much top executives and employees are paid, including salaries, bonuses, and benefits. It matters to investors because fair and effective pay decisions can influence a company's performance, leadership motivation, and overall governance, helping ensure that the company’s management is aligned with shareholders’ interests.
derivative security financial
"transaction_code_description": "Exercise or conversion of derivative security""
A derivative security is a financial contract whose value comes from the price or performance of something else, such as a stock, bond, commodity, or market index. For investors it acts like an insurance policy or a wager: it can be used to protect against losses, lock in prices, or amplify gains and losses, so it can change a portfolio’s risk and potential return without owning the underlying asset directly.
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
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*
Robinson Andrew S
(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)
XDirector10% Owner
XOfficer (give title below)Other (specify below)
Chairman & CEO, Skyward Group
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 Stock05/06/2026M20,150(1)A$0187,824D
Common Stock05/06/2026F(2)7,930D$43.68179,894D
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)05/06/2026M15,151 (4) (4)Common Stock15,151$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 15,151 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 did Skyward Specialty (SKWD) CEO Andrew Robinson report in this Form 4?

Andrew S. Robinson reported settlement of a performance share award and related tax withholding. He exercised 15,151 Performance Share Units into common stock and had 7,930 shares withheld to cover tax obligations, leaving him with 179,894 shares held directly after the transactions.

Were Andrew Robinson’s Skyward Specialty (SKWD) share transactions discretionary sales?

The filing states the disposition was not discretionary. Shares were withheld to satisfy tax withholding obligations tied to vesting and settlement of Performance Share Units, and this withholding was mandated by the issuer rather than initiated as an open-market sale by Robinson.

How many Skyward Specialty (SKWD) shares does Andrew Robinson own after these transactions?

After the reported Form 4 transactions, Andrew S. Robinson directly owns 179,894 shares of Skyward Specialty Insurance Group common stock. This figure reflects his position following the PSU settlement and the mandated tax-withholding share disposition on May 6, 2026.

What performance award was involved in Andrew Robinson’s Skyward Specialty (SKWD) Form 4?

The Form 4 involves a 2023 long-term incentive Performance Share Unit award of 15,151 PSUs. Each PSU converts into one share of common stock, contingent on performance criteria measured from January 1, 2023 through December 31, 2025, and settlement followed Compensation Committee certification.

When did Andrew Robinson’s Skyward Specialty (SKWD) PSUs vest and settle?

The PSUs were granted on February 27, 2023 and were subject to performance criteria from January 1, 2023 through December 31, 2025. The award fully vested on December 31, 2025 and then settled after certification by the Board’s Compensation Committee, leading to the May 6, 2026 share delivery.