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Skyward Specialty (SKWD) CEO logs new PSUs, RSUs and tax withholding

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

Rhea-AI Filing Summary

Skyward Specialty Insurance Group, Inc. Chairman and CEO Andrew S. Robinson reported several equity compensation events involving the company’s common stock and long-term incentive plan awards. These are primarily grants, vesting, and tax withholding transactions rather than open-market purchases or sales.

On February 25, 2026, 15,151 Performance Share Units (PSUs) granted in 2023 fully vested after achieving specified performance criteria and were settled in an equal number of common shares. On the same date, Robinson received a new award of 28,841 Restricted Stock Units (RSUs), which are scheduled to vest on January 1, 2029, subject to continuous service. He was also granted 28,841 new PSUs that can vest between 0% and 200% of this amount based on performance targets through December 31, 2028. Separately, on February 26, 2026, 6,916 shares of common stock were withheld at a price of $45.89 per share to satisfy tax obligations tied to the PSU vesting, a disposition mandated by the issuer and not a discretionary sale.

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Insider Robinson Andrew S
Role Chairman & CEO, Skyward Group
Type Security Shares Price Value
Tax Withholding Common Stock 6,916 $45.89 $317K
Exercise 2023 LTIP - PSUs 15,151 $0.00 --
Grant/Award 2026 LTIP - RSUs 28,841 $0.00 --
Grant/Award 2026 LTIP - PSUs 28,841 $0.00 --
Grant/Award 2026 LTIP - PSUs 28,841 $0.00 --
Exercise Common Stock 17,575 $0.00 --
Holdings After Transaction: Common Stock — 145,574 shares (Direct); 2023 LTIP - PSUs — 0 shares (Direct); 2026 LTIP - RSUs — 28,841 shares (Direct); 2026 LTIP - PSUs — 28,841 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 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. 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 28,841 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 28,841 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 28,841 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.
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*
Robinson Andrew S

(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)
X Director 10% Owner
X Officer (give title below) Other (specify below)
Chairman & CEO, 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 17,575(1) A $0 152,490 D
Common Stock 02/26/2026 F(2) 6,916 D $45.89 145,574 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 15,151 (4) (4) Common Stock 15,151 $0 0 D
2026 LTIP - RSUs (5) 02/25/2026 A 28,841 (6) (6) Common Stock 28,841 $0 28,841 D
2026 LTIP - PSUs (7) 02/25/2026 A 28,841 (7) (7) Common Stock 28,841 $0 28,841 D
2026 LTIP - PSUs (8) 02/25/2026 A 28,841 (8) (8) Common Stock 28,841 $0 28,841 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 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.
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 28,841 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 28,841 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 28,841 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
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.
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FAQ

What insider transactions did SKWD CEO Andrew S. Robinson report on this Form 4?

Andrew S. Robinson reported vesting and settlement of 15,151 performance share units into common stock, grants of 28,841 RSUs and 28,841 PSUs, and withholding of 6,916 shares to cover tax obligations. These events reflect equity compensation activity, not open-market trading.

How many Skyward Specialty (SKWD) PSUs vested for the CEO in this filing?

A 2023 award of 15,151 performance share units fully vested on December 31, 2025 and settled after Compensation Committee certification. Each PSU converted into one share of common stock, resulting in 15,151 shares acquired in connection with this long-term performance-based award.

What new RSU award did the SKWD CEO receive and when does it vest?

On February 25, 2026, the CEO received 28,841 restricted stock units. Each RSU represents one share of common stock and, subject to continuous service, 100% of this RSU award is scheduled to vest on January 1, 2029, aligning with a multi-year retention horizon.

What are the key terms of the new PSUs granted to the SKWD CEO?

On February 25, 2026, the CEO was granted 28,841 performance share units, each equivalent to one share of common stock. The number ultimately vesting can range from 0% to 200% of this amount, based on performance condition targets through December 31, 2028.

Did the SKWD CEO sell shares on the open market in this Form 4?

The Form 4 shows 6,916 shares disposed of at $45.89 per share, but footnotes state these were shares withheld to satisfy tax obligations on PSU vesting. This withholding was mandated by the issuer and does not represent a discretionary open-market sale by the CEO.

How were the 6,916 SKWD shares disposed of in this insider filing?

The 6,916 shares were withheld by the issuer at $45.89 per share to cover tax withholding obligations tied to vested PSUs. According to the disclosure, this disposition was required by the company and is classified as a tax-withholding transaction, not a voluntary trade.