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Skyward Specialty Insurance Group, Inc. (NASDAQ: SKWD) PSU vesting

(Neutral)
(Neutral)
Form Type
4

Rhea-AI Filing Summary

Skyward Specialty Insurance Group, Inc. reports that Head of Actuarial Sandip A. Kapadia settled a 2023 LTIP Performance Share Unit award on May 6, 2026. He exercised 2,020 PSUs granted on February 27, 2023, receiving 2,686 shares of Common Stock after the award fully vested based on performance through December 31, 2025.

In connection with this vesting, 1,374 shares were automatically withheld at $43.6800 per share to satisfy tax withholding obligations, a disposition mandated by the issuer and not discretionary. After these transactions, he directly owns 18,353 shares of Skyward Specialty common stock.

Positive

  • None.

Negative

  • None.
Insider Kapadia Sandip A
Role Head of Actuarial
Type Security Shares Price Value
Exercise 2023 LTIP - PSUs 2,020 $0.00 $0.00
Exercise Common Stock 2,686 $0.00 $0.00
Exercise Price or Tax Liability Common Stock 1,374 $43.68 $60K
Holdings After Transaction: 2023 LTIP - PSUs — 0 shares (Direct); Common Stock — 18,353 shares (Direct)
Footnotes (4)
  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 2,020 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 exercised 2,020 PSUs 2023 LTIP Performance Share Units exercised into Common Stock on May 6, 2026
Common shares acquired 2,686 shares Common Stock received upon settlement of PSUs on May 6, 2026
Shares withheld for taxes 1,374 shares Shares withheld to cover tax withholding obligations upon PSU vesting
Tax withholding price $43.6800 per share Per-share value used for the tax-withholding share disposition
Post-transaction holdings 18,353 shares Common Stock directly owned by Kapadia after reported transactions
Original PSU award size 2,020 PSUs Performance Share Units awarded on February 27, 2023 under the 2023 LTIP
Performance Share Units ("PSUs") financial
"settlement of the Performance Share Units ("PSUs") listed"
tax withholding obligations financial
"shares withheld to cover tax withholding obligations in connection"
vesting and settlement financial
"in connection with the vesting and settlement of the PSUs"
Compensation Committee regulatory
"settled upon certification by the Compensation Committee of the Board"
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.
LTIP financial
"2023 LTIP - PSUs"
LTIP stands for Long-Term Incentive Plan, a company program that pays executives and key employees with stock, cash, or other rewards tied to multi-year performance targets and continued service. It matters to investors because it aligns management’s pay with the company’s long-term success—like paying a gardener in future harvest to ensure the orchard thrives—while also affecting share count and reported expenses, which can influence future returns.

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

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FAQ

What insider transactions did SKWD report for Sandip A. Kapadia?

Skyward Specialty reported that Sandip A. Kapadia settled a 2023 Performance Share Unit award, exercising 2,020 PSUs into 2,686 shares of Common Stock, with a portion of those shares withheld to cover tax obligations mandated by the company.

How many Skyward Specialty (SKWD) shares did Kapadia acquire from the PSU settlement?

Kapadia received 2,686 shares of Common Stock through settlement of his 2023 LTIP PSUs. These PSUs were granted on February 27, 2023 and fully vested based on performance measured from January 1, 2023 through December 31, 2025.

How many SKWD shares were withheld for taxes and at what price?

In connection with the PSU vesting, 1,374 shares of Skyward Specialty Common Stock were withheld to satisfy tax withholding obligations at a price of $43.6800 per share, a disposition described as mandated by the issuer rather than a discretionary sale.

What are Sandip A. Kapadia’s post-transaction SKWD holdings?

After the reported PSU exercise and tax withholding, Sandip A. Kapadia directly owns 18,353 shares of Skyward Specialty Insurance Group, Inc. Common Stock, reflecting his current reported equity position following these May 6, 2026 transactions.

What were the key terms of Kapadia’s 2023 PSUs at Skyward Specialty (SKWD)?

Kapadia was awarded 2,020 Performance Share Units on February 27, 2023 under the 2023 LTIP. The PSUs were tied to performance criteria for January 1, 2023 through December 31, 2025, could vest between 0% and 150% of target, and fully vested by year-end 2025.
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*
Kapadia Sandip A

(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)
Head of Actuarial
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 Stock05/06/2026M2,686(1)A$019,727D
Common Stock05/06/2026F(2)1,374D$43.6818,353D
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)05/06/2026M2,020 (4) (4)Common Stock2,020$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 2,020 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)