STOCK TITAN
  1. Home
  2. Sec-filings
  3. SKWD
  4. [Form 4] Skyward Specialty Insurance Group, Inc. Insider Trading Activity

Skyward Specialty (SKWD) executive settles PSUs and has shares withheld for tax

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

Rhea-AI Filing Summary

Skyward Specialty Insurance Group, Inc. Head of Actuarial Sandip A. Kapadia reported compensation-related share activity tied to performance awards. On May 6, 2026, he acquired 2,686 shares of common stock, including shares delivered upon settlement of previously granted Performance Share Units (PSUs).

In a separate line item the same day, 1,374 shares of common stock were disposed of at $43.68 per share to satisfy tax withholding obligations mandated by the company. After these transactions, Kapadia directly owned 19,727 shares of common stock. Footnotes explain that each PSU represented the right to receive one share and that the 2,020 PSUs awarded on February 27, 2023, fully vested based on performance criteria through December 31, 2025 and were settled after certification by the Compensation Committee.

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 --
Exercise Common Stock 2,686 $0.00 --
Tax Withholding Common Stock 1,374 $43.68 $60K
Holdings After Transaction: 2023 LTIP - PSUs — 0 shares (Direct, null); Common Stock — 19,727 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 2,020 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.
Shares acquired 2,686 shares Common stock acquired on May 6, 2026
Tax withholding shares 1,374 shares Shares withheld to cover tax obligations on May 6, 2026
Tax withholding price $43.68 per share Price used for tax-withholding disposition
Post-transaction holdings 19,727 shares Common stock directly owned after transactions
PSUs awarded 2,020 PSUs Award granted on February 27, 2023
PSU performance period January 1, 2023–December 31, 2025 Period over which PSU performance criteria applied
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"
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
"The PSUs are subject to obtaining specified performance criteria from January 1, 2023 through December 31, 2025."
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
"represents 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 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.
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*
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)

Source: View Original Filing on SEC EDGAR

FAQ

What insider transactions did SKWD executive Sandip Kapadia report?

Sandip Kapadia reported compensation-related share activity on May 6, 2026. He acquired 2,686 shares of common stock from PSU settlement and had 1,374 shares withheld to cover tax obligations, leaving him with 19,727 shares directly owned.

Were Sandip Kapadia’s SKWD share dispositions open-market sales?

No, the 1,374-share disposition was for tax withholding obligations. Footnotes state the shares were withheld by the issuer in connection with PSU vesting and settlement and that this disposition was mandated by the company, not a discretionary market sale.

How many Skyward Specialty shares does Sandip Kapadia hold after these transactions?

Following the reported transactions, Sandip Kapadia directly owns 19,727 shares of Skyward Specialty common stock. This total reflects both the PSU-related share acquisition and the tax-withholding share disposition recorded on May 6, 2026.

What Performance Share Units (PSUs) were involved in the SKWD Form 4 filing?

The filing references 2,020 PSUs awarded on February 27, 2023. Footnotes state these PSUs were subject to performance criteria from January 1, 2023 through December 31, 2025, fully vested at the end of that period, and then settled into common shares.

How do the SKWD PSUs convert into common stock for Sandip Kapadia?

Each PSU represents the right to receive one share of Skyward Specialty common stock upon settlement. Once performance criteria are certified by the Compensation Committee, vested PSUs are settled and the corresponding shares are delivered to the reporting person.

Is Sandip Kapadia’s SKWD Form 4 transaction a routine compensation event?

Yes, the activity reflects PSU vesting and settlement plus tax withholding. Footnotes describe the disposition as issuer-mandated for tax obligations, indicating a routine compensation-driven event rather than an elective purchase or sale in the open market.