Kapadia Sandip A 4
4 · Skyward Specialty Insurance Group, Inc. · Filed Feb 27, 2026
Research Summary
AI-generated summary of this filing
Skyward (SKWD) Head of Actuarial Sandip Kapadia Exercises, Receives Awards
What Happened
- Sandip Kapadia, Head of Actuarial at Skyward Specialty Insurance Group (SKWD), had performance shares/derivatives settle into common stock and had shares withheld to cover taxes, and on Feb 25, 2026 received new equity awards.
- Reported activity includes a gross conversion/settlement of vested PSUs/derivatives (2,343 shares reported as acquired on Feb 25, 2026 and a related conversion of 2,020 PSUs), a tax-withholding disposition of 847 shares on Feb 26, 2026 (847 x $45.89 = $38,869), and three awards granted on Feb 25, 2026 totaling 10,094 units (2,884 RSUs, 2,884 PSUs, 4,326 RSUs). These awards are not purchases of stock but compensation grants/derivative settlements.
Key Details
- Transaction dates: conversions/awards dated Feb 25, 2026; tax-withholding disposition dated Feb 26, 2026; Form 4 filed Feb 27, 2026 (appears timely).
- Tax withholding: 847 shares were withheld to cover tax obligations at $45.89/share for ~$38,869 (disposition code F). The filing notes this withholding was mandated by the issuer and not a discretionary sale.
- New awards (granted Feb 25, 2026): 2,884 RSUs (100% vest 1/1/2029), 2,884 PSUs (0–200% payout based on performance; vests 12/31/2028), 4,326 RSUs (50% vests 1/1/2029, 50% vests 1/1/2030).
- Vested award settled: 2,020 PSUs were from a 2023 award that fully vested Dec 31, 2025 and were settled upon Compensation Committee certification (each PSU = one share).
- Transaction codes: M = exercise/conversion of derivative, A = award/grant, F = payment of exercise price or tax withholding. The F disposition reflects mandated withholding, not an open-market sale.
- Shares owned after the transactions are not reported in the excerpt provided.
Context
- These transactions are largely compensation-related (vesting and grants), not open-market purchases or voluntary sales that typically signal a trading view. The tax-withholding disposition is a routine, issuer-mandated withholding to satisfy tax obligations after PSU settlement (effectively a cashless settlement element).
- PSUs and RSUs represent rights to future shares; PSUs may pay out more or fewer shares depending on performance targets. These awards vest over multi-year schedules, so they reflect long-term compensation rather than immediate trading.
Insider Transaction Report
Form 4
Kapadia Sandip A
Head of Actuarial
Transactions
- Exercise/Conversion
Common Stock
[F1]2026-02-25+2,343→ 17,888 total - Tax Payment
Common Stock
[F2]2026-02-26$45.89/sh−847$38,869→ 17,041 total - Exercise/Conversion
2023 LTIP - PSUs
[F3][F4]2026-02-25−2,020→ 0 total→ Common Stock (2,020 underlying) - Award
2026 LTIP - RSUs
[F5][F6]2026-02-25+2,884→ 2,884 total→ Common Stock (2,884 underlying) - Award
2026 LTIP - PSUs
[F7]2026-02-25+2,884→ 2,884 total→ Common Stock (2,884 underlying) - Award
2026 Bright Future - RSUs
[F5][F8]2026-02-25+4,326→ 4,326 total→ Common Stock (4,326 underlying)
Footnotes (8)
- [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.
- [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.
- [F3]Each PSU represents the right to receive one share of the Issuer's Common Stock upon settlement.
- [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.
- [F5]Each Restricted Stock Unit ("RSU") represents the right to receive one share of the Issuer's Common Stock upon settlement.
- [F6]On February 25, 2026, the Reporting Person was granted an RSU Award in the amount of 2,884 RSUs. Subject to the Reporting Person's continuous service through the vesting date, 100% of the RSUs shall vest on January 1, 2029.
- [F7]On February 25, 2026, the Reporting Person was granted 2,884 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.
- [F8]On February 25, 2026, the Reporting Person was granted an RSU Award in the amount of 4,326 RSUs. Subject to the terms of the RSU Agreement and the Reporting Person's continuous service through the vesting dates, 50% of the RSUs shall vest on January 1, 2029 and the remaining 50% of the RSUs will vest on January 1, 2030.
Signature
/s/ Stacy E. Skelton, Attorney-in-Fact|2026-02-27