Earnings Feed
Start Free
Skyward Specialty Insurance Group, Inc.·4

Feb 27, 4:05 PM ET

Robinson Andrew S 4

4 · Skyward Specialty Insurance Group, Inc. · Filed Feb 27, 2026

Research Summary

AI-generated summary of this filing

Updated

Skyward (SKWD) CEO Andrew Robinson Exercises Awards & Sells Shares

What Happened

  • Andrew S. Robinson, Chairman & CEO of Skyward Specialty Insurance Group (SKWD), had previously awarded performance shares (PSUs) settle and received new equity awards on Feb 25, 2026. The filing shows derivative conversions/exercises resulting in 17,575 shares acquired and a 15,151-PSU award from Feb 27, 2023 that vested and was settled. On Feb 26, 2026, 6,916 shares were withheld to cover tax obligations, producing proceeds of $317,375. In addition, Robinson was granted one RSU award (28,841 RSUs) and two PSU awards (28,841 PSUs each) on Feb 25, 2026.

Key Details

  • Transaction dates: Feb 25, 2026 (exercises/awards/settlements) and Feb 26, 2026 (tax withholding sale).
  • Notable share counts and values: 17,575 shares acquired (exercise/conversion, $0 reported for derivative conversion), 15,151 PSUs settled (from a 2023 award), and 6,916 shares withheld at $45.89/share for taxes = $317,375.
  • New awards: 28,841 RSUs (vests 100% on Jan 1, 2029 if service continues) and two awards of 28,841 PSUs each (performance-based; vesting completes Dec 31, 2028; payout range can be 0%–200% depending on achievement).
  • Footnotes of interest: the 6,916-share disposition was a mandatory withholding to cover taxes (not a discretionary sale); each PSU/RSU converts to one share upon settlement; the 15,151-PSU award from Feb 27, 2023 fully vested as of Dec 31, 2025 and was settled upon committee certification.
  • Shares owned after transaction: not specified in the provided filing extract.
  • Filing timeliness: Form filed Feb 27, 2026; no late filing indication shown in the report.

Context

  • These transactions are mainly settlement of long-term compensation (PSUs/RSUs) and the issuance of new equity awards—common executive compensation events. The tax-related disposition was mandated by the company to satisfy withholding obligations and should not be read as a discretionary sale signal. The newly granted RSUs and PSUs are performance- or service-conditioned and will vest in future years if conditions are met.

Insider Transaction Report

Form 4
Period: 2026-02-25
Skyward Specialty Insurance Group, Inc.SKWD
Robinson Andrew S
DirectorChairman & CEO, Skyward Group
Transactions
  • Exercise/Conversion

    Common Stock

    [F1]
    2026-02-25+17,575→ 152,490 total
  • Tax Payment

    Common Stock

    [F2]
    2026-02-26$45.89/sh−6,916$317,375→ 145,574 total
  • Exercise/Conversion

    2023 LTIP - PSUs

    [F3][F4]
    2026-02-25−15,151→ 0 total
    → Common Stock (15,151 underlying)
  • Award

    2026 LTIP - RSUs

    [F5][F6]
    2026-02-25+28,841→ 28,841 total
    → Common Stock (28,841 underlying)
  • Award

    2026 LTIP - PSUs

    [F7]
    2026-02-25+28,841→ 28,841 total
    → Common Stock (28,841 underlying)
  • Award

    2026 LTIP - PSUs

    [F8]
    2026-02-25+28,841→ 28,841 total
    → Common Stock (28,841 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 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.
  • [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 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.
  • [F7]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.
  • [F8]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.
Signature
/s/ Stacy E. Skelton, Attorney-in-Fact|2026-02-27

Documents

1 file
  • 4
    form4-02272026_040201.xmlPrimary