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Skyward Specialty Insurance Group, Inc.·4

Feb 27, 4:05 PM ET

Robinson Andrew S 4

Research Summary

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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.