Stephen Jay Sills - 19 Feb 2026 Form 4 Insider Report for Bowhead Specialty Holdings Inc. (BOW)

Role
CEO and President, Director
Signature
/s/ H. Matthew Crusey, as attorney-in-fact
Issuer symbol
BOW
Transactions as of
19 Feb 2026
Net transactions value
-$134,933
Form type
4
Filing time
23 Feb 2026, 16:14:47 UTC
Previous filing
26 Nov 2025
SEC
View on sec.gov

Reporting Owners (1)

Name Relationship Address Signature Signature date CIK
Sills Stephen Jay CEO and President, Director C/O BOWHEAD SPECIALTY HOLDINGS INC., 452 FIFTH AVENUE, NEW YORK /s/ H. Matthew Crusey, as attorney-in-fact 23 Feb 2026 0001362369

Transactions Table

Type Sym Class Transaction Value $ Shares Change % * Price $ Shares After Date Ownership Footnotes
transaction BOW Common Stock Award $0 +90,703 +12% $0.000000 876,703 19 Feb 2026 Direct F1
transaction BOW Common Stock Award $0 +88,566 +10% $0.000000 965,269 19 Feb 2026 Direct F2
transaction BOW Common Stock Tax liability $134,933 -5,419 -0.56% $24.90 959,850 20 Feb 2026 Direct F3
holding BOW Common Stock 75,000 19 Feb 2026 By Stephen J. Sills 2024 I GRAT #4
holding BOW Common Stock 97,911 19 Feb 2026 By Stephen J. Sills 2024 I GRAT #3
holding BOW Common Stock 72,000 19 Feb 2026 By Stephen J. Sills Irrevocable Family GST Exempt Trust
holding BOW Common Stock 1,141 19 Feb 2026 By Sills Family Trust 1
holding BOW Common Stock 1,141 19 Feb 2026 By Sills Family Trust 2
holding BOW Common Stock 1,141 19 Feb 2026 By Sills Family Trust 3
holding BOW Common Stock 1,141 19 Feb 2026 By Sills Family Trust 4
holding BOW Common Stock 1,141 19 Feb 2026 By Sills Family Trust 5
holding BOW Common Stock 214,469 19 Feb 2026 By Sills 2024 LLC
holding BOW Common Stock 72,500 19 Feb 2026 By Stephen J. Sills 2024 I Grant #2
* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id Content
F1 Reflects a grant of restricted stock units.
F2 Reflects a grant of performance stock units.
F3 Represents shares surrendered to the Issuer by the Reporting Person to pay required tax withholdings due upon vesting of restricted stock units.