Bowhead Specialty Holdings INC Form 4 insider transactions

Stephen Jay Sills, CEO and President of Bowhead Specialty Holdings Inc., reported a transaction involving the surrender of shares for tax withholdings and a transfer of shares between trusts.

David John Newman, Chief Underwriting Officer of Bowhead Specialty Holdings Inc., reported a transaction involving the surrender of shares to cover tax withholdings.

Shirley Shek Li Yap, Chief Accounting Officer of Bowhead Specialty Holdings Inc., reported a transaction involving the surrender of shares for tax withholdings.

Bowhead Specialty Holdings Inc. CFO and Treasurer Brad Mulcahey reported a transaction involving the sale of 3,506 shares of common stock.

Stephen Jay Sills, CEO and President of Bowhead Specialty Holdings Inc., reported a transaction involving the surrender of shares for tax withholdings and a transfer of shares between entities.

Tom Baker, a Director at Bowhead Specialty Holdings Inc., acquired 3,361 shares of common stock on April 30, 2026.

Bowhead Specialty Holdings Inc. Director Angela Brock-Kyle acquired 6,722 shares of common stock on April 30, 2026.

David Thomas Foy, a Director at Bowhead Specialty Holdings Inc., reported the acquisition of 3,361 shares of common stock on April 30, 2026.

Fabian Fondriest, a Director at Bowhead Specialty Holdings Inc., reported the acquisition of 6,722 shares of common stock on April 30, 2026.

David Clifford Holman, a Director at Bowhead Specialty Holdings Inc., reported a transaction involving 3,361 restricted stock units acquired on April 30, 2026.

Bowhead Specialty Holdings Inc. director, Lowenstein Price, acquired 3,361 shares of common stock on April 30, 2026, as reported in a Form 4 filing.

Director Ava Schnidman reported transactions involving restricted stock units and common stock.

Bowhead Specialty Holdings CEO Stephen Jay Sills reported gifting a significant number of common shares to family trusts and GRATs for estate planning purposes.

Bowhead Specialty Holdings Inc.'s CFO and Treasurer, Brad Mulcahey, was granted 25,145 restricted stock units and subsequently disposed of 1,274 shares to cover tax withholdings.

Bowhead Specialty Holdings Inc.'s Chief Underwriting Officer, David John Newman, received a grant of 23,488 restricted stock units and subsequently surrendered 1,443 shares for tax obligations.

Bowhead Specialty Holdings Inc. CEO Stephen Jay Sills reported the acquisition of restricted and performance stock units and a disposition for tax withholding.

Bowhead Specialty Holdings Inc.'s Chief Accounting Officer, Shirley Shek Li Yap, reported the acquisition of restricted stock units and a subsequent sale of shares to cover tax obligations.

Bowhead Specialty Holdings Inc. Director Angela Brock-Kyle reports an acquisition of 4,038 common shares, increasing her direct beneficial ownership to 36,773 shares.

Bowhead Specialty Holdings Inc. CEO and President Stephen Jay Sills transferred 75,000 shares of common stock to a grantor trust.

Bowhead Specialty Holdings Inc. CEO Stephen Jay Sills filed an amended Form 4 detailing transfers of common stock to family trusts.

Bowhead Specialty Holdings CEO Stephen Jay Sills transferred 163,185 shares of common stock into two grantor trusts for estate planning purposes.

Bowhead Specialty Holdings Director and 10% owner Matthew Botein sold 2,000,000 shares of common stock at $30.66 per share as part of an underwritten public offering.

Gallatin Point Capital LLC and affiliated entities sold 2 million shares of Bowhead Specialty Holdings Inc. common stock at $30.66 per share.

Bowhead Specialty Holdings Inc. Director David Clifford Holman was granted 2,355 restricted stock units of common stock on July 30, 2025.

Stephen Jay Sills, CEO and President of Bowhead Specialty Holdings Inc., transferred 12,431 shares of common stock to six family trusts as gifts.

Brad Mulcahey, CFO and Treasurer of Bowhead Specialty Holdings Inc., disposed of 1,027 shares of common stock to cover tax obligations related to the vesting of restricted stock units.

David John Newman, Chief Underwriting Officer of Bowhead Specialty Holdings Inc., disposed of 2,118 shares of common stock to cover tax withholdings related to restricted stock unit vesting.

Bowhead Specialty Holdings Inc.'s Chief Accounting Officer, Shirley Shek Li Yap, reported a disposition of 680 common shares valued at $37.17 per share to cover tax obligations related to restricted stock unit vesting.

Stephen Jay Sills, CEO and President of Bowhead Specialty Holdings Inc., disposed of 11,921 shares of common stock valued at $38.08 per share to cover tax withholdings related to restricted stock unit vesting.

Stephen Jay Sills, CEO and President of Bowhead Specialty Holdings, reports a transfer of 72,500 common stock shares to a grantor trust.