Insider · CIK 0001362369

Sills Stephen Jay

Reports to the SEC for 2 companies · NEW YORK, NY

sec.gov

Transactions

Companies

Filings

CIK

0001362369

Forms 4 and 5

Insider transactions

43 trades

Date	Company	Role	Code	Shares	Price	Value	Shares after
2026-05-22	BOWBowhead Specialty Holdings Inc.F Tax Payment	Director, CEO and President	FTax Payment	−24.4K sh	$28.46	−$693K	838,926
2026-05-22	BOWBowhead Specialty Holdings Inc.F Tax Payment	Director, CEO and President	FTax Payment	−13.1K sh	$28.46	−$371K	850,226
2026-03-13	BOWBowhead Specialty Holdings Inc.G Gift	Director, CEO and President	GGift	−120K sh	—	—	832,150
2026-03-13	BOWBowhead Specialty Holdings Inc.G Gift	Director, CEO and President	GGift	+120K sh	—	—	120,000
2026-03-12	BOWBowhead Specialty Holdings Inc.G Gift	Director, CEO and President	GGift	+1,540 sh	—	—	2,681
2026-03-12	BOWBowhead Specialty Holdings Inc.G Gift	Director, CEO and President	GGift	+1,540 sh	—	—	2,681
2026-03-12	BOWBowhead Specialty Holdings Inc.G Gift	Director, CEO and President	GGift	+1,540 sh	—	—	2,681
2026-03-12	BOWBowhead Specialty Holdings Inc.G Gift	Director, CEO and President	GGift	+1,540 sh	—	—	2,681
2026-03-12	BOWBowhead Specialty Holdings Inc.G Gift	Director, CEO and President	GGift	−7,700 sh	—	—	952,150
2026-03-12	BOWBowhead Specialty Holdings Inc.G Gift	Director, CEO and President	GGift	+1,540 sh	—	—	2,681
2026-02-20	BOWBowhead Specialty Holdings Inc.F Tax Payment	Director, CEO and President	FTax Payment	−5,419 sh	$24.90	−$135K	959,850
2026-02-19	BOWBowhead Specialty Holdings Inc.A Award	Director, CEO and President	AAward	+90.7K sh	—	—	876,703
2026-02-19	BOWBowhead Specialty Holdings Inc.A Award	Director, CEO and President	AAward	+88.6K sh	—	—	965,269
2025-11-26	BOWBowhead Specialty Holdings Inc.G Gift	Director, CEO and President	GGift	−75K sh	—	—	786,000
2025-11-26	BOWBowhead Specialty Holdings Inc.G Gift	Director, CEO and President	GGift	+75K sh	—	—	75,000
2025-08-26	BOWBowhead Specialty Holdings Inc.G Gift	Director, CEO and President	GGift	−163K sh	—	—	861,000
2025-08-26	BOWBowhead Specialty Holdings Inc.G Gift	Director, CEO and President	GGift	−163K sh	—	—	861,000
2025-08-26	BOWBowhead Specialty Holdings Inc.G Gift	Director, CEO and President	GGift	+97.9K sh	—	—	97,911
2025-08-26	BOWBowhead Specialty Holdings Inc.G Gift	Director, CEO and President	GGift	+65.3K sh	—	—	72,000
2025-08-26	BOWBowhead Specialty Holdings Inc.G Gift	Director, CEO and President	GGift	+65.3K sh	—	—	65,274
2025-08-26	BOWBowhead Specialty Holdings Inc.G Gift	Director, CEO and President	GGift	+97.9K sh	—	—	97,911
2025-07-15	BOWBowhead Specialty Holdings Inc.G Gift	Director, CEO and President	GGift	+6,726 sh	—	—	6,726
2025-07-15	BOWBowhead Specialty Holdings Inc.G Gift	Director, CEO and President	GGift	−12.4K sh	—	—	1,024,185
2025-07-15	BOWBowhead Specialty Holdings Inc.G Gift	Director, CEO and President	GGift	+1,141 sh	—	—	1,141
2025-07-15	BOWBowhead Specialty Holdings Inc.G Gift	Director, CEO and President	GGift	+1,141 sh	—	—	1,141
2025-07-15	BOWBowhead Specialty Holdings Inc.G Gift	Director, CEO and President	GGift	+1,141 sh	—	—	1,141
2025-07-15	BOWBowhead Specialty Holdings Inc.G Gift	Director, CEO and President	GGift	+1,141 sh	—	—	1,141
2025-07-15	BOWBowhead Specialty Holdings Inc.G Gift	Director, CEO and President	GGift	+1,141 sh	—	—	1,141
2025-05-22	BOWBowhead Specialty Holdings Inc.F Tax Payment	Director, CEO and President	FTax Payment	−11.9K sh	$38.08	−$454K	1,036,616
2025-05-12	BOWBowhead Specialty Holdings Inc.G Gift	Director, CEO and President	GGift	+72.5K sh	—	—	72,500
2025-05-12	BOWBowhead Specialty Holdings Inc.G Gift	Director, CEO and President	GGift	−72.5K sh	—	—	1,048,537
2025-02-21	BOWBowhead Specialty Holdings Inc.A Award	Director, CEO and President	AAward	+67.5K sh	—	—	1,121,037
2025-02-21	BOWBowhead Specialty Holdings Inc.A Award	Director, CEO and President	AAward	+65.6K sh	—	—	1,053,511
2024-05-28	BOWBowhead Specialty Holdings Inc.P Purchase	Director, CEO and President	PPurchase	+58.8K sh	$17.00	+$1M	180,588
2008-06-19	Darwin Professional Underwriters IncG Gift	Director, President and CEO	GGift	−19.8K sh	—	—	420,000
2008-06-19	Darwin Professional Underwriters IncJ Other	Director, President and CEO	JOther	+6,606 sh	—	—	7,506
2008-06-06	Darwin Professional Underwriters IncJ Other	Director, President and CEO	JOther	−900 sh	—	—	0
2008-06-06	Darwin Professional Underwriters IncJ Other	Director, President and CEO	JOther	−1,050 sh	—	—	0
2008-06-06	Darwin Professional Underwriters IncJ Other	Director, President and CEO	JOther	−1,000 sh	—	—	0
2008-06-06	Darwin Professional Underwriters IncJ Other	Director, President and CEO	JOther	−21.4K sh	—	—	439,819
2008-06-06	Darwin Professional Underwriters IncJ Other	Director, President and CEO	JOther	+21.4K sh	—	—	295,404
2007-06-06	Darwin Professional Underwriters IncJ Other	Director, President and CEO	JOther	+21.2K sh	—	—	687,078
2007-06-06	Darwin Professional Underwriters IncJ Other	Director, President and CEO	JOther	−21.2K sh	—	—	41,325

Recent filings

Accepted (ET)
May 274/A
Sills Stephen Jay0001362369-26-000006
SEC(opens sec.gov)
May 264
Sills Stephen Jay0001362369-26-000004
SEC(opens sec.gov)
Mar 134
Sills Stephen Jay0001628280-26-017724
SEC(opens sec.gov)
Feb 234
Sills Stephen Jay0001362369-26-000002
SEC(opens sec.gov)
Nov 264
Sills Stephen Jay0001362369-25-000004
SEC(opens sec.gov)
Sep 34/A
Sills Stephen Jay0002002473-25-000071
SEC(opens sec.gov)
Sep 24
Sills Stephen Jay0002002473-25-000068
SEC(opens sec.gov)

Companies

Address

C/O BOWHEAD SPECIALTY HOLDINGS INC. 452 FIFTH AVENUE

NEW YORK, NY, 10018