Stephen Jay Sills
CIK: 0001362369
Transaction Breakdown
High conviction signal
Position reduction
Derivative conversions
Compensation grants
Gifts, tax withholding, conversions, dispositions to the issuer and other codes
Companies & Roles (1)
Bowhead Specialty Holdings Inc.
Discretionary Trading P&L
Holdings
Transaction History (30 total)
- May 22, 2026BOW
Bowhead Specialty Holdings Inc.
Tax Payment(F)Direct13.1K shares at avg. $28.46$371K - May 22, 2026BOW
Bowhead Specialty Holdings Inc.
Tax Payment(F)Direct24.4K shares at avg. $28.46$693K - Mar 13, 2026BOW
Bowhead Specialty Holdings Inc.
Gift(G)Direct120K shares- - Mar 13, 2026BOW
Bowhead Specialty Holdings Inc.
Gift(G)Indirect120K shares- - Mar 12, 2026BOW
Bowhead Specialty Holdings Inc.
Gift(G)Indirect1.5K shares- - Mar 12, 2026BOW
Bowhead Specialty Holdings Inc.
Gift(G)Indirect1.5K shares- - Mar 12, 2026BOW
Bowhead Specialty Holdings Inc.
Gift(G)Indirect1.5K shares- - Mar 12, 2026BOW
Bowhead Specialty Holdings Inc.
Gift(G)Indirect1.5K shares- - Mar 12, 2026BOW
Bowhead Specialty Holdings Inc.
Gift(G)Direct7.7K shares- - Mar 12, 2026BOW
Bowhead Specialty Holdings Inc.
Gift(G)Indirect1.5K shares- - Feb 20, 2026BOW
Bowhead Specialty Holdings Inc.
Tax Payment(F)Direct5.4K shares at avg. $24.90$135K - Feb 19, 2026BOW
Bowhead Specialty Holdings Inc.
Award(A)Direct90.7K shares- - Feb 19, 2026BOW
Bowhead Specialty Holdings Inc.
Award(A)Direct88.6K shares- - Nov 26, 2025BOW
Bowhead Specialty Holdings Inc.
Gift(G)Direct75K shares- - Nov 26, 2025BOW
Bowhead Specialty Holdings Inc.
Gift(G)Indirect75K shares- - Aug 26, 2025BOW
Bowhead Specialty Holdings Inc.
Gift(G)Direct163.2K shares- - Aug 26, 2025BOW
Bowhead Specialty Holdings Inc.
Gift(G)Indirect65.3K shares- - Aug 26, 2025BOW
Bowhead Specialty Holdings Inc.
Gift(G)Indirect97.9K shares- - Jul 15, 2025BOW
Bowhead Specialty Holdings Inc.
Gift(G)Indirect1.1K shares- - Jul 15, 2025BOW
Bowhead Specialty Holdings Inc.
Gift(G)Indirect1.1K shares- - Jul 15, 2025BOW
Bowhead Specialty Holdings Inc.
Gift(G)Indirect1.1K shares- - Jul 15, 2025BOW
Bowhead Specialty Holdings Inc.
Gift(G)Direct12.4K shares- - Jul 15, 2025BOW
Bowhead Specialty Holdings Inc.
Gift(G)Indirect1.1K shares- - Jul 15, 2025BOW
Bowhead Specialty Holdings Inc.
Gift(G)Indirect6.7K shares- - Jul 15, 2025BOW
Bowhead Specialty Holdings Inc.
Gift(G)Indirect1.1K shares-
| Type | Shares | Price | Ownership | |||
|---|---|---|---|---|---|---|
| May 22, 2026 | BOW Bowhead Specialty Holdings Inc. | Tax Payment(F) | 13,053 | $28.46 | $371,488 | Direct |
| May 22, 2026 | BOW Bowhead Specialty Holdings Inc. | Tax Payment(F) | 24,353 | $28.46 | $693,086 | Direct |
| Mar 13, 2026 | BOW Bowhead Specialty Holdings Inc. | Gift(G) | 120,000 | - | $0 | Direct |
| Mar 13, 2026 | BOW Bowhead Specialty Holdings Inc. | Gift(G) | 120,000 | - | $0 | Indirect |
| Mar 12, 2026 | BOW Bowhead Specialty Holdings Inc. | Gift(G) | 1,540 | - | $0 | Indirect |
| Mar 12, 2026 | BOW Bowhead Specialty Holdings Inc. | Gift(G) | 1,540 | - | $0 | Indirect |
| Mar 12, 2026 | BOW Bowhead Specialty Holdings Inc. | Gift(G) | 1,540 | - | $0 | Indirect |
| Mar 12, 2026 | BOW Bowhead Specialty Holdings Inc. | Gift(G) | 1,540 | - | $0 | Indirect |
| Mar 12, 2026 | BOW Bowhead Specialty Holdings Inc. | Gift(G) | 7,700 | - | $0 | Direct |
| Mar 12, 2026 | BOW Bowhead Specialty Holdings Inc. | Gift(G) | 1,540 | - | $0 | Indirect |
| Feb 20, 2026 | BOW Bowhead Specialty Holdings Inc. | Tax Payment(F) | 5,419 | $24.90 | $134,933 | Direct |
| Feb 19, 2026 | BOW Bowhead Specialty Holdings Inc. | Award(A) | 90,703 | - | $0 | Direct |
| Feb 19, 2026 | BOW Bowhead Specialty Holdings Inc. | Award(A) | 88,566 | - | $0 | Direct |
| Nov 26, 2025 | BOW Bowhead Specialty Holdings Inc. | Gift(G) | 75,000 | - | - | Direct |
| Nov 26, 2025 | BOW Bowhead Specialty Holdings Inc. | Gift(G) | 75,000 | - | - | Indirect |
| Aug 26, 2025 | BOW Bowhead Specialty Holdings Inc. | Gift(G) | 163,185 | - | - | Direct |
| Aug 26, 2025 | BOW Bowhead Specialty Holdings Inc. | Gift(G) | 65,274 | - | - | Indirect |
| Aug 26, 2025 | BOW Bowhead Specialty Holdings Inc. | Gift(G) | 97,911 | - | - | Indirect |
| Jul 15, 2025 | BOW Bowhead Specialty Holdings Inc. | Gift(G) | 1,141 | - | - | Indirect |
| Jul 15, 2025 | BOW Bowhead Specialty Holdings Inc. | Gift(G) | 1,141 | - | - | Indirect |
| Jul 15, 2025 | BOW Bowhead Specialty Holdings Inc. | Gift(G) | 1,141 | - | - | Indirect |
| Jul 15, 2025 | BOW Bowhead Specialty Holdings Inc. | Gift(G) | 12,431 | - | - | Direct |
| Jul 15, 2025 | BOW Bowhead Specialty Holdings Inc. | Gift(G) | 1,141 | - | - | Indirect |
| Jul 15, 2025 | BOW Bowhead Specialty Holdings Inc. | Gift(G) | 6,726 | - | - | Indirect |
| Jul 15, 2025 | BOW Bowhead Specialty Holdings Inc. | Gift(G) | 1,141 | - | - | Indirect |
1-25 of 30 transactions
About Sills Stephen Jay
Sills Stephen Jay (SEC CIK 0001362369) files insider reports with the SEC as CEO and President of Bowhead Specialty Holdings Inc. (BOW).
Signal8 holds 12 ownership filings by Sills Stephen Jay (1 Form 3, 11 Form 4), filed between Feb 25, 2025 and May 27, 2026. Those filings report 30 transactions, from Feb 21, 2025 to May 22, 2026. Signal8's Form 4 history starts in Sep 2024.
The business address on Sills Stephen Jay's filings is in NEW YORK, NY.
Recent filings by Sills Stephen Jay
- May 22, 2026: Tax withholdings of BOW shares (2 lines, Form 4, code F).
- Mar 13, 2026: Gifts of BOW shares (2 lines, Form 4, code G).
- Mar 12, 2026: Gifts of BOW shares (6 lines, Form 4, code G).
- Feb 20, 2026: Tax withholding of BOW shares (Form 4, code F).
- Feb 19, 2026: Grants or awards of BOW shares (2 lines, Form 4, code A).
Other insiders filing for Bowhead Specialty Holdings Inc. (BOW)
- Walker Derek Z, Director
- Newman David John, Chief Underwriting Officer
- Mulcahey Brad, CFO and Treasurer
- Yap Shirley Shek Li, Chief Accounting Officer
- Baker Tom, Director
- Brock-Kyle Angela, Director