As of September 29, 2026, Bowhead Specialty Holdings's top three insider holders are Matthew Botein (Director, 8.97Mn shares), Point Capital Llc Gallatin (Director, 8.97Mn shares), Family Mutual Insurance Company, S.I. American (Director, 6.06Mn shares).
| # | Insider | Position | Direct | Indirect | Total | Share of Insiders | Last Filed |
|---|---|---|---|---|---|---|---|
| 1 | Matthew Botein | Director, TenPercentOwner | 0 | 8,968,445 | 8,968,445 | 37.1% | 08 Aug, 2025 |
| 2 | Point Capital Llc Gallatin | Director, TenPercentOwner | 0 | 8,968,445 | 8,968,445 | 37.1% | 08 Aug, 2025 |
| 3 | Family Mutual Insurance Company, S.I. American | Director, TenPercentOwner, Other | 4,700,761 | 0 | 4,700,761 | 19.4% | 28 Oct, 2024 |
| 4 | Stephen Jay Sills | Ceo And President | 850,226 | 0 | 850,226 | 3.5% | 27 May, 2026 |
| 5 | David John Newman | Chief Underwriting Officer | 295,077 | 0 | 295,077 | 1.2% | 27 May, 2026 |
| 6 | Brad Mulcahey | Cfo And Treasurer | 135,300 | 0 | 135,300 | 0.6% | 27 May, 2026 |
| 7 | Shirley Shek Li Yap | Chief Accounting Officer | 82,879 | 0 | 82,879 | 0.3% | 27 May, 2026 |
| 8 | Insurance Holdings Lp Bowhead | Director, TenPercentOwner | 59,053 | 0 | 59,053 | 0.2% | 20 Sep, 2024 |
| 9 | Fabian Fondriest | Director | 49,818 | 0 | 49,818 | 0.2% | 04 May, 2026 |
| 10 | Angela Brock-Kyle | Director | 43,495 | 0 | 43,495 | 0.2% | 04 May, 2026 |
| 11 | Tom Baker | Director | 10,085 | 0 | 10,085 | 0.0% | 04 May, 2026 |
| 12 | David Thomas Foy | Director | 10,085 | 0 | 10,085 | 0.0% | 04 May, 2026 |
| 13 | David Clifford Holman | Director | 5,716 | 0 | 5,716 | 0.0% | 04 May, 2026 |
| 14 | Ava Schnidman | Director | 5,380 | 0 | 5,380 | 0.0% | 04 May, 2026 |
| 15 | Price Lowenstein | Director | 3,361 | 0 | 3,361 | 0.0% | 04 May, 2026 |
Each row is that insider’s most recently reported position, from Form 4 filings over the last 60 months — which is why this total does not tie to the quarterly series above, where a quarter counts only the insiders who filed in it. Shares held through a fund or institutional portfolio are counted on the institutional ownership page instead.
| Date | Insider | Position | Transaction | Shares | Price | Value | Shares Held After | Ownership |
|---|---|---|---|---|---|---|---|---|
| 22 May, 2026 | Stephen Jay Sills | Ceo And President | Disposed F | 13,053 | $28.46 | $371.49K | 850,226 | Direct |
| 23 May, 2026 | Shirley Shek Li Yap | Chief Accounting Officer | Disposed F | 679 | $23.80 | $16.16K | 82,879 | Direct |
| 23 May, 2026 | David John Newman | Chief Underwriting Officer | Disposed F | 2,118 | $28.30 | $59.94K | 295,077 | Direct |
| 23 May, 2026 | Shirley Shek Li Yap | Chief Accounting Officer | Disposed F | 2,353 | $28.30 | $66.59K | 81,205 | Direct |
| 23 May, 2026 | Brad Mulcahey | Cfo And Treasurer | Disposed F | 1,027 | $28.30 | $29.06K | 135,300 | Direct |
| 22 May, 2026 | Stephen Jay Sills | Ceo And President | Disposed F | 24,353 | $28.46 | $693.09K | 838,926 | Direct |
| 23 May, 2026 | Brad Mulcahey | Cfo And Treasurer | Disposed F | 3,506 | $28.30 | $99.22K | 132,821 | Direct |
| 23 May, 2026 | David John Newman | Chief Underwriting Officer | Disposed F | 4,506 | $28.30 | $127.52K | 292,689 | Direct |
| 30 Apr, 2026 | David Clifford Holman | Director | Acquired A | 3,361 | $0.00 | $0 | 5,716 | Direct |
| 30 Apr, 2026 | Angela Brock-Kyle | Director | Acquired A | 6,722 | $0.00 | $0 | 43,495 | Direct |
| 30 Apr, 2026 | Price Lowenstein | Director | Acquired A | 3,361 | $0.00 | $0 | 3,361 | Direct |
| 30 Apr, 2026 | Fabian Fondriest | Director | Acquired A | 6,722 | $0.00 | $0 | 49,818 | Direct |
| 30 Apr, 2026 | David Thomas Foy | Director | Acquired A | 3,361 | $0.00 | $0 | 10,085 | Direct |
| 30 Apr, 2026 | Ava Schnidman | Director | Acquired A | 3,361 | $0.00 | $0 | 5,380 | Direct |
| 30 Apr, 2026 | Tom Baker | Director | Acquired A | 3,361 | $0.00 | $0 | 10,085 | Direct |
| 12 Mar, 2026 | Stephen Jay Sills | Ceo And President | Disposed G | 7,700 | $0.00 | $0 | 952,150 | Direct |
| 12 Mar, 2026 | Stephen Jay Sills | Ceo And President | Acquired G | 1,540 | $0.00 | $0 | 2,681 | Indirect |
| 12 Mar, 2026 | Stephen Jay Sills | Ceo And President | Acquired G | 1,540 | $0.00 | $0 | 2,681 | Indirect |
| 12 Mar, 2026 | Stephen Jay Sills | Ceo And President | Acquired G | 1,540 | $0.00 | $0 | 2,681 | Indirect |
| 12 Mar, 2026 | Stephen Jay Sills | Ceo And President | Acquired G | 1,540 | $0.00 | $0 | 2,681 | Indirect |