As of September 29, 2026, Skyward Specialty Insurance's top three insider holders are James Charles Hays (Director, 1.98Mn shares), Corp Westaim (TenPercentOwner, 1.92Mn shares), James Charles Hays (Director, 669.31K shares).
| # | Insider | Position | Direct | Indirect | Total | Share of Insiders | Last Filed |
|---|---|---|---|---|---|---|---|
| 1 | Corp Westaim | TenPercentOwner | 1,919,639 | 0 | 1,919,639 | 62.3% | 13 May, 2024 |
| 2 | David Christopher Ben Ibeson | Ceo Apollo | 266,867 | 79,708 | 346,575 | 11.3% | 05 Jan, 2026 |
| 3 | Andrew S Robinson | Chairman Ceo, Skyward Group | 179,894 | 0 | 179,894 | 5.8% | 08 May, 2026 |
| 4 | James Charles Hays | Director | 175,858 | 0 | 175,858 | 5.7% | 07 May, 2026 |
| 5 | Mark W Haushill | Cfo Skyward Group | 139,466 | 0 | 139,466 | 4.5% | 08 May, 2026 |
| 6 | James Richard Slaughter | Cuo Apollo | 55,475 | 12,724 | 68,199 | 2.2% | 05 Jan, 2026 |
| 7 | Robert E. Creager | Director | 54,830 | 0 | 54,830 | 1.8% | 07 May, 2026 |
| 8 | John A Iii Burkhart | President, Us Pc | 37,736 | 0 | 37,736 | 1.2% | 08 May, 2026 |
| 9 | Dan Pk Bodnar | Chief Information Officer | 28,147 | 0 | 28,147 | 0.9% | 08 May, 2026 |
| 10 | Leslie Shaunty | General Counsel Secretary | 26,104 | 0 | 26,104 | 0.8% | 10 Mar, 2025 |
| 11 | Sean W Duffy | Evp Chief Claims Officer | 20,097 | 0 | 20,097 | 0.7% | 08 May, 2026 |
| 12 | Sandip A Kapadia | Head Of Actuarial | 18,353 | 0 | 18,353 | 0.6% | 08 May, 2026 |
| 13 | Anthony J Kuczinski | Director | 15,977 | 0 | 15,977 | 0.5% | 21 May, 2026 |
| 14 | Thomas N Schmitt | Cpo, Skyward Group | 10,353 | 0 | 10,353 | 0.3% | 15 Jun, 2026 |
| 15 | Marcia A Dall | Director | 8,433 | 0 | 8,433 | 0.3% | 09 May, 2025 |
| 16 | Kirby Hill | Chairman, Captives Programs | 8,249 | 0 | 8,249 | 0.3% | 15 May, 2025 |
| 17 | Katharine Terry | Director | 6,780 | 0 | 6,780 | 0.2% | 09 May, 2025 |
| 18 | Gena L Ashe | Director | 4,570 | 0 | 4,570 | 0.1% | 12 May, 2026 |
| 19 | Michael J. Morrissey | Director | 3,519 | 0 | 3,519 | 0.1% | 09 May, 2025 |
| 20 | Chase M Clark | Chief Underwriting Officer | 3,279 | 0 | 3,279 | 0.1% | 10 Mar, 2025 |
| 21 | Christopher Locke Peirce | Director | 3,200 | 0 | 3,200 | 0.1% | 03 Mar, 2026 |
| 22 | Taryn Leonie Mcharg | Cfo Apollo | 0 | 100 | 100 | 0.0% | 03 Mar, 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 |
|---|---|---|---|---|---|---|---|---|
| 06 Aug, 2026 | Peter C Hearn | Director | Acquired A | 1,845 | $0.00 | $0 | 1,845 | Direct |
| 12 Jun, 2026 | Thomas N Schmitt | Cpo, Skyward Group | Disposed S | 8,397 | $51.32 | $430.96K | 10,353 | Direct |
| 21 May, 2026 | Anthony J Kuczinski | Director | Acquired P | 200 | $47.00 | $9.40K | 14,177 | Direct |
| 21 May, 2026 | Anthony J Kuczinski | Director | Acquired P | 800 | $47.00 | $37.60K | 14,977 | Direct |
| 21 May, 2026 | Anthony J Kuczinski | Director | Acquired P | 1,000 | $47.20 | $47.20K | 15,977 | Direct |
| 11 May, 2026 | Gena L Ashe | Director | Acquired M | 1,797 | — | — | 5,310 | Direct |
| 11 May, 2026 | Gena L Ashe | Director | Disposed S | 100 | $46.35 | $4.64K | 5,210 | Direct |
| 11 May, 2026 | Gena L Ashe | Director | Disposed S | 140 | $46.35 | $6.49K | 5,070 | Direct |
| 11 May, 2026 | Gena L Ashe | Director | Disposed S | 500 | $46.35 | $23.18K | 4,570 | Direct |
| 11 May, 2026 | Gena L Ashe | Director | Disposed M | 1,797 | $0.00 | $0 | 0 | Direct |
| 07 May, 2026 | Anthony J Kuczinski | Director | Acquired M | 1,797 | — | — | 13,977 | Direct |
| 06 May, 2026 | Mark W Haushill | Cfo Skyward Group | Acquired M | 5,036 | $0.00 | $0 | 141,448 | Direct |
| 06 May, 2026 | Dan Pk Bodnar | Chief Information Officer | Acquired M | 2,686 | $0.00 | $0 | 29,151 | Direct |
| 06 May, 2026 | John A Iii Burkhart | President, Us Pc | Acquired M | 4,813 | $0.00 | $0 | 39,630 | Direct |
| 06 May, 2026 | Andrew S Robinson | Chairman Ceo, Skyward Group | Acquired M | 20,150 | $0.00 | $0 | 187,824 | Direct |
| 06 May, 2026 | Sandip A Kapadia | Head Of Actuarial | Acquired M | 2,686 | $0.00 | $0 | 19,727 | Direct |
| 06 May, 2026 | Sean W Duffy | Evp Chief Claims Officer | Acquired M | 3,805 | $0.00 | $0 | 21,768 | Direct |
| 06 May, 2026 | Thomas N Schmitt | Cpo, Skyward Group | Acquired M | 3,358 | $0.00 | $0 | 19,881 | Direct |
| 06 May, 2026 | Andrew S Robinson | Chairman Ceo, Skyward Group | Disposed F | 7,930 | $43.68 | $346.38K | 179,894 | Direct |
| 06 May, 2026 | Mark W Haushill | Cfo Skyward Group | Disposed F | 1,982 | $43.68 | $86.57K | 139,466 | Direct |