| Date | Insider | Title | Code | Shares | Price | Value |
|---|---|---|---|---|---|---|
| Jun 12, 2026 | Schmitt Thomas N | CPO, Skyward Group | S | 8,397 | $51.3235 | $430.96K |
| May 21, 2026 | Kuczinski Anthony J | Director | P | 1,000 | $47.2000 | $47.20K |
| May 21, 2026 | Kuczinski Anthony J | Director | P | 800 | $47.0000 | $37.60K |
| May 21, 2026 | Kuczinski Anthony J | Director | P | 200 | $47.0000 | $9.40K |
| May 11, 2026 | Ashe Gena L | Director | M | 1,797 | $0.0000 | $0.00 |
| May 11, 2026 | Ashe Gena L | Director | S | 500 | $46.3500 | $23.18K |
| May 11, 2026 | Ashe Gena L | Director | S | 140 | $46.3500 | $6.49K |
| May 11, 2026 | Ashe Gena L | Director | S | 100 | $46.3500 | $4.63K |
| May 11, 2026 | Ashe Gena L | Director | M | 1,797 | – | – |
| May 7, 2026 | Kuczinski Anthony J | Director | M | 1,797 | $0.0000 | $0.00 |
| May 7, 2026 | Kuczinski Anthony J | Director | M | 1,797 | – | – |
| May 6, 2026 | Ashe Gena L | Director | A | 3,334 | $0.0000 | $0.00 |
| May 6, 2026 | Dall Marcia A | Director | A | 3,334 | $0.0000 | $0.00 |
| May 6, 2026 | Kuczinski Anthony J | Director | A | 3,334 | $0.0000 | $0.00 |
| May 6, 2026 | Morrissey Michael J. | Director | A | 3,334 | $0.0000 | $0.00 |
| May 6, 2026 | Peirce Christopher Locke | Director | A | 3,890 | $0.0000 | $0.00 |
| May 6, 2026 | Terry Katharine | Director | A | 3,334 | $0.0000 | $0.00 |
| May 6, 2026 | Duffy Sean W | EVP & Chief Claims Officer | M | 2,861 | $0.0000 | $0.00 |
| May 6, 2026 | Duffy Sean W | EVP & Chief Claims Officer | F | 1,671 | $43.6800 | $72.99K |
| May 6, 2026 | Duffy Sean W | EVP & Chief Claims Officer | M | 3,805 | $0.0000 | $0.00 |
| May 6, 2026 | Robinson Andrew S | Chairman & CEO, Skyward Group | M | 15,151 | $0.0000 | $0.00 |
| May 6, 2026 | Robinson Andrew S | Chairman & CEO, Skyward Group | F | 7,930 | $43.6800 | $346.38K |
| May 6, 2026 | Robinson Andrew S | Chairman & CEO, Skyward Group | M | 20,150 | $0.0000 | $0.00 |
| May 6, 2026 | HAUSHILL MARK W | CFO - Skyward Group | M | 3,787 | $0.0000 | $0.00 |
| May 6, 2026 | HAUSHILL MARK W | CFO - Skyward Group | F | 1,982 | $43.6800 | $86.57K |
| May 6, 2026 | HAUSHILL MARK W | CFO - Skyward Group | M | 5,036 | $0.0000 | $0.00 |
| May 6, 2026 | Burkhart John A III | President, US P&C | M | 3,619 | $0.0000 | $0.00 |
| May 6, 2026 | Burkhart John A III | President, US P&C | F | 1,894 | $43.6800 | $82.73K |
| May 6, 2026 | Burkhart John A III | President, US P&C | M | 4,813 | $0.0000 | $0.00 |
| May 6, 2026 | Bodnar Dan PK | Chief Information Officer | M | 2,020 | $0.0000 | $0.00 |
| May 6, 2026 | Bodnar Dan PK | Chief Information Officer | F | 1,004 | $43.6800 | $43.85K |
| May 6, 2026 | Bodnar Dan PK | Chief Information Officer | M | 2,686 | $0.0000 | $0.00 |
| May 6, 2026 | Kapadia Sandip A | Head of Actuarial | M | 2,020 | $0.0000 | $0.00 |
| May 6, 2026 | Kapadia Sandip A | Head of Actuarial | F | 1,374 | $43.6800 | $60.02K |
| May 6, 2026 | Kapadia Sandip A | Head of Actuarial | M | 2,686 | $0.0000 | $0.00 |
| May 6, 2026 | Schmitt Thomas N | CPO, Skyward Group | M | 2,525 | $0.0000 | $0.00 |
| May 6, 2026 | Schmitt Thomas N | CPO, Skyward Group | F | 1,322 | $43.6800 | $57.74K |
| May 6, 2026 | Schmitt Thomas N | CPO, Skyward Group | M | 3,358 | $0.0000 | $0.00 |
| May 5, 2026 | Creager Robert E. | Director | M | 1,797 | $0.0000 | $0.00 |
| May 5, 2026 | Creager Robert E. | Director | M | 1,797 | – | – |
| May 5, 2026 | Hays James Charles | Director | M | 1,797 | $0.0000 | $0.00 |
| May 5, 2026 | Hays James Charles | Director | M | 1,797 | – | – |
| Mar 3, 2026 | Kuczinski Anthony J | Director | P | 1,000 | $48.1321 | $48.13K |
| Mar 2, 2026 | Peirce Christopher Locke | Director | P | 3,200 | $47.3000 | $151.36K |
| Mar 2, 2026 | Kuczinski Anthony J | Director | P | 2,000 | $48.7911 | $97.58K |
| Feb 27, 2026 | Robinson Andrew S | Chairman & CEO, Skyward Group | P | 11,279 | $46.9400 | $529.44K |
| Feb 27, 2026 | Robinson Andrew S | Chairman & CEO, Skyward Group | P | 10,821 | $46.5700 | $503.93K |
| Feb 27, 2026 | McHarg Taryn Leonie | CFO - Apollo | P | 100 | $46.4900 | $4.65K |
| Feb 27, 2026 | McHarg Taryn Leonie | CFO - Apollo | P | 100 | $46.7100 | $4.67K |
| Feb 27, 2026 | Kuczinski Anthony J | Director | P | 2,000 | $46.8751 | $93.75K |