21 insiders reported 154 Form 4 transactions for Skyward Specialty Insurance Group, Inc. (SKWD) over the past 18 months (most recent 2026-05-21). Recent activity: Kuczinski Anthony J (Director) Buy 200 shares, Kuczinski Anthony J (Director) Buy 800 shares, Kuczinski Anthony J (Director) Buy 1,000 shares, Ashe Gena L (Director) Buy 1,797 shares, Ashe Gena L (Director) Sell 100 shares. Source: SEC Form 4.
| Date | Insider | Title | Type | Shares | Value |
|---|---|---|---|---|---|
| 2026-05-21 | Kuczinski Anthony J | Director | Buy | 200 | $9,400 |
| 2026-05-21 | Kuczinski Anthony J | Director | Buy | 800 | $37,600 |
| 2026-05-21 | Kuczinski Anthony J | Director | Buy | 1,000 | $47,200 |
| 2026-05-12 | Ashe Gena L | Director | Buy | 1,797 | $0 |
| 2026-05-12 | Ashe Gena L | Director | Sell | 100 | $4,635 |
| 2026-05-12 | Ashe Gena L | Director | Sell | 140 | $6,489 |
| 2026-05-12 | Ashe Gena L | Director | Sell | 500 | $23,175 |
| 2026-05-08 | Duffy Sean W | EVP & Chief Claims Officer | Buy | 3,805 | $0 |
| 2026-05-08 | Burkhart John A III | President, US P&C | Buy | 4,813 | $0 |
| 2026-05-08 | Kapadia Sandip A | Head of Actuarial | Buy | 2,686 | $0 |
| 2026-05-08 | Bodnar Dan PK | Chief Information Officer | Buy | 2,686 | $0 |
| 2026-05-08 | Kuczinski Anthony J | Director | Buy | 1,797 | $0 |
| 2026-05-08 | Schmitt Thomas N | CPO, Skyward Group | Buy | 3,358 | $0 |
| 2026-05-08 | Robinson Andrew S | Chairman & CEO, Skyward Group | Buy | 20,150 | $0 |
| 2026-05-08 | HAUSHILL MARK W | CFO - Skyward Group | Buy | 5,036 | $0 |
| 2026-05-08 | Kapadia Sandip A | Head of Actuarial | Sell | 1,374 | $60,016 |
| 2026-05-08 | Duffy Sean W | EVP & Chief Claims Officer | Sell | 1,671 | $72,989 |
| 2026-05-08 | Schmitt Thomas N | CPO, Skyward Group | Sell | 1,322 | $57,745 |
| 2026-05-08 | Bodnar Dan PK | Chief Information Officer | Sell | 1,004 | $43,855 |
| 2026-05-08 | Robinson Andrew S | Chairman & CEO, Skyward Group | Sell | 7,930 | $346,382 |
| 2026-05-08 | HAUSHILL MARK W | CFO - Skyward Group | Sell | 1,982 | $86,574 |
| 2026-05-08 | Burkhart John A III | President, US P&C | Sell | 1,894 | $82,730 |
| 2026-05-07 | Creager Robert E. | Director | Buy | 1,797 | $0 |
| 2026-05-07 | Hays James Charles | Director | Buy | 1,797 | $0 |
| 2026-03-04 | Kuczinski Anthony J | Director | Buy | 2,000 | $93,760 |
Source: SEC Form 4 filings · as of 2026-05-21