SKWD · Insider Trading
Skyward Specialty Insurance Group, Inc. Common Stock
Every open-market purchase and sale reported by SKWD officers, directors and 10%+ beneficial owners on SEC Form 4, which must be filed within two business days of the transaction. Sales often reflect scheduled 10b5-1 plans or tax withholding rather than a directional view, so read counts alongside the size and the filer.
| Filed | Insider | Role | Type | Shares | Value |
|---|---|---|---|---|---|
| 2026-08-07 | Peter C Hearn | Director | A | +1,845 deriv. | — |
| 2026-08-07 | Peter C Hearn | Director | A | +1,845 deriv. | — |
| 2026-06-15 | Thomas N Schmitt | CPO, Skyward Group | Sell | −8,397 | −$430.96K |
| 2026-05-21 | Anthony J Kuczinski | Director | Buy | +2,000 | +$94.20K |
| 2026-05-12 | Gena L Ashe | Director | MIXED | +1,057 | −$34.30K |
| 2026-05-08 | Katharine Terry | Director | A | — | — |
| 2026-05-08 | Michael J. Morrissey | Director | A | — | — |
| 2026-05-08 | Marcia A Dall | Director | A | — | — |
| 2026-05-08 | Andrew S Robinson | Chairman & CEO, Skyward Group | MIXED | +12,220 | −$346.38K |
| 2026-05-08 | Sandip A Kapadia | Head of Actuarial | MIXED | +1,312 | −$60.02K |
| 2026-05-08 | Christopher Locke Peirce | Director | A | — | — |
| 2026-05-08 | Mark W Haushill | CFO - Skyward Group | MIXED | +3,054 | −$86.57K |
| 2026-05-08 | Gena L Ashe | Director | A | — | — |
| 2026-05-08 | Sean W Duffy | EVP & Chief Claims Officer | MIXED | +2,134 | −$72.99K |
| 2026-05-08 | John A Burkhart III | President, US P&C | MIXED | +2,919 | −$82.73K |
| 2026-05-08 | Anthony J Kuczinski | Director | M | +1,797 | — |
| 2026-05-08 | Thomas N Schmitt | CPO, Skyward Group | MIXED | +2,036 | −$57.74K |
| 2026-05-08 | Dan PK Bodnar | Chief Information Officer | MIXED | +1,682 | −$43.85K |
| 2026-05-07 | Robert E. Creager | Director | M | +1,797 | — |
| 2026-05-07 | James Charles Hays | Director | M | +1,797 | — |
| 2026-03-04 | Anthony J Kuczinski | Director | Buy | +5,000 | +$239.46K |
| 2026-03-03 | Christopher Locke Peirce | Director | Buy | +3,200 | +$151.36K |
| 2026-03-03 | Taryn Leonie McHarg | CFO - Apollo | Buy | +200 | +$9.32K |
| 2026-02-27 | James Richard Slaughter | CUO - Apollo | A | — | — |
| 2026-02-27 | Thomas N Schmitt | CPO, Skyward Group | MIXED | +1,776 | −$52.91K |
| 2026-02-27 | Patricia A. Ryan | Chief Legal Officer | A | +15,141 deriv. | — |
| 2026-02-27 | David Christopher Ben Ibeson | CEO - Apollo | A | — | — |
| 2026-02-27 | Dan PK Bodnar | Chief Information Officer | MIXED | +1,467 | −$40.20K |
| 2026-02-27 | Shakoor Khan | Corp. Dev. Officer | A | — | — |
| 2026-02-27 | Sean W Duffy | EVP & Chief Claims Officer | MIXED | +1,927 | −$63.83K |
| 2026-02-27 | John A Burkhart III | President, US P&C | MIXED | +2,546 | −$75.81K |
| 2026-02-27 | Taryn Leonie McHarg | CFO - Apollo | A | — | — |
| 2026-02-27 | Andrew S Robinson | Chairman & CEO, Skyward Group | Buy | +22,100 | +$1.03M |
| 2026-02-27 | Sandip A Kapadia | Head of Actuarial | MIXED | +1,496 | −$38.87K |
| 2026-02-27 | Mark W Haushill | EVP & CFO, Skyward Group | MIXED | +2,956 | −$65.90K |
| 2026-02-27 | Andrew S Robinson | Chairman & CEO, Skyward Group | MIXED | +10,659 | −$317.38K |
| 2026-02-10 | Thomas N Schmitt | CPO, Skyward Group | Sell | −2,616 | −$113.77K |
| 2026-01-14 | Thomas N Schmitt | CPO, Skyward Group | MIXED | +5,883 | −$189.79K |
| 2026-01-14 | Sean W Duffy | EVP & Chief Claims Officer | MIXED | +5,629 | −$201.50K |
| 2026-01-14 | Andrew S Robinson | Chairman & CEO, Skyward Group | MIXED | +60,468 | −$1.82M |
| 2026-01-14 | John A Burkhart III | President, US P&C, Skyward Grp | MIXED | +7,909 | −$249.91K |
| 2026-01-14 | Sandip A Kapadia | Head of Actuarial | MIXED | +6,207 | −$174.86K |
| 2026-01-14 | Dan PK Bodnar | Chief Information Officer | MIXED | +6,083 | −$180.57K |
| 2026-01-14 | Andrew S Robinson | Chairman & CEO, Skyward Group | — | — | — |
| 2026-01-14 | Mark W Haushill | EVP & CFO, Skyward Group | MIXED | +7,910 | −$249.86K |
| 2026-01-05 | Taryn Leonie McHarg | CFO - Apollo | A | +7,764 | +$388.20K |
| 2026-01-05 | James Charles Hays | Director | A | +143,664 | +$7.18M |
| 2026-01-05 | Dan PK Bodnar | CHIEF INFORMATION OFFICER | MIXED | +1,255 | −$39.10K |
| 2026-01-05 | Sandip A Kapadia | Head of Actuarial | MIXED | +1,279 | −$37.87K |
| 2026-01-05 | Andrew S Robinson | Chairman & CEO, Skyward Group | MIXED | +9,178 | −$305.28K |
| Insider | Role | Shares Held | Value |
|---|---|---|---|
| James Charles Hays | Director | 845,169 | $51.23M |
| David Christopher Ben Ibeson | CEO - Apollo | 346,575 | $21.01M |
| Andrew S Robinson | Chairman & CEO, Skyward Group | 187,824 | $11.39M |
| Mark W Haushill | CFO - Skyward Group | 139,466 | $8.45M |
| James Richard Slaughter | CUO - Apollo | 68,199 | $4.13M |
| Robert E. Creager | Director | 54,830 | $3.32M |
| John A Burkhart III | President, US P&C | 37,736 | $2.29M |
| Dan PK Bodnar | Chief Information Officer | 28,147 | $1.71M |
| Leslie Shaunty | GENERAL COUNSEL & SECRETARY | 22,516 | $1.36M |
| Sean W Duffy | EVP & Chief Claims Officer | 20,097 | $1.22M |
| Sandip A Kapadia | Head of Actuarial | 19,727 | $1.20M |
| Anthony J Kuczinski | Director | 16,002 | $970.04K |
| Thomas N Schmitt | CPO, Skyward Group | 10,353 | $627.60K |
| Marcia A Dall | Director | 8,433 | $511.21K |
| Kirby Hill | Chairman, Captives & Programs | 8,249 | $500.05K |
| Taryn Leonie McHarg | CFO - Apollo | 7,864 | $476.72K |
| Katharine Terry | Director | 6,780 | $411.00K |
| Gena L Ashe | Director | 5,310 | $321.89K |
| Michael J. Morrissey | Director | 3,519 | $213.32K |
| Christopher Locke Peirce | Director | 3,200 | $193.98K |
| Chase M Clark | Chief Underwriting Officer | 1,880 | $113.97K |
| Shakoor Khan | Corp. Dev. Officer | 694 | $42.07K |
Form 4 reports a change in beneficial ownership by an officer, director or 10%+ holder, and must be filed within two business days of the transaction — so this is close to real time, unlike the 45-day-lagged 13F institutional data.
Transaction codes matter more than the raw buy/sell count. Code P is an open-market purchase — an insider choosing to buy with their own money, which is the signal most research treats as informative. Code S is a sale, but sales are frequently pre-scheduled under a 10b5-1 plan or cover tax withholding on vesting equity, so a run of sales often says nothing directional. Codes A and M are grants and option exercises rather than open-market decisions.
Full filing history and per-insider positions are on the SKWD quote page; the site-wide leaderboard is on the insider transactions hub.
Market data may be delayed, incomplete, or inaccurate. Not a recommendation to buy, sell, or hold any security. Verify quotes with your broker before trading. See Terms §17.