As of the latest Form 4 filed Jun 15, 2026.
What Skyward Specialty Insurance Group, Inc. Common Stock insiders — officers, directors and 10% owners — have bought and sold in their own stock, straight from their SEC Form 4 filings. Values are shares × the reported transaction price where both are disclosed.
Buys plotted up, sells down; bar height is the disclosed dollar value (shares × reported price). Our Form 4 history is only complete from mid-2026, so early months are sparse — the series fills in as more filings land. Open-market purchases and sales only.
Newest filing first — the 33 most recent filings for SKWD.
| Filed | Trade date | Insider | Transaction | Shares | Price | Value | 10b5-1 | Filing |
|---|---|---|---|---|---|---|---|---|
| 2026-06-15 | 2026-06-12 | Schmitt Thomas N CPO, Skyward Group | SSale | −8.40K | $51.32 | $431K | No | Form 4 ↗ |
| 2026-05-07 | 2026-05-05 | Hays James Charles Director | MExercise | +1.80K | — | — | No | Form 4 ↗ |
| 2026-05-07 | 2026-05-05 | Creager Robert E. Director | MExercise | +1.80K | — | — | No | Form 4 ↗ |
| 2026-01-14 | 2026-01-12 | Bodnar Dan PK Chief Information Officer | FTax | −1.87K | $46.10 | $86.1K | No | Form 4 ↗ |
| 2026-01-14 | 2026-01-12 | Bodnar Dan PK, Chief Information Officer | MExercise | +5.00K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-01-14 | 2026-01-12 | Bodnar Dan PK, Chief Information Officer | FTax | −2.05K | $46.10 | $94.5K | No | Form 4 ↗ |
| 2026-01-14 | 2026-01-12 | Bodnar Dan PK, Chief Information Officer | MExercise | +5.00K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-01-14 | 2026-01-12 | Schmitt Thomas N CPO, Skyward Group | FTax | −1.97K | $46.10 | $90.7K | No | Form 4 ↗ |
| 2026-01-14 | 2026-01-12 | Schmitt Thomas N, CPO, Skyward Group | MExercise | +5.00K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-01-14 | 2026-01-12 | Schmitt Thomas N, CPO, Skyward Group | FTax | −2.15K | $46.10 | $99.1K | No | Form 4 ↗ |
| 2026-01-14 | 2026-01-12 | Schmitt Thomas N, CPO, Skyward Group | MExercise | +5.00K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-01-14 | 2026-01-12 | Kapadia Sandip A Head of Actuarial | FTax | −1.81K | $46.10 | $83.3K | No | Form 4 ↗ |
| 2026-01-14 | 2026-01-12 | Kapadia Sandip A, Head of Actuarial | MExercise | +5.00K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-01-14 | 2026-01-12 | Kapadia Sandip A, Head of Actuarial | FTax | −1.99K | $46.10 | $91.5K | No | Form 4 ↗ |
| 2026-01-14 | 2026-01-12 | Kapadia Sandip A, Head of Actuarial | MExercise | +5.00K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-01-14 | 2026-01-12 | Burkhart John A III President, US P&C, Skyward Grp | FTax | −2.62K | $46.10 | $121K | No | Form 4 ↗ |
| 2026-01-14 | 2026-01-12 | Burkhart John A III, President, US P&C, Skyward Grp | MExercise | +6.67K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-01-14 | 2026-01-12 | Burkhart John A III, President, US P&C, Skyward Grp | FTax | −2.80K | $46.10 | $129K | No | Form 4 ↗ |
| 2026-01-14 | 2026-01-12 | Burkhart John A III, President, US P&C, Skyward Grp | MExercise | +6.67K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-01-14 | 2026-01-12 | Duffy Sean W EVP & Chief Claims Officer | FTax | −2.10K | $46.10 | $96.6K | No | Form 4 ↗ |
| 2026-01-14 | 2026-01-12 | Duffy Sean W, EVP & Chief Claims Officer | MExercise | +5.00K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-01-14 | 2026-01-12 | Duffy Sean W, EVP & Chief Claims Officer | FTax | −2.28K | $46.10 | $105K | No | Form 4 ↗ |
| 2026-01-14 | 2026-01-12 | Duffy Sean W, EVP & Chief Claims Officer | MExercise | +5.00K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-01-14 | 2026-01-12 | Robinson Andrew S Chairman & CEO, Skyward Group | FTax | −19.7K | $46.10 | $907K | No | Form 4 ↗ |
| 2026-01-14 | 2026-01-12 | Robinson Andrew S, Chairman & CEO, Skyward Group | MExercise | +50.0K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-01-14 | 2026-01-12 | Robinson Andrew S, Chairman & CEO, Skyward Group | FTax | −19.9K | $46.10 | $915K | No | Form 4 ↗ |
| 2026-01-14 | 2026-01-12 | Robinson Andrew S, Chairman & CEO, Skyward Group | MExercise | +50.0K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-01-14 | 2026-01-12 | HAUSHILL MARK W EVP & CFO, Skyward Group | FTax | −2.62K | $46.10 | $121K | No | Form 4 ↗ |
| 2026-01-14 | 2026-01-12 | HAUSHILL MARK W, EVP & CFO, Skyward Group | MExercise | +6.67K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2026-01-14 | 2026-01-12 | HAUSHILL MARK W, EVP & CFO, Skyward Group | FTax | −2.80K | $46.10 | $129K | No | Form 4 ↗ |
| 2026-01-14 | 2026-01-12 | HAUSHILL MARK W, EVP & CFO, Skyward Group | MExercise | +6.67K | $0.00 | $0.00 | No | Form 4 ↗ |
| 2025-12-19 | 2025-12-18 | Kapadia Sandip A Head of Actuarial | SSale | −5.03K | $50.01 | $252K | Yes (planned) | Form 4 ↗ |
| 2025-12-11 | 2025-12-11 | Schmitt Thomas N CHIEF PEOPLE & ADMIN.OFFICER | SSale | −88.00 | $47.61 | $4.19K | Yes (planned) | Form 4 ↗ |
Insiders — a company’s officers, directors and holders of more than 10% of its stock — must report any trade in that stock to the SEC on a Form 4 within two business days. Each row here is one transaction from those filings.
The transaction code tells you what happened: Purchase (P) and Sale (S) are open-market trades — the ones markets watch most; Award (A) is a granted stock or unit, Option exercise (M) converts options into shares, and Gift (G) is a transfer for no consideration. Awards, exercises and gifts are largely compensation or administrative, not a directional bet.
One caveat on sales: many are made under a Rule 10b5-1 plan scheduled months in advance, so a sale is not automatically a bearish signal. Insider activity is a noisy input — read it alongside the filings, not on its own.
See also SKWD’s full analysis or the market-wide insider trading feed. The tabs above jump to SKWD’s other SEC data.
Source: SEC Form 4 filings for SKWD, parsed from EDGAR. Transaction prices are as reported in the filing — SEC public-domain data, not market quotes. Values are shares × reported price where both are disclosed; grants and gifts often carry no price. A delayed record of what insiders reported, not a live position or a recommendation.
Research and education only — not financial advice. TENKis not a registered investment adviser or broker-dealer and gives no personalized advice. Every call is impersonal — identical for all users, generated on a schedule from SEC filings plus a delayed/third-party price feed — may be wrong or out of date, and is not a recommendation to buy or sell any security. The operator and an affiliated trading operation may hold or trade the securities TENK rates; see Disclosures. Past performance does not guarantee future results. Do your own research.