Thomas N. Schmitt, CPO of Skyward Group, made two open market sales of Skyward Specialty Insurance Group ($SKWD) shares totaling about $118 thousand over the past year. His most recent sale occurred on February 9, 2026. These sales rank 9,331st among 11,678 individual insiders, well below the average sale amount of $8.6 million across 6.4 transactions per insider. Schmitt made no open market purchases in this period.
| Transaction Date | Company | Ticker | Insider Name | Title | Transaction Type | Security | Shares | Price | Shares Owned Following | Total Shares Outstanding | % of Owned | % of Outstanding |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Feb. 25, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CPO, Skyward Group | M | Common Stock | 2929 | $0.00 | 17,676.0000 | 41,868,449 | 19.86% | 0.01% |
| Feb. 25, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CPO, Skyward Group | A | 2026 LTIP - RSUs | 1442 | $0.00 | 1,442.0000 | 41,868,449 | 9999.99% | 0.00% |
| Feb. 25, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CPO, Skyward Group | A | 2026 LTIP - PSUs | 1442 | $0.00 | 1,442.0000 | 41,868,449 | 9999.99% | 0.00% |
| Feb. 25, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CPO, Skyward Group | A | 2026 LTIP - PSUs | 1442 | $0.00 | 1,442.0000 | 41,868,449 | 9999.99% | 0.00% |
| Feb. 26, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CPO, Skyward Group | F | Common Stock | 1153 | $45.89 | 16,523.0000 | 41,868,449 | 6.52% | 0.00% |
| Feb. 25, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CPO, Skyward Group | M | 2023 LTIP - PSUs | 2525 | $0.00 | 0.0000 | 41,868,449 | 100.00% | 0.01% |
| Feb. 9, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CPO, Skyward Group | S | Common Stock | 2616 | $43.49 | 14,747.0000 | 41,868,449 | 15.07% | 0.01% |
| Jan. 12, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CPO, Skyward Group | M | Common Stock | 5000 | $0.00 | 19,331.0000 | 41,868,449 | 34.89% | 0.01% |
| Jan. 12, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CPO, Skyward Group | M | Common Stock | 5000 | $0.00 | 16,480.0000 | 41,868,449 | 43.55% | 0.01% |
| Jan. 12, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CPO, Skyward Group | M | 2023 IPO RSU Grant (3-Year) | 5000 | $0.00 | 0.0000 | 41,868,449 | 100.00% | 0.01% |
| Jan. 12, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CPO, Skyward Group | M | 2023 IPO RSU Grant (4-Year) | 5000 | $0.00 | 5,000.0000 | 41,868,449 | 50.00% | 0.01% |
| Jan. 12, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CPO, Skyward Group | F | Common Stock | 1968 | $46.10 | 17,363.0000 | 41,868,449 | 10.18% | 0.00% |
| Jan. 12, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CPO, Skyward Group | F | Common Stock | 2149 | $46.10 | 14,331.0000 | 41,868,449 | 13.04% | 0.01% |
| Jan. 1, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CPO, Skyward Group | F | Common Stock | 1004 | $51.11 | 11,480.0000 | 41,868,449 | 8.04% | 0.00% |
| Jan. 1, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CPO, Skyward Group | M | Common Stock | 2525 | $0.00 | 12,484.0000 | 41,868,449 | 25.35% | 0.01% |
| Jan. 1, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CPO, Skyward Group | M | 2023 LTIP - RSUs | 2525 | $0.00 | 0.0000 | 41,868,449 | 100.00% | 0.01% |
| Dec. 11, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CHIEF PEOPLE & ADMIN.OFFICER | S | Common Stock | 88 | $47.61 | 9,959.0000 | 41,868,449 | 0.88% | 0.00% |
| March 6, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CHIEF PEOPLE & ADMIN. OFFICER | M | Common Stock | 4406 | $0.00 | 8,352.0000 | 41,377,460 | 111.66% | 0.01% |
| March 6, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CHIEF PEOPLE & ADMIN. OFFICER | S | Common Stock | 1697 | $50.24 | 6,655.0000 | 41,377,460 | 20.32% | 0.00% |
| March 6, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CHIEF PEOPLE & ADMIN. OFFICER | M | Common Stock | 5000 | $0.00 | 11,655.0000 | 41,377,460 | 75.13% | 0.01% |
| March 6, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CHIEF PEOPLE & ADMIN. OFFICER | S | Common Stock | 1928 | $50.24 | 9,727.0000 | 41,377,460 | 16.54% | 0.00% |
| March 6, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CHIEF PEOPLE & ADMIN. OFFICER | M | 2022 LTIP - PSUs | 4604 | $0.00 | 0.0000 | 41,377,460 | 100.00% | 0.01% |
| March 6, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CHIEF PEOPLE & ADMIN. OFFICER | M | 2023 IPO RSU Grant (3-Year) | 5000 | $0.00 | 5,000.0000 | 41,377,460 | 50.00% | 0.01% |
| March 3, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CHIEF PEOPLE & ADMIN. OFFICER | S | Common Stock | 6300 | $51.92 | 3,946.0000 | 41,377,460 | 61.49% | 0.02% |
| Feb. 25, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CHIEF PEOPLE & ADMIN. OFFICER | A | 2025 LTIP - RSUs | 1182 | $0.00 | 1,182.0000 | 41,377,460 | 9999.99% | 0.00% |
| Feb. 25, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CHIEF PEOPLE & ADMIN. OFFICER | A | 2025 LTIP - PSUs | 1182 | $0.00 | 1,182.0000 | 41,377,460 | 9999.99% | 0.00% |
| Feb. 25, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CHIEF PEOPLE & ADMIN. OFFICER | A | 2025 LTIP - PSUs | 1182 | $0.00 | 1,182.0000 | 41,377,460 | 9999.99% | 0.00% |
| Jan. 6, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CHIEF PEOPLE & ADMIN. OFFICER | S | Common Stock | 546 | $46.85 | 10,246.0000 | 41,377,460 | 5.06% | 0.00% |
| Jan. 3, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CHIEF PEOPLE & ADMIN. OFFICER | S | Common Stock | 637 | $47.81 | 10,792.0000 | 41,377,460 | 5.57% | 0.00% |
| Feb. 29, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CHIEF PEOPLE & ADMIN. OFFICER | M | Common Stock | 5333 | $0.00 | 12,709.0000 | 38,317,534 | 72.30% | 0.01% |
| Feb. 29, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CHIEF PEOPLE & ADMIN. OFFICER | M | 2021 LTIP - Performance Share Units | 5333 | $0.00 | 0.0000 | 38,317,534 | 100.00% | 0.01% |
| Feb. 27, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CHIEF PEOPLE & ADMIN. OFFICER | A | 2024 LTIP - Performance Share Units | 1495 | $0.00 | 1,495.0000 | 38,317,534 | 9999.99% | 0.00% |
| Feb. 27, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CHIEF PEOPLE & ADMIN. OFFICER | A | 2024 LTIP - Common Stock | 1495 | $0.00 | 1,495.0000 | 38,317,534 | 9999.99% | 0.00% |
| Feb. 29, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CHIEF PEOPLE & ADMIN. OFFICER | F | Common Stock | 1992 | $36.47 | 10,717.0000 | 38,317,534 | 15.67% | 0.01% |
| Jan. 1, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CHIEF PEOPLE & ADMIN. OFFICER | M | Restricted Stock Unit | 5281 | $0.00 | 0.0000 | 38,317,534 | 100.00% | 0.01% |
| Jan. 1, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CHIEF PEOPLE & ADMIN. OFFICER | M | Common Stock | 5281 | $0.00 | 9,610.0000 | 38,317,534 | 121.99% | 0.01% |
| Jan. 1, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Schmitt Thomas N | CHIEF PEOPLE & ADMIN. OFFICER | F | Common Stock | 2234 | $33.88 | 7,376.0000 | 38,317,534 | 23.25% | 0.01% |