Sean W. Duffy, EVP and Chief Claims Officer at Skyward Specialty Insurance Group ($SKWD), made one open market sale of common shares in the last year, totaling $275 thousand. His most recent sale occurred on March 17, 2025. These sales rank 7,747th among 11,678 individual insiders in our database, where the average is $8.6 million across about 6.4 transactions. Duffy made no open market purchases during 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 | Duffy Sean W | EVP & Chief Claims Officer | M | Common Stock | 3318 | $0.00 | 19,354.0000 | 41,868,449 | 20.69% | 0.01% |
| Feb. 25, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Duffy Sean W | EVP & Chief Claims Officer | A | 2026 Bright Future - RSUs | 4326 | $0.00 | 4,326.0000 | 41,868,449 | 9999.99% | 0.01% |
| Feb. 25, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Duffy Sean W | EVP & Chief Claims Officer | 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 | Duffy Sean W | EVP & Chief Claims Officer | 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 | Duffy Sean W | EVP & Chief Claims Officer | M | 2023 LTIP - PSUs | 2861 | $0.00 | 0.0000 | 41,868,449 | 100.00% | 0.01% |
| Feb. 26, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Duffy Sean W | EVP & Chief Claims Officer | F | Common Stock | 1391 | $45.89 | 17,963.0000 | 41,868,449 | 7.19% | 0.00% |
| Jan. 12, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Duffy Sean W | EVP & Chief Claims Officer | F | Common Stock | 2276 | $46.10 | 13,131.0000 | 41,868,449 | 14.77% | 0.01% |
| Jan. 12, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Duffy Sean W | EVP & Chief Claims Officer | 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 | Duffy Sean W | EVP & Chief Claims Officer | 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 | Duffy Sean W | EVP & Chief Claims Officer | F | Common Stock | 2095 | $46.10 | 16,036.0000 | 41,868,449 | 11.55% | 0.01% |
| Jan. 12, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Duffy Sean W | EVP & Chief Claims Officer | M | Common Stock | 5000 | $0.00 | 18,131.0000 | 41,868,449 | 38.08% | 0.01% |
| Jan. 12, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Duffy Sean W | EVP & Chief Claims Officer | M | Common Stock | 5000 | $0.00 | 15,407.0000 | 41,868,449 | 48.04% | 0.01% |
| Jan. 1, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Duffy Sean W | EVP & CHIEF CLAIMS OFFICER | F | Common Stock | 1267 | $51.11 | 10,407.0000 | 41,868,449 | 10.85% | 0.00% |
| Jan. 1, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Duffy Sean W | EVP & CHIEF CLAIMS OFFICER | M | 2023 LTIP - RSUs | 2861 | $0.00 | 0.0000 | 41,868,449 | 100.00% | 0.01% |
| Jan. 1, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Duffy Sean W | EVP & CHIEF CLAIMS OFFICER | M | Common Stock | 2861 | $0.00 | 11,674.0000 | 41,868,449 | 32.46% | 0.01% |
| March 17, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Duffy Sean W | EVP & CHIEF CLAIMS OFFICER | S | Common Stock | 5625 | $48.90 | 8,813.0000 | 41,377,460 | 38.96% | 0.01% |
| March 6, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Duffy Sean W | EVP & CHIEF CLAIMS OFFICER | M | 2023 IPO RSU Grant (3-Year) | 5000 | $0.00 | 5,000.0000 | 41,377,460 | 50.00% | 0.01% |
| March 6, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Duffy Sean W | EVP & CHIEF CLAIMS OFFICER | M | Common Stock | 4993 | $0.00 | 13,448.0000 | 41,377,460 | 59.05% | 0.01% |
| March 6, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Duffy Sean W | EVP & CHIEF CLAIMS OFFICER | S | Common Stock | 2002 | $50.24 | 11,446.0000 | 41,377,460 | 14.89% | 0.00% |
| March 6, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Duffy Sean W | EVP & CHIEF CLAIMS OFFICER | M | Common Stock | 5000 | $0.00 | 16,446.0000 | 41,377,460 | 43.68% | 0.01% |
| March 6, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Duffy Sean W | EVP & CHIEF CLAIMS OFFICER | S | Common Stock | 2008 | $50.24 | 14,438.0000 | 41,377,460 | 12.21% | 0.00% |
| March 6, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Duffy Sean W | EVP & CHIEF CLAIMS OFFICER | M | 2022 LTIP - PSUs | 4993 | $0.00 | 0.0000 | 41,377,460 | 100.00% | 0.01% |
| Feb. 25, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Duffy Sean W | EVP & CHIEF CLAIMS OFFICER | A | 2025 LTIP - PSUs | 1351 | $0.00 | 1,351.0000 | 41,377,460 | 9999.99% | 0.00% |
| Feb. 25, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Duffy Sean W | EVP & CHIEF CLAIMS OFFICER | A | 2025 LTIP - PSUs | 1351 | $0.00 | 1,351.0000 | 41,377,460 | 9999.99% | 0.00% |
| Feb. 25, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Duffy Sean W | EVP & CHIEF CLAIMS OFFICER | A | 2025 LTIP - RSUs | 1351 | $0.00 | 1,351.0000 | 41,377,460 | 9999.99% | 0.00% |
| Jan. 2, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Duffy Sean W | EVP & CHIEF CLAIMS OFFICER | S | Common Stock | 1475 | $49.02 | 8,455.0000 | 41,377,460 | 14.85% | 0.00% |
| Feb. 27, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Duffy Sean W | EVP & CHIEF CLAIMS OFFICER | A | 2024 LTIP - Common Stock | 1745 | $0.00 | 1,745.0000 | 38,317,534 | 9999.99% | 0.00% |
| Feb. 27, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Duffy Sean W | EVP & CHIEF CLAIMS OFFICER | A | 2024 LTIP - Performance Share Units | 1745 | $0.00 | 1,745.0000 | 38,317,534 | 9999.99% | 0.00% |
| Feb. 29, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Duffy Sean W | EVP & CHIEF CLAIMS OFFICER | M | 2021 LTIP - Performance Share Units | 4835 | $0.00 | 0.0000 | 38,317,534 | 100.00% | 0.01% |
| Feb. 29, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Duffy Sean W | EVP & CHIEF CLAIMS OFFICER | M | Common Stock | 4835 | $0.00 | 11,811.0000 | 38,317,534 | 69.31% | 0.01% |
| Feb. 29, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Duffy Sean W | EVP & CHIEF CLAIMS OFFICER | F | Common Stock | 1881 | $36.47 | 9,930.0000 | 38,317,534 | 15.93% | 0.00% |
| Jan. 1, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Duffy Sean W | EVP & CHIEF CLAIMS OFFICER | F | Common Stock | 2117 | $33.88 | 6,976.0000 | 38,317,534 | 23.28% | 0.01% |
| Jan. 1, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Duffy Sean W | EVP & CHIEF CLAIMS OFFICER | M | Restricted Stock Unit | 4788 | $0.00 | 0.0000 | 38,317,534 | 100.00% | 0.01% |
| Jan. 1, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Duffy Sean W | EVP & CHIEF CLAIMS OFFICER | M | Common Stock | 4788 | $0.00 | 9,093.0000 | 38,317,534 | 111.22% | 0.01% |