Andrew S. Robinson, Chairman and CEO of Skyward Group, made two open market purchases of Skyward Specialty Insurance Group ($SKWD) shares in the last year, totaling $1.03 million, with the most recent on February 27, 2026. This ranks 479th among 4,983 insiders, below the average of $1.46 million across 3.29 trades. He also sold shares three times for $3.09 million, most recently on June 6, 2025, ranking 2,662nd out of 11,678 insiders versus the $8.59 million average over 6.37 trades.
| 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 | Robinson Andrew S | Chairman & CEO, Skyward Group | A | 2026 LTIP - PSUs | 28841 | $0.00 | 28,841.0000 | 41,868,449 | 9999.99% | 0.07% |
| Feb. 27, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | Chairman & CEO, Skyward Group | P | Common Stock | 10821 | $46.57 | 156,395.0000 | 41,868,449 | 7.43% | 0.03% |
| Feb. 27, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | Chairman & CEO, Skyward Group | P | Common Stock | 11279 | $46.94 | 167,674.0000 | 41,868,449 | 7.21% | 0.03% |
| Feb. 25, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | Chairman & CEO, Skyward Group | M | Common Stock | 17575 | $0.00 | 152,490.0000 | 41,868,449 | 13.03% | 0.04% |
| Feb. 26, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | Chairman & CEO, Skyward Group | F | Common Stock | 6916 | $45.89 | 145,574.0000 | 41,868,449 | 4.54% | 0.02% |
| Feb. 25, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | Chairman & CEO, Skyward Group | M | 2023 LTIP - PSUs | 15151 | $0.00 | 0.0000 | 41,868,449 | 100.00% | 0.04% |
| Feb. 25, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | Chairman & CEO, Skyward Group | A | 2026 LTIP - RSUs | 28841 | $0.00 | 28,841.0000 | 41,868,449 | 9999.99% | 0.07% |
| Feb. 25, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | Chairman & CEO, Skyward Group | A | 2026 LTIP - PSUs | 28841 | $0.00 | 28,841.0000 | 41,868,449 | 9999.99% | 0.07% |
| Jan. 12, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | Chairman & CEO, Skyward Group | M | Common Stock | 50000 | $0.00 | 124,447.0000 | 41,868,449 | 67.16% | 0.12% |
| Jan. 12, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | Chairman & CEO, Skyward Group | M | 2023 IPO RSU Grant (3-Year) | 50000 | $0.00 | 0.0000 | 41,868,449 | 100.00% | 0.12% |
| Jan. 12, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | Chairman & CEO, Skyward Group | M | 2023 IPO RSU Grant (4-Year) | 50000 | $0.00 | 50,000.0000 | 41,868,449 | 50.00% | 0.12% |
| Jan. 12, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | Chairman & CEO, Skyward Group | F | Common Stock | 19675 | $46.10 | 134,915.0000 | 41,868,449 | 12.73% | 0.05% |
| Jan. 12, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | Chairman & CEO, Skyward Group | M | Common Stock | 50000 | $0.00 | 154,590.0000 | 41,868,449 | 47.81% | 0.12% |
| Jan. 12, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | Chairman & CEO, Skyward Group | F | Common Stock | 19857 | $46.10 | 104,590.0000 | 41,868,449 | 15.96% | 0.05% |
| Jan. 1, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | Chairman & CEO, Skyward Group | M | Common Stock | 15151 | $0.00 | 80,420.0000 | 41,868,449 | 23.21% | 0.04% |
| Jan. 1, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | Chairman & CEO, Skyward Group | F | Common Stock | 5973 | $51.11 | 74,447.0000 | 41,868,449 | 7.43% | 0.01% |
| Jan. 1, 2026 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | Chairman & CEO, Skyward Group | M | 2023 LTIP - RSUs | 15151 | $0.00 | 0.0000 | 41,868,449 | 100.00% | 0.04% |
| June 6, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | S | Common Stock | 36103 | $62.65 | 65,437.0000 | 41,377,460 | 35.56% | 0.09% |
| June 6, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | S | Common Stock | 168 | $63.58 | 65,269.0000 | 41,377,460 | 0.26% | 0.00% |
| May 8, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | S | Common Stock | 13786 | $59.23 | 101,540.0000 | 41,377,460 | 11.95% | 0.03% |
| May 7, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | M | 2022 LTIP - PSUs | 22796 | $0.00 | 0.0000 | 41,377,460 | 100.00% | 0.06% |
| May 7, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | M | Common Stock | 33282 | $0.00 | 115,326.0000 | 41,377,460 | 40.57% | 0.08% |
| March 6, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | S | Common Stock | 20311 | $50.24 | 82,044.0000 | 41,377,460 | 19.84% | 0.05% |
| March 6, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | M | Common Stock | 50000 | $0.00 | 102,355.0000 | 41,377,460 | 95.50% | 0.12% |
| March 6, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | M | 2023 IPO RSU Grant (3-Year) | 50000 | $0.00 | 50,000.0000 | 41,377,460 | 50.00% | 0.12% |
| Feb. 25, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | A | 2025 LTIP - PSUs | 10133 | $0.00 | 10,133.0000 | 41,377,460 | 9999.99% | 0.02% |
| Feb. 25, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | A | 2025 LTIP - RSUs | 10133 | $0.00 | 10,133.0000 | 41,377,460 | 9999.99% | 0.02% |
| Feb. 25, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | A | 2025 LTIP - PSUs | 10133 | $0.00 | 10,133.0000 | 41,377,460 | 9999.99% | 0.02% |
| Jan. 7, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | S | Common Stock | 1414 | $45.13 | 53,911.0000 | 41,377,460 | 2.56% | 0.00% |
| Jan. 7, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | S | Common Stock | 3766 | $45.07 | 59,863.0000 | 41,377,460 | 5.92% | 0.01% |
| Jan. 7, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | S | Common Stock | 4538 | $45.47 | 55,325.0000 | 41,377,460 | 7.58% | 0.01% |
| Jan. 7, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | S | Common Stock | 1294 | $45.51 | 52,617.0000 | 41,377,460 | 2.40% | 0.00% |
| Jan. 8, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | S | Common Stock | 262 | $45.53 | 52,355.0000 | 41,377,460 | 0.50% | 0.00% |
| Jan. 6, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | S | Common Stock | 130 | $47.11 | 63,676.0000 | 41,377,460 | 0.20% | 0.00% |
| Jan. 2, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | S | Common Stock | 6010 | $49.37 | 77,144.0000 | 41,377,460 | 7.23% | 0.01% |
| Jan. 3, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | S | Common Stock | 9643 | $47.83 | 67,501.0000 | 41,377,460 | 12.50% | 0.02% |
| Jan. 6, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | S | Common Stock | 47 | $47.10 | 63,629.0000 | 41,377,460 | 0.07% | 0.00% |
| Jan. 3, 2025 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | S | Common Stock | 3695 | $47.63 | 63,806.0000 | 41,377,460 | 5.47% | 0.01% |
| May 10, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | S | Common Stock | 23533 | $37.21 | 83,154.0000 | 38,317,534 | 22.06% | 0.06% |
| May 9, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | M | 2021 LTIP - Performance Share Units | 59804 | $0.00 | 0.0000 | 38,317,534 | 100.00% | 0.16% |
| May 9, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | M | Common Stock | 59804 | $0.00 | 106,687.0000 | 38,317,534 | 127.56% | 0.16% |
| March 12, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | S | Common Stock | 14243 | $35.93 | 46,883.0000 | 38,317,534 | 23.30% | 0.04% |
| March 11, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | S | Common Stock | 13407 | $35.63 | 61,126.0000 | 38,317,534 | 17.99% | 0.03% |
| March 6, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | S | Common Stock | 13374 | $35.70 | 96,883.0000 | 38,317,534 | 12.13% | 0.03% |
| March 8, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | S | Common Stock | 12109 | $35.56 | 74,533.0000 | 38,317,534 | 13.98% | 0.03% |
| March 7, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | S | Common Stock | 10241 | $35.44 | 86,642.0000 | 38,317,534 | 10.57% | 0.03% |
| March 4, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | S | Common Stock | 17246 | $36.15 | 137,696.0000 | 38,317,534 | 11.13% | 0.05% |
| March 1, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | S | Common Stock | 18689 | $36.08 | 154,942.0000 | 38,317,534 | 10.76% | 0.05% |
| March 5, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | S | Common Stock | 27439 | $35.32 | 110,257.0000 | 38,317,534 | 19.93% | 0.07% |
| Feb. 27, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | A | 2024 LTIP - Performance Share Units | 14959 | $0.00 | 14,959.0000 | 38,317,534 | 9999.99% | 0.04% |
| Feb. 27, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CHAIRMAN & CEO | A | 2024 LTIP - Common Stock | 14959 | $0.00 | 14,959.0000 | 38,317,534 | 9999.99% | 0.04% |
| Jan. 1, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CEO & PRESIDENT | M | Restricted Stock Unit | 40137 | $0.00 | 0.0000 | 38,317,534 | 100.00% | 0.10% |
| Jan. 1, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CEO & PRESIDENT | F | Common Stock | 16050 | $33.88 | 173,631.0000 | 38,317,534 | 8.46% | 0.04% |
| Jan. 1, 2024 | Skyward Specialty Insurance Group, Inc. | $SKWD | Robinson Andrew S | CEO & PRESIDENT | M | Common Stock | 40137 | $0.00 | 189,681.0000 | 38,317,534 | 26.84% | 0.10% |