| $705M | ||
| $677M | ||
| $350M | ||
| $213M | ||
| $93M | ||
| $77M |
Buys | $1,527,715 | 7 | 54 |
Sells | $969,133 | 6 | 46 |
| Robinson Andrew S | Chairman & CEO, Skyward Group | 1 | $1.03M | 0 | $0 | $1.03M |
| Kuczinski Anthony J | director | 4 | $333,665 | 0 | $0 | $333,665 |
| Peirce Christopher Locke | director | 1 | $151,360 | 0 | $0 | $151,360 |
| McHarg Taryn Leonie | CFO - Apollo | 1 | $9,320 | 0 | $0 | $9,320 |
| Ashe Gena L | director | 0 | $0 | 1 | $34,299 | $-34,299 |
| Kapadia Sandip A | Head of Actuarial | 0 | $0 | 2 | $385,907 | $-385,907 |
| Schmitt Thomas N | CHIEF PEOPLE & ADMIN.OFFICER | 0 | $0 | 3 | $548,927 | $-548,927 |
Incorporated in 2006 and headquartered in Houston, Texas, Skyward Specialty Insurance Group, Inc. functions as an insurance holding company. The firm specializes in writing commercial property and casualty insurance policies for clients across the United States. Its extensive range of coverages includes general liability, excess liability, professional liability, commercial auto, group accident and health, property, surety, and workers' compensation.
Over the last 12 months, insiders at Skyward Specialty Insurance Group, Inc. have bought $1.53M and sold $969,133 worth of Skyward Specialty Insurance Group, Inc. stock.
On average, over the past 5 years, insiders at Skyward Specialty Insurance Group, Inc. have bought $522,422 and sold $105.63M worth of stock each year.
Highest buying activity among insiders over the last 12 months: Robinson Andrew S (Chairman & CEO, Skyward Group) — $1.03M. Kuczinski Anthony J (director) — $333,665. Peirce Christopher Locke (director) — $151,360.
The last purchase of 2,000 shares for transaction amount of $94,200 was made by Kuczinski Anthony J (director) on 2026‑05‑21.
| 2026-06-12 | Sale | Schmitt Thomas N | CPO, Skyward Group | 8,397 0.0212% | $51.32 | $430,963 | +16.60% | |
| 2026-05-21 | Kuczinski Anthony J | director | 2,000 0.0049% | $47.10 | $94,200 | +23.29% | ||
| 2026-05-11 | Sale | Ashe Gena L | director | 740 0.0017% | $46.35 | $34,299 | +25.68% | |
| 2026-03-03 | Kuczinski Anthony J | director | 1,000 0.0024% | $48.13 | $48,132 | +13.95% | ||
| 2026-03-02 | Kuczinski Anthony J | director | 2,000 0.0052% | $48.79 | $97,582 | +12.97% | ||
| 2026-03-02 | Peirce Christopher Locke | director | 3,200 0.008% | $47.30 | $151,360 | +12.97% | ||
| 2026-02-27 | Robinson Andrew S | Chairman & CEO, Skyward Group | 22,100 0.0549% | $46.76 | $1.03M | +18.05% | ||
| 2026-02-27 | Kuczinski Anthony J | director | 2,000 0.005% | $46.88 | $93,750 | +18.05% | ||
| 2026-02-27 | McHarg Taryn Leonie | CFO - Apollo | 200 0.0005% | $46.60 | $9,320 | +18.05% | ||
| 2026-02-09 | Sale | Schmitt Thomas N | CPO, Skyward Group | 2,616 0.0066% | $43.49 | $113,774 | +23.55% | |
| 2025-12-18 | Sale | Kapadia Sandip A | Head of Actuarial | 5,030 0.012% | $50.01 | $251,550 | -4.92% | |
| 2025-12-12 | Sale | Kapadia Sandip A | Head of Actuarial | 2,686 0.0067% | $50.02 | $134,357 | -0.93% | |
| 2025-12-11 | Sale | Schmitt Thomas N | CHIEF PEOPLE & ADMIN.OFFICER | 88 0.0002% | $47.61 | $4,190 | -0.53% | |
| 2025-06-16 | Sale | HAUSHILL MARK W | EVP & CFO | 10,566 0.0261% | $59.07 | $624,109 | -20.54% | |
| 2025-06-13 | Sale | HAUSHILL MARK W | EVP & CFO | 52,748 0.1309% | $58.76 | $3.1M | -19.68% | |
| 2025-06-06 | Sale | Robinson Andrew S | CHAIRMAN & CEO | 36,271 0.0901% | $62.65 | $2.27M | -24.52% | |
| 2025-05-14 | Sale | Hill Kirby | Chairman, Captives & Programs | 8,249 0.0204% | $60.87 | $502,135 | -22.07% | |
| 2025-05-08 | Sale | HAUSHILL MARK W | EVP & CFO | 3,447 0.0085% | $59.23 | $204,172 | -19.95% | |
| 2025-05-08 | Sale | Robinson Andrew S | CHAIRMAN & CEO | 13,786 0.034% | $59.23 | $816,570 | -19.95% | |
| 2025-03-17 | Sale | Duffy Sean W | EVP & CHIEF CLAIMS OFFICER | 5,625 0.0138% | $48.90 | $275,063 | -1.01% |
| Robinson Andrew S | Chairman & CEO, Skyward Group | 167674 0.3777% | $10.21M | 1 | 17 | |
| Kuczinski Anthony J | director | 15977 0.036% | $972,839.53 | 6 | 0 | +23.44% |
| Peirce Christopher Locke | director | 3200 0.0072% | $194,848.00 | 1 | 0 | |
| McHarg Taryn Leonie | CFO - Apollo | 100 0.0002% | $6,089.00 | 1 | 0 |
$5,041,374 | 677 | 7.30% | $1.46B | |
$25,923,814 | 107 | -7.96% | $1.99B | |
$15,888,532 | 99 | 36.44% | $1.06B | |
$4,309,045 | 97 | 6.81% | $2.51B | |
$9,320,810 | 93 | 7.25% | $6.13B |
| Increased Positions | 141 | +58.26% | 5M | +14.29% |
| Decreased Positions | 111 | -45.87% | 5M | -13.08% |
| New Positions | 47 | New | 2M | New |
| Sold Out Positions | 31 | Sold Out | 1M | Sold Out |
| Total Postitions | 272 | +12.4% | 38M | +1.21% |
| Blackrock, Inc. | $130,100.00 | 6.69% | 2.68M | +76,906 | +2.96% | 2025-09-30 |
| Vanguard Group Inc | $119,257.00 | 6.13% | 2.45M | +120,663 | +5.17% | 2025-09-30 |
| Capital International Investors | $107,582.00 | 5.53% | 2.21M | 0 | 0% | 2025-09-30 |
| Reinhart Partners, Llc. | $78,450.00 | 4.03% | 1.61M | +654,500 | +68.25% | 2025-09-30 |
| Invesco Ltd. | $67,163.00 | 3.45% | 1.38M | -408,738 | -22.83% | 2025-09-30 |
| Champlain Investment Partners, Llc | $66,745.00 | 3.43% | 1.37M | +224,122 | +19.51% | 2025-09-30 |
| Price T Rowe Associates Inc /Md/ | $55,925.00 | 2.88% | 1.15M | +35,529 | +3.19% | 2025-09-30 |
| State Street Corp | $54,659.00 | 2.81% | 1.12M | +28,463 | +2.6% | 2025-09-30 |
| Capital World Investors | $49,481.00 | 2.54% | 1.02M | 0 | 0% | 2025-09-30 |
| Balyasny Asset Management L.P. | $46,051.00 | 2.37% | 947,170 | +762,079 | +411.73% | 2025-09-30 |