Skyward Specialty Insurance Group, Inc. (SKWD) is a publicly traded company in the Unknown sector. Across all available filings, 20 corporate insiders have executed 76 transactions totaling $401.4M, demonstrating a bearish sentiment with -$401.3M in net insider flow. The most recent transaction on Jan 1, 2026 involved a transaction of 143,664 shares valued at $7.2M.
No significant insider buying has been recorded for SKWD in the recent period.
No significant insider selling has been recorded for SKWD in the recent period.
Based on recent SEC filings, insider sentiment for SKWD is bearish with an Insider Alignment Score of 0/100 and a net flow of -$401.3M. Insiders are reducing their positions, though this can be driven by factors unrelated to company outlook.
Insider trading at Skyward Specialty Insurance Group, Inc. (SKWD) refers to stock transactions made by corporate insiders—executives, directors, and beneficial owners holding more than 10% of the company's shares. These individuals have access to material non-public information and are required by law to report their trades to the SEC within two business days. Currently, 20 insiders are actively trading SKWD stock, having executed 76 transactions in the past 90 days. The most active insider is Corp Westaim (Executive), who has made 2 transactions totaling $294.5M.
Get notified when executives and directors at SKWD file new Form 4 transactions
Date | Insider | Title | Type | Shares | Price | Value | Flags |
|---|---|---|---|---|---|---|---|
| Jan 1, 2026 | Charles Hays James | Executive | Award | 143,664 | $50.00 | $7.2M | Large |
| Jan 1, 2026 | Leonie Mcharg Taryn | CFO - Apollo | Award | 7,764 | $50.00 | $388.2K | C-Suite |
| Dec 18, 2025 | A. Kapadia Sandip | Executive | Sale | 5,030 | $50.01 | $251.6K | |
| Dec 12, 2025 | A. Kapadia Sandip | Executive | Sale | 1,200 | $50.01 | $60.0K | |
| Dec 12, 2025 | A. Kapadia Sandip | Executive | Sale | 1,486 | $50.03 | $74.3K | |
| Dec 11, 2025 | N. Schmitt Thomas | Executive | Sale | 88 | $47.61 | $4.2K | |
| Aug 9, 2024 | Terry Katharine | Executive | Sale | 1,653 | $36.87 | $60.9K | |
| May 10, 2024 | S. Robinson Andrew | Executive | Sale | 23,533 | $37.21 | $875.7K | Large |
| May 10, 2024 | W. Haushill Mark | Executive | Sale | 3,244 | $37.18 | $120.6K | |
| May 10, 2024 | Hill Kirby | Executive | Sale | 8,500 | $37.02 | $314.7K | |
| May 9, 2024 | S. Robinson Andrew | Executive | Option Exercise | 59,804 | $N/A | $0 | |
| May 9, 2024 | W. Haushill Mark | Executive | Option Exercise | 9,442 | $N/A | $0 | |
| May 9, 2024 | Westaim Corp | Executive | Sale | 5,060,000 | $36.50 | $184.7M | Large |
| Mar 12, 2024 | S. Robinson Andrew | Executive | Sale | 14,243 | $35.93 | $511.8K | Large10b5-1 |
| Mar 11, 2024 | S. Robinson Andrew | Executive | Sale | 13,407 | $35.63 | $477.7K | 10b5-1 |
| TYPE | COUNT | VALUE | % |
|---|---|---|---|
Sale(S) | 24 | $401.4M | 97.8% |
Award(A) | 11 | $7.6M | 1.8% |
Payment(F) | 11 | $1.2M | 0.3% |
Purchase(P) | 2 | $39.5K | 0.0% |
Exercise(M) | 18 | $0 | 0.0% |
Other(J) | 2 | $0 | 0.0% |
Conversion(C) | 8 | $0 | 0.0% |
Insider selling pressure at Skyward Specialty Insurance Group, Inc. has increased, with 20 insiders executing 76 transactions across all time. Total sales of $401.4M significantly outpace purchases of $39.5K, resulting in a net outflow of $401.3M. This selling activity appears largely discretionary, which may warrant closer attention from investors.