Skyward Specialty Insurance Group, Inc. (SKWD) has 20 known insider and institutional holders on record. The largest holder is Westaim HIIG Limited Partnership with 7,392,237 shares. Other notable holders include WESTAIM Corp and Robinson Andrew S.
Over the last 12 months, insiders have made 58 transactions in SKWD stock — 19 buys (valued at $899.43K) and 7 sells (valued at $5.37M). Insider buying has outpaced selling during this period, which may signal confidence in the company's prospects.
SKWD Insider Ownership
Top Holder
Westaim HIIG Limited Partnership
7,392,237 shares
Buys (12 mo)
19
$899.43K value
Sells (12 mo)
7
$5.37M value
12-Month Transaction Activity
Top Insider Holders
| # |
Name |
Role |
Shares Owned |
Last Filed |
Relative Size |
| 1 |
Westaim Hiig Limited Partnership |
10 Percent Owner |
7,392,237 |
2023-07-21 |
|
| 2 |
Westaim Corp |
10 Percent Owner |
1,919,639 |
2024-05-13 |
|
| 3 |
Robinson Andrew S |
Chairman & CEO, Skyward Group |
145,574 |
2026-02-27 |
|
| 4 |
Haushill Mark W |
EVP & CFO, Skyward Group |
136,412 |
2026-02-27 |
|
| 5 |
Slaughter James Richard |
Officer, Other: Cuo - Apollo |
108,154 |
2026-02-27 |
|
| 6 |
Burkhart John A Iii |
President, Us P&c |
34,817 |
2026-02-27 |
|
| 7 |
Bodnar Dan Pk |
Chief Information Officer |
26,465 |
2026-02-27 |
|
| 8 |
Ibeson David Christopher Ben |
Officer, Other: CEO - Apollo |
21,630 |
2026-02-27 |
|
| 9 |
Shaunty Leslie |
General Counsel & Secretary |
20,751 |
2025-01-06 |
|
| 10 |
Duffy Sean W |
EVP & Chief Claims Officer |
17,963 |
2026-02-27 |
|
| 11 |
Kapadia Sandip A |
Head of Actuarial |
17,041 |
2026-02-27 |
|
| 12 |
Schmitt Thomas N |
CPO, Skyward Group |
16,523 |
2026-02-27 |
|
| 13 |
Kuczinski Anthony J |
Director |
8,903 |
2026-03-04 |
|
| 14 |
Hill Kirby |
Chairman, Captives & Programs |
8,249 |
2025-05-15 |
|
| 15 |
Peirce Christopher Locke |
Director |
3,200 |
2026-03-03 |
|
| 16 |
Dall Marcia A |
Director |
1,797 |
2025-05-09 |
|
| 17 |
Morrissey Michael J. |
Director |
1,797 |
2025-05-09 |
|
| 18 |
Creager Robert E. |
Director |
1,797 |
2025-05-09 |
|
| 19 |
Terry Katharine |
Director |
1,797 |
2025-05-09 |
|
| 20 |
Hays James Charles |
Director |
1,797 |
2025-05-09 |
|
Recent Transactions (last 12 months)
| Date |
Name |
Role |
Type |
Shares |
Price |
Value |
| 2026-03-03 |
Kuczinski Anthony J |
Director |
Informative Buy |
1,000 |
$48.13 |
$48.13K |
| 2026-03-02 |
Kuczinski Anthony J |
Director |
Informative Buy |
2,000 |
$48.79 |
$97.58K |
| 2026-02-27 |
Kuczinski Anthony J |
Director |
Informative Buy |
2,000 |
$46.88 |
$93.75K |
| 2026-03-02 |
Peirce Christopher Locke |
Director |
Informative Buy |
3,200 |
$47.30 |
$151.36K |
| 2026-02-27 |
Mcharg Taryn Leonie |
Officer, Other: CFO - Apollo |
Informative Buy |
100 |
$46.71 |
$4.67K |
| 2026-02-25 |
Mcharg Taryn Leonie |
Officer, Other: CFO - Apollo |
RSU Award |
37,854 |
- |
- |
| 2026-02-25 |
Slaughter James Richard |
Officer, Other: Cuo - Apollo |
RSU Award |
108,154 |
- |
- |
| 2026-02-25 |
Ibeson David Christopher Ben |
Officer, Other: CEO - Apollo |
RSU Award |
21,630 |
- |
- |
| 2026-02-25 |
Khan Shakoor |
Corp. Dev. Officer |
RSU Award |
1,261 |
- |
- |
| 2026-02-26 |
Bodnar Dan Pk |
Chief Information Officer |
Tax Withholding of RSU |
876 |
$45.89 |
$40.2K |
| 2026-02-25 |
Bodnar Dan Pk |
Chief Information Officer |
Option Exercise (Sell) |
2,020 |
- |
- |
| 2026-02-26 |
Schmitt Thomas N |
CPO, Skyward Group |
Tax Withholding of RSU |
1,153 |
$45.89 |
$52.91K |
| 2026-02-25 |
Schmitt Thomas N |
CPO, Skyward Group |
Option Exercise (Sell) |
2,525 |
- |
- |
| 2026-02-26 |
Kapadia Sandip A |
Head of Actuarial |
Tax Withholding of RSU |
847 |
$45.89 |
$38.87K |
| 2026-02-25 |
Kapadia Sandip A |
Head of Actuarial |
Option Exercise (Sell) |
2,020 |
- |
- |
| 2026-02-26 |
Burkhart John A Iii |
President, Us P&c |
Tax Withholding of RSU |
1,652 |
$45.89 |
$75.81K |
| 2026-02-25 |
Burkhart John A Iii |
President, Us P&c |
Option Exercise (Sell) |
3,619 |
- |
- |
| 2026-02-26 |
Duffy Sean W |
EVP & Chief Claims Officer |
Tax Withholding of RSU |
1,391 |
$45.89 |
$63.83K |
| 2026-02-25 |
Duffy Sean W |
EVP & Chief Claims Officer |
Option Exercise (Sell) |
2,861 |
- |
- |
| 2026-02-25 |
Ryan Patricia A. |
Chief Legal Officer |
RSU Award |
1,442 |
- |
- |
| 2026-02-27 |
Robinson Andrew S |
Chairman & CEO, Skyward Group |
Informative Buy |
10,821 |
$46.57 |
$503.93K |
| 2026-02-26 |
Robinson Andrew S |
Chairman & CEO, Skyward Group |
Tax Withholding of RSU |
6,916 |
$45.89 |
$317.38K |
| 2026-02-25 |
Robinson Andrew S |
Chairman & CEO, Skyward Group |
Option Exercise (Sell) |
15,151 |
- |
- |
| 2026-02-26 |
Haushill Mark W |
EVP & CFO, Skyward Group |
Tax Withholding of RSU |
1,436 |
$45.89 |
$65.9K |
| 2026-02-25 |
Haushill Mark W |
EVP & CFO, Skyward Group |
Option Exercise (Sell) |
3,787 |
- |
- |
