There have been 50 recent insider transactions recorded for Skyward Specialty Insurance Group, Inc. (SKWD), including 11 buys and 37 sells. Total insider buying was valued at $899.43K and total insider selling at $6.03M.
Notable insiders with recent activity include Kuczinski Anthony J, Peirce Christopher Locke, Robinson Andrew S. Insider transactions can provide insights into how company leadership views the stock's valuation and future prospects.
Insider Transactions — SKWD
| Date |
Name |
Role |
Transaction |
Shares |
Avg. Price |
Value |
Shares Owned |
| 2026-03-03 |
Kuczinski Anthony J |
Director |
Informative Buy |
1,000 |
$48.13 |
$48.13K |
11,903 |
| 2026-03-02 |
Peirce Christopher Locke |
Director |
Informative Buy |
3,200 |
$47.30 |
$151.36K |
3,200 |
| 2026-03-02 |
Kuczinski Anthony J |
Director |
Informative Buy |
2,000 |
$48.79 |
$97.58K |
10,903 |
| 2026-02-27 |
Robinson Andrew S |
Chairman & CEO, Skyward Group |
Informative Buy |
10,821 |
$46.57 |
$503.93K |
156,395 |
| 2026-02-27 |
Mcharg Taryn Leonie |
Officer, Other: CFO - Apollo |
Informative Buy |
100 |
$46.71 |
$4.67K |
100 |
| 2026-02-27 |
Kuczinski Anthony J |
Director |
Informative Buy |
2,000 |
$46.88 |
$93.75K |
8,903 |
| 2026-02-26 |
Haushill Mark W |
EVP & CFO, Skyward Group |
Tax Withholding of RSU |
1,436 |
$45.89 |
$65.9K |
136,412 |
| 2026-02-26 |
Robinson Andrew S |
Chairman & CEO, Skyward Group |
Tax Withholding of RSU |
6,916 |
$45.89 |
$317.38K |
145,574 |
| 2026-02-26 |
Duffy Sean W |
EVP & Chief Claims Officer |
Tax Withholding of RSU |
1,391 |
$45.89 |
$63.83K |
17,963 |
| 2026-02-26 |
Burkhart John A Iii |
President, Us P&c |
Tax Withholding of RSU |
1,652 |
$45.89 |
$75.81K |
34,817 |
| 2026-02-26 |
Kapadia Sandip A |
Head of Actuarial |
Tax Withholding of RSU |
847 |
$45.89 |
$38.87K |
17,041 |
| 2026-02-26 |
Schmitt Thomas N |
CPO, Skyward Group |
Tax Withholding of RSU |
1,153 |
$45.89 |
$52.91K |
16,523 |
| 2026-02-26 |
Bodnar Dan Pk |
Chief Information Officer |
Tax Withholding of RSU |
876 |
$45.89 |
$40.2K |
26,465 |
| 2026-02-25 |
Haushill Mark W |
EVP & CFO, Skyward Group |
Option Exercise (Sell) |
3,787 |
- |
- |
- |
| 2026-02-25 |
Robinson Andrew S |
Chairman & CEO, Skyward Group |
Option Exercise (Sell) |
15,151 |
- |
- |
- |
| 2026-02-25 |
Ryan Patricia A. |
Chief Legal Officer |
RSU Award |
1,442 |
- |
- |
1,442 |
| 2026-02-25 |
Duffy Sean W |
EVP & Chief Claims Officer |
Option Exercise (Sell) |
2,861 |
- |
- |
- |
| 2026-02-25 |
Burkhart John A Iii |
President, Us P&c |
Option Exercise (Sell) |
3,619 |
- |
- |
- |
| 2026-02-25 |
Kapadia Sandip A |
Head of Actuarial |
Option Exercise (Sell) |
2,020 |
- |
- |
- |
| 2026-02-25 |
Schmitt Thomas N |
CPO, Skyward Group |
Option Exercise (Sell) |
2,525 |
- |
- |
- |
| 2026-02-25 |
Bodnar Dan Pk |
Chief Information Officer |
Option Exercise (Sell) |
2,020 |
- |
- |
- |
| 2026-02-25 |
Khan Shakoor |
Corp. Dev. Officer |
RSU Award |
1,261 |
- |
- |
1,261 |
| 2026-02-25 |
Ibeson David Christopher Ben |
Officer, Other: CEO - Apollo |
RSU Award |
21,630 |
- |
- |
21,630 |
| 2026-02-25 |
Slaughter James Richard |
Officer, Other: Cuo - Apollo |
RSU Award |
108,154 |
- |
- |
108,154 |
| 2026-02-25 |
Mcharg Taryn Leonie |
Officer, Other: CFO - Apollo |
RSU Award |
37,854 |
- |
- |
37,854 |
| 2026-02-09 |
Schmitt Thomas N |
CPO, Skyward Group |
Informative Sell |
2,616 |
$43.49 |
$113.77K |
14,747 |
| 2026-02-01 |
Peirce Christopher Locke |
Officer |
Unknown |
- |
- |
- |
- |
| 2026-01-12 |
Haushill Mark W |
EVP & CFO, Skyward Group |
Option Exercise (Sell) |
6,665 |
- |
- |
- |
| 2026-01-12 |
Robinson Andrew S |
Chairman & CEO, Skyward Group |
Option Exercise (Sell) |
50,000 |
- |
- |
- |
| 2026-01-12 |
Duffy Sean W |
EVP & Chief Claims Officer |
Option Exercise (Sell) |
5,000 |
- |
- |
- |
| 2026-01-12 |
Burkhart John A Iii |
President, Us P&c, Skyward Grp |
Option Exercise (Sell) |
6,665 |
- |
- |
- |
| 2026-01-12 |
Kapadia Sandip A |
Head of Actuarial |
Option Exercise (Sell) |
5,000 |
- |
- |
- |
| 2026-01-12 |
Schmitt Thomas N |
CPO, Skyward Group |
Option Exercise (Sell) |
5,000 |
- |
- |
- |
| 2026-01-12 |
Bodnar Dan Pk |
Chief Information Officer |
Option Exercise (Sell) |
5,000 |
- |
- |
- |
| 2026-01-01 |
Robinson Andrew S |
Officer |
Unknown |
- |
- |
- |
- |
| 2025-06-16 |
Haushill Mark W |
EVP & CFO |
Informative Sell |
10,566 |
$59.07 |
$624.11K |
123,063 |
| 2025-06-13 |
Haushill Mark W |
EVP & CFO |
Informative Sell |
52,748 |
$58.76 |
$3.1M |
133,629 |
| 2025-06-06 |
Robinson Andrew S |
Chairman & CEO |
Informative Sell |
168 |
$63.58 |
$10.68K |
65,269 |
| 2025-05-14 |
Hill Kirby |
Chairman, Captives & Programs |
Informative Sell |
8,249 |
$60.87 |
$502.13K |
8,249 |
| 2025-05-09 |
Morrissey Michael J. |
Director |
Option Exercise (Sell) |
2,779 |
- |
- |
- |
| 2025-05-09 |
Dall Marcia A |
Director |
Option Exercise (Sell) |
2,779 |
- |
- |
- |
| 2025-05-09 |
Creager Robert E. |
Director |
Option Exercise (Sell) |
2,779 |
- |
- |
- |
| 2025-05-09 |
Ashe Gena L |
Director |
Option Exercise (Sell) |
2,779 |
- |
- |
- |
| 2025-05-09 |
Hays James Charles |
Director |
Option Exercise (Sell) |
2,779 |
- |
- |
- |
| 2025-05-09 |
Terry Katharine |
Director |
Option Exercise (Sell) |
2,779 |
- |
- |
- |
| 2025-05-09 |
Kuczinski Anthony J |
Director |
Option Exercise (Sell) |
2,779 |
- |
- |
- |
| 2025-05-08 |
Haushill Mark W |
EVP & CFO |
Informative Sell |
3,447 |
$59.23 |
$204.17K |
186,146 |
| 2025-05-08 |
Robinson Andrew S |
Chairman & CEO |
Informative Sell |
13,786 |
$59.23 |
$816.57K |
101,540 |
| 2025-05-07 |
Haushill Mark W |
EVP & CFO |
Option Exercise (Sell) |
5,699 |
- |
- |
- |
| 2025-05-07 |
Robinson Andrew S |
Chairman & CEO |
Option Exercise (Sell) |
22,796 |
- |
- |
- |
■ Informative Buy/Sell — open market transaction (most significant)
■ Uninformative Buy — award, option exercise, conversion
■ Uninformative Sell — tax withholding, award vest sale
■ Neutral — gift, trust, expiry
