A Form 4 is filed within two business days of a company insider — an officer, a director, or a holder of more than ten percent of the stock — changing their position in the shares. All 12 filings in this group are Form 4s for Skyward Specialty Insurance Group, Inc.
The difficulty with reading these filings as a group is that a single form type covers transactions that mean entirely different things. An executive spending their own money to buy stock and an executive having shares withheld to pay tax on a vesting grant both appear as a Form 4. Every filing below is therefore tagged with the nature of the underlying transaction, taken from the transaction code reported on the form itself.
Across the 12 insider filings shown, the breakdown is 7 option exercise, 2 compensation award, 2 open-market sale and 1 open-market purchase. 3 of them involved a discretionary open-market trade; the rest are compensation and administrative mechanics.
Form 4
Compensation award
Tax / Compensation Filing
2026-08-07
SKWD insider Form 4 filed for equity award, exercise, or tax withholding
HEARN PETER C (Director) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
Shares were granted as compensation rather than purchased. No cash changed hands, so the filing reflects a pay decision by the company, not a judgement about the price.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
A |
Compensation award
derivative · 2026 RSU Award
|
1,845 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: HEARN PETER C (Director)
Form 4
Open-market sale
Insider Selling
2026-06-15
SKWD insider Schmitt Thomas N (CPO, Skyward Group) sold 8,397 shares (~$431.0K)
Schmitt Thomas N, listed as CPO, Skyward Group at Skyward Specialty Insurance Group, Inc., reported an open-market sale of 8,397 SKWD shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.
The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
S |
Open-market sale
|
8,397 |
$51.32 |
$431.0K |
Filing: Form 4 (Insider Transaction)
Insider: Schmitt Thomas N (CPO, Skyward Group)
Shares: 8,397
Est. Value: $431.0K
Form 4
Open-market purchase
Insider Buying
2026-05-21
SKWD insider Kuczinski Anthony J (Director) bought 2,000 shares (~$94.2K)
Kuczinski Anthony J, listed as Director at Skyward Specialty Insurance Group, Inc., reported an open-market purchase of 2,000 SKWD shares in a Form 4 filing. Insider buying is often treated as a bullish signal because company insiders are committing their own capital.
The insider bought shares on the open market with their own money. This is the only Form 4 category that requires a discretionary cash outlay at the prevailing price.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
P |
Open-market purchase
|
200 |
$47.00 |
$9.4K |
P |
Open-market purchase
|
800 |
$47.00 |
$37.6K |
P |
Open-market purchase
|
1,000 |
$47.20 |
$47.2K |
Filing: Form 4 (Insider Transaction)
Insider: Kuczinski Anthony J (Director)
Shares: 2,000
Est. Value: $94.2K
Form 4
Open-market sale
Insider Selling
2026-05-12
SKWD insider Ashe Gena L (Director) sold 740 shares (~$34.3K)
Ashe Gena L, listed as Director at Skyward Specialty Insurance Group, Inc., reported an open-market sale of 740 SKWD shares in a Form 4 filing. This is a confirmed insider sale, not just a proposed sale notice.
The insider sold shares on the open market. Sales may be discretionary or executed automatically under a pre-arranged Rule 10b5-1 trading plan, and a Form 4 does not always make clear which applies.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
M |
Option exercise
|
1,797 |
— |
— |
S |
Open-market sale
|
100 |
$46.35 |
$4.6K |
S |
Open-market sale
|
140 |
$46.35 |
$6.5K |
S |
Open-market sale
|
500 |
$46.35 |
$23.2K |
M |
Option exercise
derivative · 2025 RSU Award
|
1,797 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: Ashe Gena L (Director)
Shares: 740
Est. Value: $34.3K
Form 4
Option exercise
Tax / Compensation Filing
2026-05-08
SKWD insider Form 4 filed for equity award, exercise, or tax withholding
Schmitt Thomas N (CPO, Skyward Group) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
The insider converted options into shares. The exercise price was fixed when the options were granted, so the timing usually tracks an expiry schedule.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
M |
Option exercise
|
3,358 |
— |
— |
F |
Tax withholding on vested shares
|
1,322 |
$43.68 |
$57.7K |
M |
Option exercise
derivative · 2023 LTIP - PSUs
|
2,525 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: Schmitt Thomas N (CPO, Skyward Group)
Shares: 4,680
Form 4
Option exercise
Tax / Compensation Filing
2026-05-08
SKWD insider Form 4 filed for equity award, exercise, or tax withholding
Kapadia Sandip A (Head of Actuarial) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
The insider converted options into shares. The exercise price was fixed when the options were granted, so the timing usually tracks an expiry schedule.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
M |
Option exercise
|
2,686 |
— |
— |
F |
Tax withholding on vested shares
|
1,374 |
$43.68 |
$60.0K |
M |
Option exercise
derivative · 2023 LTIP - PSUs
|
2,020 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: Kapadia Sandip A (Head of Actuarial)
Shares: 4,060
Form 4
Option exercise
Tax / Compensation Filing
2026-05-08
SKWD insider Form 4 filed for equity award, exercise, or tax withholding
Bodnar Dan PK (Chief Information Officer) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
The insider converted options into shares. The exercise price was fixed when the options were granted, so the timing usually tracks an expiry schedule.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
M |
Option exercise
|
2,686 |
— |
— |
F |
Tax withholding on vested shares
|
1,004 |
$43.68 |
$43.9K |
M |
Option exercise
derivative · 2023 LTIP - PSUs
|
2,020 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: Bodnar Dan PK (Chief Information Officer)
Shares: 3,690
Form 4
Option exercise
Tax / Compensation Filing
2026-05-08
SKWD insider Form 4 filed for equity award, exercise, or tax withholding
Burkhart John A III (President, US P&C) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
The insider converted options into shares. The exercise price was fixed when the options were granted, so the timing usually tracks an expiry schedule.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
M |
Option exercise
|
4,813 |
— |
— |
F |
Tax withholding on vested shares
|
1,894 |
$43.68 |
$82.7K |
M |
Option exercise
derivative · 2023 LTIP - PSUs
|
3,619 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: Burkhart John A III (President, US P&C)
Shares: 6,707
Form 4
Option exercise
Tax / Compensation Filing
2026-05-08
SKWD insider Form 4 filed for equity award, exercise, or tax withholding
HAUSHILL MARK W (CFO - Skyward Group) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
The insider converted options into shares. The exercise price was fixed when the options were granted, so the timing usually tracks an expiry schedule.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
M |
Option exercise
|
5,036 |
— |
— |
F |
Tax withholding on vested shares
|
1,982 |
$43.68 |
$86.6K |
M |
Option exercise
derivative · 2023 LTIP - PSUs
|
3,787 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: HAUSHILL MARK W (CFO - Skyward Group)
Shares: 7,018
Form 4
Option exercise
Tax / Compensation Filing
2026-05-08
SKWD insider Form 4 filed for equity award, exercise, or tax withholding
Robinson Andrew S (Director, Chairman & CEO, Skyward Group) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
The insider converted options into shares. The exercise price was fixed when the options were granted, so the timing usually tracks an expiry schedule.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
M |
Option exercise
|
20,150 |
— |
— |
F |
Tax withholding on vested shares
|
7,930 |
$43.68 |
$346.4K |
M |
Option exercise
derivative · 2023 LTIP - PSUs
|
15,151 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: Robinson Andrew S (Director, Chairman & CEO, Skyward Group)
Shares: 28,080
Form 4
Option exercise
Tax / Compensation Filing
2026-05-08
SKWD insider Form 4 filed for equity award, exercise, or tax withholding
Duffy Sean W (EVP & Chief Claims Officer) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
The insider converted options into shares. The exercise price was fixed when the options were granted, so the timing usually tracks an expiry schedule.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
M |
Option exercise
|
3,805 |
— |
— |
F |
Tax withholding on vested shares
|
1,671 |
$43.68 |
$73.0K |
M |
Option exercise
derivative · 2023 LTIP - PSUs
|
2,861 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: Duffy Sean W (EVP & Chief Claims Officer)
Shares: 5,476
Form 4
Compensation award
Tax / Compensation Filing
2026-05-08
SKWD insider Form 4 filed for equity award, exercise, or tax withholding
Terry Katharine (Director) filed a Form 4 covering compensation-related activity such as stock awards, option exercises, conversions, or tax withholding. These filings are usually neutral.
Shares were granted as compensation rather than purchased. No cash changed hands, so the filing reflects a pay decision by the company, not a judgement about the price.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
A |
Compensation award
derivative · 2026 RSU Award
|
3,334 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: Terry Katharine (Director)