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 Bowhead Specialty Holdings 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 compensation award, 4 tax withholding and 1 gift. None of the classified filings involved a discretionary open-market trade, so this period says nothing about what insiders think of the price.
Form 4
Tax withholding
Tax / Compensation Filing
2026-05-27
BOW insider Form 4 filed for equity award, exercise, or tax withholding
Yap Shirley Shek Li (Chief Accounting Officer) 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 withheld by the company to settle tax due when equity vested. This is an automatic administrative step and not a decision to sell.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
F |
Tax withholding on vested shares
|
2,353 |
$28.30 |
$66.6K |
Filing: Form 4 (Insider Transaction)
Insider: Yap Shirley Shek Li (Chief Accounting Officer)
Shares: 2,353
Form 4
Tax withholding
Tax / Compensation Filing
2026-05-26
BOW insider Form 4 filed for equity award, exercise, or tax withholding
Mulcahey Brad (CFO and Treasurer) 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 withheld by the company to settle tax due when equity vested. This is an automatic administrative step and not a decision to sell.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
F |
Tax withholding on vested shares
|
3,506 |
$28.30 |
$99.2K |
Filing: Form 4 (Insider Transaction)
Insider: Mulcahey Brad (CFO and Treasurer)
Shares: 3,506
Form 4
Tax withholding
Tax / Compensation Filing
2026-05-26
BOW insider Form 4 filed for equity award, exercise, or tax withholding
Newman David John (Chief Underwriting Officer) 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 withheld by the company to settle tax due when equity vested. This is an automatic administrative step and not a decision to sell.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
F |
Tax withholding on vested shares
|
4,506 |
$28.30 |
$127.5K |
Filing: Form 4 (Insider Transaction)
Insider: Newman David John (Chief Underwriting Officer)
Shares: 4,506
Form 4
Tax withholding
Tax / Compensation Filing
2026-05-26
BOW insider Form 4 filed for equity award, exercise, or tax withholding
Sills Stephen Jay (Director, CEO and President) 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 withheld by the company to settle tax due when equity vested. This is an automatic administrative step and not a decision to sell.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
F |
Tax withholding on vested shares
|
24,353 |
$28.46 |
$693.1K |
Filing: Form 4 (Insider Transaction)
Insider: Sills Stephen Jay (Director, CEO and President)
Shares: 24,353
Form 4
Compensation award
Tax / Compensation Filing
2026-05-04
BOW insider Form 4 filed for equity award, exercise, or tax withholding
Baker Tom (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
|
3,361 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: Baker Tom (Director)
Shares: 3,361
Form 4
Compensation award
Tax / Compensation Filing
2026-05-04
BOW insider Form 4 filed for equity award, exercise, or tax withholding
Brock-Kyle Angela (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
|
6,722 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: Brock-Kyle Angela (Director)
Shares: 6,722
Form 4
Compensation award
Tax / Compensation Filing
2026-05-04
BOW insider Form 4 filed for equity award, exercise, or tax withholding
FOY DAVID THOMAS (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
|
3,361 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: FOY DAVID THOMAS (Director)
Shares: 3,361
Form 4
Compensation award
Tax / Compensation Filing
2026-05-04
BOW insider Form 4 filed for equity award, exercise, or tax withholding
Fondriest Fabian (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
|
6,722 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: Fondriest Fabian (Director)
Shares: 6,722
Form 4
Compensation award
Tax / Compensation Filing
2026-05-04
BOW insider Form 4 filed for equity award, exercise, or tax withholding
Holman David Clifford (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
|
3,361 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: Holman David Clifford (Director)
Shares: 3,361
Form 4
Compensation award
Tax / Compensation Filing
2026-05-04
BOW insider Form 4 filed for equity award, exercise, or tax withholding
Lowenstein Price (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
|
3,361 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: Lowenstein Price (Director)
Shares: 3,361
Form 4
Compensation award
Tax / Compensation Filing
2026-05-04
BOW insider Form 4 filed for equity award, exercise, or tax withholding
Schnidman Ava (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
|
3,361 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: Schnidman Ava (Director)
Shares: 3,361
Form 4
Gift
Tax / Compensation Filing
2026-03-13
BOW insider Form 4 filed for equity award, exercise, or tax withholding
Sills Stephen Jay (Director, CEO and President) 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 transferred as a gift, typically for estate or charitable planning. No sale into the market took place.
Transactions reported on this filing
| Code |
Nature |
Shares |
Price |
Value |
G |
Gift
|
7,700 |
— |
— |
G |
Gift
|
1,540 |
— |
— |
G |
Gift
|
1,540 |
— |
— |
G |
Gift
|
1,540 |
— |
— |
G |
Gift
|
1,540 |
— |
— |
G |
Gift
|
1,540 |
— |
— |
G |
Gift
|
120,000 |
— |
— |
G |
Gift
|
120,000 |
— |
— |
Filing: Form 4 (Insider Transaction)
Insider: Sills Stephen Jay (Director, CEO and President)
Shares: 255,400