STOCK TITAN
  1. Home
  2. Sec-filings
  3. BOW
  4. [Form 4] Bowhead Specialty Holdings Inc. Insider Trading Activity

Bowhead (BOW) CEO surrenders 24,353 shares to cover RSU tax

Filing Impact
(Very High)
Filing Sentiment
(Neutral)
Form Type
4

Rhea-AI Filing Summary

Bowhead Specialty Holdings Inc. CEO and President Stephen Jay Sills reported a routine tax-withholding event related to equity compensation. He surrendered 24,353 shares of common stock at $28.46 per share to cover required tax withholdings upon vesting of restricted stock units, leaving 838,926 shares held directly plus additional indirect holdings through various trusts and an LLC.

Positive

  • None.

Negative

  • None.
Insider Sills Stephen Jay
Role CEO and President
Type Security Shares Price Value
Tax Withholding Common Stock 24,353 $28.46 $693K
holding Common Stock -- -- --
holding Common Stock -- -- --
holding Common Stock -- -- --
holding Common Stock -- -- --
holding Common Stock -- -- --
holding Common Stock -- -- --
holding Common Stock -- -- --
holding Common Stock -- -- --
holding Common Stock -- -- --
holding Common Stock -- -- --
holding Common Stock -- -- --
Holdings After Transaction: Common Stock — 838,926 shares (Direct, null); Common Stock — 2,681 shares (Indirect, By Sills Family Trust 1)
Footnotes (1)
  1. Represents shares surrendered to the Issuer by the Reporting Person to pay required tax withholdings due upon vesting of restricted stock units. Includes 31,129 shares of common stock transferred on May 15, 2026, for no consideration, from the Stephen J. Sills 2024 I GRAT #2 to the direct holdings of the Reporting Person. Such transaction was exempt from reporting pursuant to Rule 16a-13 of the Securities Exchange Act of 1934, as amended.
Shares surrendered for tax 24,353 shares Tax-withholding disposition on restricted stock unit vesting
Tax-withholding share price $28.46 per share Value applied to surrendered common shares
Direct shares after event 838,926 shares Direct Bowhead common stock held following disposition
Sills 2024 LLC indirect holding 214,469 shares Bowhead common stock held indirectly via Sills 2024 LLC
Family GST Exempt Trust holding 72,000 shares Indirect holding by Stephen J. Sills Irrevocable Family GST Exempt Trust
GRAT #2 indirect holding 41,371 shares Indirect holding by Stephen J. Sills 2024 I GRAT #2
restricted stock units financial
"tax withholdings due upon vesting of restricted stock units."
Restricted stock units are a type of company reward where employees are promised shares of stock, but they only fully own these shares after meeting certain conditions, like staying with the company for a set time. They matter because they can become valuable assets and are often used to motivate employees to help the company succeed.
Rule 16a-13 regulatory
"Such transaction was exempt from reporting pursuant to Rule 16a-13 of the Securities Exchange Act"
GRAT financial
"Includes 31,129 shares of common stock transferred on May 15, 2026, from the Stephen J. Sills 2024 I GRAT #2"
GST Exempt Trust financial
"By Stephen J. Sills Irrevocable Family GST Exempt Trust"
Form 4 Insider Transactions: What Each Field Means →
SEC Form 4
FORM 4UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940
OMB APPROVAL
OMB Number:3235-0287
Estimated average burden
hours per response:0.5
Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).
Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.
1. Name and Address of Reporting Person*
Sills Stephen Jay
(Last)(First)(Middle)
C/O BOWHEAD SPECIALTY HOLDINGS INC.
452 FIFTH AVENUE
(Street)
NEW YORK NEW YORK 10018
(City)(State)(Zip)
UNITED STATES
(Country)		2. Issuer Name and Ticker or Trading Symbol
Bowhead Specialty Holdings Inc. [ BOW ] 		5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)
XDirector10% Owner
XOfficer (give title below)Other (specify below)
CEO and President
2a. Foreign Trading Symbol
3. Date of Earliest Transaction (Month/Day/Year)
05/22/2026		6. Individual or Joint/Group Filing (Check Applicable Line)
XForm filed by One Reporting Person
Form filed by More than One Reporting Person
4. If Amendment, Date of Original Filed (Month/Day/Year)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3) 2. Transaction Date (Month/Day/Year)2A. Deemed Execution Date, if any (Month/Day/Year)3. Transaction Code (Instr. 8) 4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5) 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4)
CodeVAmount(A) or (D)Price
Common Stock05/22/2026F24,353(1)D$28.46838,926(2)D
Common Stock2,681IBy Sills Family Trust 1
Common Stock2,681IBy Sills Family Trust 2
Common Stock2,681IBy Sills Family Trust 3
Common Stock2,681IBy Sills Family Trust 4
Common Stock2,681IBy Sills Family Trust 5
Common Stock120,000IStephen J. Sills 2024 I GRAT #5
Common Stock75,000IBy Stephen J. Sills 2024 I GRAT #4
Common Stock97,911IBy Stephen J. Sills 2024 I GRAT #3
Common Stock72,000IBy Stephen J. Sills Irrevocable Family GST Exempt Trust
Common Stock214,469IBy Sills 2024 LLC
Common Stock41,371(2)IBy Stephen J. Sills 2024 I GRAT #2
Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned
(e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3) 2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (Month/Day/Year)3A. Deemed Execution Date, if any (Month/Day/Year)4. Transaction Code (Instr. 8) 5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) 6. Date Exercisable and Expiration Date (Month/Day/Year)7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4) 8. Price of Derivative Security (Instr. 5) 9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4)
CodeV(A)(D)Date ExercisableExpiration DateTitleAmount or Number of Shares
Explanation of Responses:
1. Represents shares surrendered to the Issuer by the Reporting Person to pay required tax withholdings due upon vesting of restricted stock units.
2. Includes 31,129 shares of common stock transferred on May 15, 2026, for no consideration, from the Stephen J. Sills 2024 I GRAT #2 to the direct holdings of the Reporting Person. Such transaction was exempt from reporting pursuant to Rule 16a-13 of the Securities Exchange Act of 1934, as amended.
Remarks:
/s/ H. Matthew Crusey, as attorney-in-fact05/26/2026
** Signature of Reporting PersonDate
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.
* Form 4: SEC 1474 (03-26)

Source: View Original Filing on SEC EDGAR

FAQ

What did Bowhead (BOW) CEO Stephen Jay Sills report in this Form 4?

Stephen Jay Sills reported a routine share disposition to cover taxes on vesting restricted stock units. He surrendered 24,353 Bowhead common shares and continues to hold 838,926 shares directly, along with additional indirect holdings through various trusts and an LLC.

Was the Bowhead (BOW) CEO’s 24,353-share disposition an open-market sale?

No, the 24,353-share disposition was not an open-market sale. Shares were surrendered to Bowhead to pay required tax withholdings upon vesting of restricted stock units, a common administrative mechanism rather than a discretionary decision to sell shares in the market.

How many Bowhead (BOW) shares does Stephen Jay Sills hold directly after this filing?

After the tax-withholding share surrender, Stephen Jay Sills holds 838,926 Bowhead common shares directly. This figure reflects his remaining direct ownership following the 24,353 shares delivered back to the issuer to satisfy the tax obligation on vested restricted stock units.

What indirect Bowhead (BOW) holdings are associated with Stephen Jay Sills?

Indirect holdings include Bowhead shares held through entities such as Sills 2024 LLC and several trusts, including Stephen J. Sills 2024 I GRATs and a family GST Exempt Trust. Each entry lists the number of common shares held by that specific trust or entity.

What price per share was used for the Bowhead (BOW) tax-withholding shares?

The surrendered shares used to cover tax withholdings were valued at $28.46 per Bowhead common share. This price applies to the 24,353 shares delivered to the issuer in connection with required tax payments on the vesting restricted stock units reported in the Form 4.