Bowhead Specialty Holdings Inc.

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

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SCHEDULE 14A

Proxy Statement Pursuant to Section 14(a) of

the Securities Exchange Act of 1934

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☐ Preliminary Proxy Statement

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☒ Definitive Proxy Statement

☐ Definitive Additional Materials

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March 19, 2025

Dear Stockholder:

You are cordially invited to attend Bowhead Specialty Holdings Inc.’s 2025 Annual Meeting of Stockholders on Thursday, May 1, 2025, at 10:00 a.m., Eastern Time. The 2025 Annual Meeting of Stockholders will be held in a virtual format online at https://www.virtualshareholdermeeting.com/BOW2025.

The matters to be acted on at the 2025 Annual Meeting of Stockholders are described in the enclosed notice and proxy statement.

Your vote is important to us. Even if you plan on attending the 2025 Annual Meeting of Stockholders, we encourage you to vote your shares in advance to ensure that your vote will be represented at the meeting. To vote in advance of the meeting, you may vote online, as instructed in the attached proxy statement, or by completing, signing and returning the proxy card that is provided. You may revoke your proxy at any time before your shares are voted at the 2025 Annual Meeting of Stockholders. See the attached proxy statement for more detailed information.

We look forward to receiving your proxy and we appreciate your support.

Sincerely,

Stephen Sills

Chief Executive Officer

NOTICE OF ANNUAL MEETING OF STOCKHOLDERS

TO BE HELD ON THURSDAY, MAY 1, 2025

You are cordially invited to attend the Annual Meeting of Stockholders (the “Annual Meeting”) of Bowhead Specialty Holdings Inc. (“BSHI” or the “Company”) to be held on Thursday, May 1, 2025, at 10:00 a.m., Eastern Time, online at https://www.virtualshareholdermeeting.com/BOW2025.

At the Annual Meeting, stockholders will be invited to consider and vote upon the following matters:

1. Election of four Class I directors to serve for a three-year term of office expiring at the 2028 annual meeting of stockholders and until his or her successor is duly elected and qualified or until his or her earlier death, resignation, disqualification or removal;

2. Ratification of the appointment of PricewaterhouseCoopers LLP as our independent registered public accounting firm for the fiscal year ending December 31, 2025; and

3. Any other matter that properly comes before the Annual Meeting.

The foregoing items of business are more fully described in the proxy statement accompanying this Notice of Annual Meeting of Stockholders.

The board of directors has fixed the close of business on March 7, 2025 as the record date for the determination of stockholders entitled to notice of, and to vote at, the Annual Meeting and any postponement or adjournment thereof. A list of stockholders entitled to vote at the Annual Meeting will be available for examination during ordinary business hours for 10 days prior to the Annual Meeting at our principal executive office at 452 Fifth Avenue, New York, New York 10018. Your vote is very important to the Company and all proxies are being solicited by the board of directors. So, whether or not you plan on attending the Annual Meeting, we encourage you to submit your proxy as soon as possible (i) by accessing https://www.virtualshareholdermeeting.com/BOW2025 or (ii) by signing, dating and returning a proxy card or instruction form provided to you. By submitting your proxy promptly, you will save the Company the expense of further proxy solicitation. Please note that all votes cast online must be cast prior to 11:59 p.m., Eastern Time, on April 30, 2025.

By Order of the Board of Directors,

/s/ H. Matthew Crusey

H. Matthew Crusey

Secretary and General Counsel

March 19, 2025

New York, New York

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