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February 21, 2024
Stephen Sills
Chief Executive Officer
Bowhead Holdings Inc.
1411 Broadway, Suite 3800
New York, NY 10018
Re:Bowhead Holdings Inc.
Amendment No. 1 to Draft Registration Statement on Form S-1
Submitted February 5, 2024
CIK No. 0002002473
Dear Stephen Sills:
            We have reviewed your amended draft registration statement and have the following
comments.
            Please respond to this letter by providing the requested information and either submitting
an amended draft registration statement or publicly filing your registration statement on
EDGAR. If you do not believe a comment applies to your facts and circumstances or do not
believe an amendment is appropriate, please tell us why in your response.
            After reviewing the information you provide in response to this letter and your amended
draft registration statement or filed registration statement, we may have additional comments.
Amendment No. 1 to Draft Registration Statement on Form S-1
Prospectus Summary
Who We Are, page 1
1.We note your responses to prior comments 6 and 14, which indicate that you are still
engaged in ongoing negotiations regarding arrangements with AmFam and will provide
discussion of new contractual terms in a future filing once agreed upon. However, given
that you appear to be operating under current arrangements or terms during the historical
financial statement periods presented in the filing, we reissue these comments in part. To
the extent that your agreements with AmFam and other parties have not concluded at the
time you make a public filing, revise your disclosures to provide a more fulsome
discussion of the contractual terms and rights between you and AmFam under your
current arrangement and quantify any related financial statement impacts for each
period presented. For example, discussion should include, but not be limited to, fee terms,

 FirstName LastNameStephen Sills
 Comapany NameBowhead Holdings Inc.
 February 21, 2024 Page 2
 FirstName LastName
Stephen Sills
Bowhead Holdings Inc.
February 21, 2024
Page 2
whether any authority parameters exist, how decisions are made, details of any
termination provisions, and whether there is a right of refusal or denial by either entity.
Our Structure, page 9
2.We note your response to prior comment 10. Based on your response, revise your
disclosure to indicate the current term of your agreement with American Family prior to
any public filing of this draft registration statement. To the extent that negotiations with
American Family have not concluded by that time, revise your disclosure, including in the
risk factors to discuss the negotiations with American Family and the possible
implications if the parties cannot reach an agreement.
Summary of Risk Factors, page 10
3.We note your response to prior comment 13. Revise the bullet points in this section to
better introduce the risk factors you discuss in the main risk factors section. For instance,
the final bullet point on page 11 should identify your controlling shareholder, and the key
parties that exert influence over that shareholder.
Risk Factors
Risks Related to Our Operations
We could be adversely affected by the loss of one or more key personnel, page 30
4.We note your response to prior comment 20 and reissue. Revise this risk factor to discuss
the extent to which your key personnel, including those representing key lines of business
and your claims processing, are covered by employment or non-compete contracts. Revise
your discussion in an appropriate portion of your business or management's discussion
sections to discuss the extent to which management has a policy to enter into contractual
arrangements with key employees to minimize the risk of disruption to your business in
the event of a key employee's departure.
Risks Related to this Offering and Ownership of Our Common Stock
BIHL, an endity owned by our Pre-IPO Investors, page 42
5.We note your response to prior comment 12. Revise this risk factor, including its heading,
or add a new risk factor to discuss the fact that BIHL's main shareholders often engage in
related businesses, and are not restricted in competing with Bowhead.
Business
Competition, page 83
6.We note your response to prior comment 26. Please revise your disclosure on this page to
include the criteria you used to identify these companies as your competitors to
give potential investors a more detailed understanding of how you identified the listed
companies, or advise.

 FirstName LastNameStephen Sills
 Comapany NameBowhead Holdings Inc.
 February 21, 2024 Page 3
 FirstName LastName
Stephen Sills
Bowhead Holdings Inc.
February 21, 2024
Page 3
Regulation
IRIS Ratios, page 89
7.We note your response to prior comment 28. To the extent that you continue to have
results outside the normal range as of 2023, please tell us the specific areas that fell
outside the normal range, with particular attention to any areas that fell outside the range
for both 2022 and 2023. Supplement that response with an explanation of
how management chose to discuss Bowhead's risk exposure in its discussion of the
business financial condition in discussing its 2023 financial condition.
            Please contact Cara Lubit at 202-551-5909 or Robert Klein at 202-551-3847 if you have
questions regarding comments on the financial statements and related matters. Please contact
Aisha Adegbuyi at 202-551-8754 or Christian Windsor at 202-551-3419 with any other
questions.
Sincerely,
Division of Corporation Finance
Office of Finance
cc:       Dwight S. Yoo, Esq.