SecProbe.io

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 Document BOWHEAD SPECIALTY HOLDINGS INC. 452 Fifth Avenue New York, New York 10018 June 16, 2025 BY EDGAR Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.E. Washington, DC 20549-3561 Attn: Aisha Adegbuyi Re:      Bowhead Specialty Holdings Inc. Registration Statement on Form S-3 File No. 333-287860 Dear Ms. Adegbuyi: Pursuant to Rule 461(a) under the Securities Act of 1933, we respectfully request that the effective date of the registrant's above-referenced Registration Statement on Form S-3 be accelerated by the Securities and Exchange Commission to 4:00 p.m. ET on June 18, 2025, or as soon as practicable thereafter, or at such other time as the registrant or its legal counsel may request by telephone to the staff of the Securities and Exchange Commission. We request that we be notified of such effectiveness by a telephone call to Dwight S. Yoo of Skadden, Arps, Slate, Meagher & Flom LLP at (212) 735-2573 and that such effectiveness also be confirmed in writing. Very truly yours, BOWHEAD SPECIALTY HOLDINGS INC. By: /s/ Brand Mulcahey Name: Brand Mulcahey Title: Chief Financial Officer cc:    Stephen Sills, Chief Executive Officer, Bowhead Specialty Holdings Inc. H. Matthew Crusey, General Counsel, Bowhead Specialty Holdings Inc. Dwight S. Yoo, Skadden, Arps, Slate, Meagher & Flom LLP Todd E. Freed, Skadden, Arps, Slate, Meagher & Flom LLP 2

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 Document BOWHEAD SPECIALTY HOLDINGS INC. 452 Fifth Avenue New York, New York 10018 June 16, 2025 BY EDGAR Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.E. Washington, DC 20549-3561 Attn: Aisha Adegbuyi Re:      Bowhead Specialty Holdings Inc. Registration Statement on Form S-3 File No. 333-287859 Dear Ms. Adegbuyi: Pursuant to Rule 461(a) under the Securities Act of 1933, we respectfully request that the effective date of the registrant's above-referenced Registration Statement on Form S-3 be accelerated by the Securities and Exchange Commission to 4:00 p.m. ET on June 18, 2025, or as soon as practicable thereafter, or at such other time as the registrant or its legal counsel may request by telephone to the staff of the Securities and Exchange Commission. We request that we be notified of such effectiveness by a telephone call to Dwight S. Yoo of Skadden, Arps, Slate, Meagher & Flom LLP at (212) 735-2573 and that such effectiveness also be confirmed in writing. Very truly yours, BOWHEAD SPECIALTY HOLDINGS INC. By: /s/ Brand Mulcahey Name: Brand Mulcahey Title: Chief Financial Officer cc:    Stephen Sills, Chief Executive Officer, Bowhead Specialty Holdings Inc. H. Matthew Crusey, General Counsel, Bowhead Specialty Holdings Inc. Dwight S. Yoo, Skadden, Arps, Slate, Meagher & Flom LLP Todd E. Freed, Skadden, Arps, Slate, Meagher & Flom LLP 2

<DOCUMENT>
<TYPE>TEXT-EXTRACT
<SEQUENCE>2
<FILENAME>filename2.txt
<TEXT>
 June 13, 2025

Stephen Sills
Chief Executive Officer
Bowhead Specialty Holdings Inc.
452 Fifth Avenue
New York, New York 10018

 Re: Bowhead Specialty Holdings Inc.
 Registration Statement on Form S-3
 Filed June 6, 2025
 File No. 333-287860
Dear Stephen Sills:

 This is to advise you that we have not reviewed and will not review your
registration
statement.

 Please refer to Rules 460 and 461 regarding requests for acceleration.
We remind you
that the company and its management are responsible for the accuracy and
adequacy of their
disclosures, notwithstanding any review, comments, action or absence of action
by the staff.

 Please contact Aisha Adegbuyi at 202-551-8754 with any questions.

 Sincerely,

 Division of
Corporation Finance
 Office of Finance
cc: Dwight S. Yoo, Esq.
</TEXT>
</DOCUMENT>

<DOCUMENT>
<TYPE>TEXT-EXTRACT
<SEQUENCE>2
<FILENAME>filename2.txt
<TEXT>
 June 13, 2025

Stephen Sills
Chief Executive Officer
Bowhead Specialty Holdings Inc.
452 Fifth Avenue
New York, New York 10018

 Re: Bowhead Specialty Holdings Inc.
 Registration Statement on Form S-3
 Filed June 6, 2025
 File No. 333-287859
Dear Stephen Sills:

 This is to advise you that we have not reviewed and will not review your
registration
statement.

 Please refer to Rules 460 and 461 regarding requests for acceleration.
We remind you
that the company and its management are responsible for the accuracy and
adequacy of their
disclosures, notwithstanding any review, comments, action or absence of action
by the staff.

 Please contact Aisha Adegbuyi at 202-551-8754 with any questions.

 Sincerely,

 Division of
Corporation Finance
 Office of Finance
cc: Dwight S. Yoo, Esq.
</TEXT>
</DOCUMENT>

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BOWHEAD SPECIALTY HOLDINGS INC.

452 Fifth Avenue

New York, New York 10018

October 21, 2024

BY EDGAR

Securities and Exchange Commission

Division of Corporation Finance

100 F Street, N.E.

Washington, DC 20549-3561

Attn: Aisha Adegbuyi

Re:

 Bowhead Specialty Holdings Inc.

 Registration Statement on Form S-1

 File No. 333-282757

Dear Ms. Adegbuyi:

Pursuant to Rule 461 under the Securities Act of 1933, we respectfully request that the effective date of the registrant's above-referenced Registration Statement on Form S-1 be accelerated by the Securities and Exchange Commission to 5:00 p.m. ET on October 23, 2024, or as soon as practicable thereafter, or at such other time as the registrant or its legal counsel may request by telephone to the staff of the Securities and Exchange Commission.

We request that we be notified of such effectiveness by a telephone call to Dwight Yoo of Skadden, Arps, Slate, Meagher & Flom LLP at (212) 735-2573 and that such effectiveness also be confirmed in writing.

Very truly yours,

BOWHEAD SPECIALTY HOLDINGS INC.

By:

 /s/ Brad Mulcahey

Name:

 Brad Mulcahey

Title:

 Chief Financial Officer

cc:

 Stephen Sills, Chief Executive Officer, Bowhead Specialty Holdings Inc.

 H. Matthew Crusey, General Counsel, Bowhead Specialty Holdings Inc.

 Dwight Yoo, Skadden, Arps, Slate, Meagher & Flom LLP

 Todd E. Freed, Skadden, Arps, Slate, Meagher & Flom LLP

 Laura Kaufman Belkhayat, Skadden, Arps, Slate, Meagher & Flom LLP

 Marc D. Jaffe, Latham & Watkins LLP

 Erika L. Weinberg, Latham & Watkins LLP

 Gary D. Boss, Latham & Watkins LLP

2

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J.P. Morgan Securities LLC

383 Madison Avenue

New York, New York 10179

Morgan Stanley & Co. LLC

1585 Broadway

New York, New York 10036

Keefe, Bruyette & Woods, Inc.

787 Seventh Avenue

New York, New York 10019

October 21, 2024

VIA EDGAR

Securities and Exchange Commission

Division of Corporation Finance

100 F Street, N.E.

Washington, D.C. 20549-3561

Attention:    Aisha Adegbuyi

Re: Bowhead Specialty Holdings Inc.

Registration Statement on Form S-1

File No. 333-282757

Acceleration Request

Requested Date: October 23, 2024

Requested Time: 5:00 P.M. Eastern Time

Dear Ms. Adegbuyi:

In accordance with Rule 461 under the Securities Act of 1933, as amended (the “Act”), we, as representatives of the several underwriters, hereby join in the request of Bowhead Specialty Holdings Inc. (the “Company”) for acceleration of the effective date of the above-referenced Registration Statement, requesting effectiveness as of 5:00 P.M., Eastern Time, on October 23, 2024, or as soon thereafter as practicable or at such later time as the Company or its outside counsel, Skadden, Arps, Slate, Meagher & Flom LLP, may request via telephone call to the staff of the Division of Corporation Finance of the Securities and Exchange Commission.

Pursuant to Rule 460 under the Act, please be advised that we, as representatives of the several underwriters, will take reasonable steps to secure adequate distribution of the preliminary prospectus, to underwriters, dealers, institutions and others, prior to the requested effective time of the Registration Statement.

We, the undersigned, as representatives of the several underwriters, have complied and will comply, and we have been informed by the participating underwriters that they have complied and will comply, with the requirements of Rule 15c2-8 under the Securities Exchange Act of 1934, as amended.

Very truly yours,

J.P. MORGAN SECURITIES LLC

By: /s/ Apoorva Ramesh

Name: Apoorva Ramesh

Title: Vice President

MORGAN STANLEY & CO. LLC

By: /s/ Jyri Wilska

Name: Jyri Wilska

Title: Managing Director

KEEFE, BRUYETTE & WOODS, INC.

By: /s/ Seth Bair

Name: Seth Bair

Title: Managing Director

[Signature Page to Underwriters’ Acceleration Request]

September 18, 2024
Stephen Sills
Chief Executive Officer
Bowhead Specialty Holdings Inc.
452 Fifth Avenue
New York, NY 10018
Re:Bowhead Specialty Holdings Inc.
Draft Registration Statement on Form S-1
Submitted September 10, 2024
CIK No. 0002002473
Dear Stephen Sills:
            This is to advise you that we do not intend to review your registration statement.
            We request that you publicly file your registration statement no later than 48 hours prior to
the requested effective date and time. Please refer to Rules 460 and 461 regarding requests for
acceleration. We remind you that the company and its management are responsible for the
accuracy and adequacy of their disclosures, notwithstanding any review, comments, action or
absence of action by the staff.
            Please contact Aisha Adegbuyi at 202-551-8754 with any questions.
Sincerely,
Division of Corporation Finance
Office of Finance
cc:Dwight S. Yoo, Esq.

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J.P. Morgan Securities LLC

383 Madison Avenue

New York, New York 10179

Morgan Stanley & Co. LLC

1585 Broadway

New York, New York 10036

Keefe, Bruyette & Woods, Inc.

787 Seventh Avenue

New York, New York 10019

May 20, 2024

VIA EDGAR

Securities and Exchange Commission

Division of Corporation Finance

100 F Street, N.E.

Washington, D.C. 20549-3561

Attention:    Aisha Adegbuyi

Re: Bowhead Specialty Holdings Inc.

Registration Statement on Form S-1

File No. 333-278653

Acceleration Request

Requested Date: May 22, 2024

Requested Time: 4:30 P.M. Eastern Time

Dear Ms. Adegbuyi:

In accordance with Rule 461 under the Securities Act of 1933, as amended (the “Act”), we, as representatives of the several underwriters, hereby join in the request of Bowhead Specialty Holdings Inc. (the “Company”) for acceleration of the effective date of the above-referenced Registration Statement, requesting effectiveness as of 4:30 P.M., Eastern Time, on May 22, 2024, or as soon thereafter as practicable or at such later time as the Company or its outside counsel, Skadden, Arps, Slate, Meagher & Flom LLP, may request via telephone call to the staff of the Division of Corporation Finance of the Securities and Exchange Commission.

Pursuant to Rule 460 under the Act, please be advised that we, as representatives of the several underwriters, will take reasonable steps to secure adequate distribution of the preliminary prospectus, to underwriters, dealers, institutions and others, prior to the requested effective time of the Registration Statement.

We, the undersigned, as representatives of the several underwriters, have complied and will comply, and we have been informed by the participating underwriters that they have complied and will comply, with the requirements of Rule 15c2-8 under the Securities Exchange Act of 1934, as amended.

[Signature Page Follows]

Very truly yours,

J.P. MORGAN SECURITIES LLC

By: /s/ Apoorva Ramesh

Name: Apoorva Ramesh

Title: Vice President

MORGAN STANLEY & CO. LLC

By: /s/ Jyri Wilska

Name: Jyri Wilska

Title:  Managing Director

KEEFE, BRUYETTE & WOODS, INC.

By: /s/ Seth Bair

Name: Seth Bair

Title: Managing Director

[Signature Page to Underwriters’ Acceleration Request]

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SKADDEN, ARPS, SLATE, MEAGHER & FLOM LLP

 ONE MANHATTAN WEST FIRM/AFFILIATE OFFICES

 ---------

BOSTON

CHICAGO

HOUSTON

LOS ANGELES

PALO ALTO

WASHINGTON, D.C.

WILMINGTON

---------

BEIJING

BRUSSELS

FRANKFURT

HONG KONG

LONDON

MUNICH

PARIS

SÃO PAULO

SEOUL

SHANGHAI

 NEW YORK, NY 10001

 ____

 TEL: (212) 735-3000

 FAX: (212) 735-2000

 www.skadden.com

 May 20, 2024

BY EDGAR

Securities and Exchange Commission

Division of Corporation Finance

100 F Street, N.E.

Washington, DC 20549-3561

Attn: Ms. Aisha Adegbuyi

 Attorney Advisor

Re: Bowhead Specialty Holdings Inc.

 Amendment No. 2 to

 Registration Statement on Form S-1

 Filed on May 13, 2024

 File No. 333-278653

Dear Ms. Adegbuyi:

On behalf of our client Bowhead Specialty Holdings Inc. (the “Company”), we hereby provide responses to comments received from the staff (the “Staff”) of the Securities and Exchange Commission (the “Commission”) by letter dated May 16, 2024 (the “Comment Letter”) with respect to the above-referenced Amendment No. 2 to Registration Statement on Form S-1 filed on May 13, 2024.

Concurrently with the submission of this letter, the Company is filing, through the Commission’s Electronic Data Gathering, Analysis and Retrieval system (“EDGAR”), Amendment No. 3 to the above mentioned Registration Statement on Form S-1 (the “Amendment No. 3”).

The headings and paragraph numbers in this letter correspond to those contained in the Comment Letter and, to facilitate the Staff’s review, we have reproduced the text of the Staff’s comments in italics below. Capitalized terms used but not defined herein have the meanings given to them in the Amendment No. 3. All references to page numbers and captions (other than those in the Staff’s comments and unless otherwise stated) correspond to the page numbers and captions in the Amendment No. 3.

Ms. Aisha Adegbuyi

Securities and Exchange Commission

May 20, 2024

Page 2

Management's Discussion and Analysis of Financial Condition and Results of Operations, page 62

1.We note your response to prior comment 2 and revised disclosure on page 64. You appear to have removed reference to other drivers previously noted, such as premium retention rates for existing business, the addition of new products, etc., while the revised discussion only addresses approximately half of the increase in gross written premiums experienced between the periods presented. Please revise your disclosures to also disclose and quantify any additional material drivers of period-over-period gross written premium increase. As it relates to the growth, quantify and disclose the growth attributed to each of your distribution channels. In this regard, we refer to your chart on page 86 disclosing that 33% and 67% of your gross written premiums are through Retail and Wholesale distribution channels, respectively, for the year ended December 31, 2023. Include similar updates to your discussion on page 61 for the three months ended March 31, 2024.

The Company revised the disclosure on pages 61 and 65 in response to the Staff’s comment.

Underwriting, page 140

2.We note your disclosure on page 141 that "[t]he underwriters have agreed to reimburse certain of our expenses in connection with the offering." Please revise this section to disclose the specific expenses that the underwriters have agreed to reimburse or advise.

The Company revised the disclosure on page 148 in response to the Staff’s comment.

* * * * *

Ms. Aisha Adegbuyi

Securities and Exchange Commission

May 20, 2024

Page 3

Please contact me at (212) 735-2573 or Dwight.Yoo@skadden.com if the Staff has any questions or requires additional information.

 Very truly yours,

 /s/ Dwight S. Yoo

cc: Christian Windsor, Securities and Exchange Commission

 Cara Lubit, Securities and Exchange Commission

 Robert Klein, Securities and Exchange Commission

 Stephen Sills, Chief Executive Officer, Bowhead Specialty Holdings Inc.

 Brad Mulcahey, Chief Financial Officer, Bowhead Specialty Holdings Inc.

 H. Matthew Crusey, General Counsel, Bowhead Specialty Holdings Inc.

 Todd E. Freed, Skadden, Arps, Slate, Meagher & Flom LLP

 Laura Kaufman Belkhayat, Skadden, Arps, Slate, Meagher & Flom LLP

 Marc D. Jaffe, Latham & Watkins LLP

 Erika L. Weinberg, Latham & Watkins LLP

 Gary D. Boss, Latham & Watkins LLP

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BOWHEAD SPECIALTY HOLDINGS INC.

1411 Broadway, Suite 3800

New York, New York 10018

May 20, 2024

BY EDGAR

Securities and Exchange Commission

Division of Corporation Finance

100 F Street, N.E.

Washington, DC 20549-3561

Attn: Aisha Adegbuyi

Re:      Bowhead Specialty Holdings Inc.

Registration Statement on Form S-1

Filed on May 13, 2024

File No. 333-278653

Dear Ms. Adegbuyi:

Pursuant to Rule 461 under the Securities Act of 1933, we respectfully request that the effective date of the registrant's Registration Statement on Form S-1 (File No. 333-278653) be accelerated by the Securities and Exchange Commission to 4:30 p.m. E.T. on May 22, 2024, or as soon as practicable thereafter, or at such other time as the registrant or its legal counsel may request by telephone to the staff of the Securities and Exchange Commission.

We request that we be notified of such effectiveness by a telephone call to Dwight Yoo of Skadden, Arps, Slate, Meagher & Flom LLP at (212) 735-2573 and that such effectiveness also be confirmed in writing.

Very truly yours,

BOWHEAD SPECIALTY HOLDINGS INC.

By: /s/ Brad Mulcahey

Name: Brad Mulcahey

Title: Chief Financial Officer

cc: Stephen Sills, Chief Executive Officer, Bowhead Specialty Holdings Inc.

H. Matthew Crusey, General Counsel, Bowhead Specialty Holdings Inc.

Dwight Yoo, Skadden, Arps, Slate, Meagher & Flom LLP

Todd E. Freed, Skadden, Arps, Slate, Meagher & Flom LLP

Laura Kaufman Belkhayat, Skadden, Arps, Slate, Meagher & Flom LLP

Marc D. Jaffe, Latham & Watkins LLP

Erika L. Weinberg, Latham & Watkins LLP

Gary D. Boss, Latham & Watkins LLP

United States securities and exchange commission logo
May 16, 2024
Stephen Sills
Chief Executive Officer
Bowhead Specialty Holdings Inc.
1411 Broadway, Suite 3800
New York, NY 10018
Re:Bowhead Specialty Holdings Inc.
Amendment No. 2 to
Registration Statement on Form S-1
Filed May 13, 2024
File No. 333-278653
Dear Stephen Sills:
            We have reviewed your registration statement and have the following comments.
            Please respond to this letter by amending your registration statement and providing the
requested information. 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 any amendment to your registration statement and the information you
provide in response to this letter, we may have additional comments.
Amendment No. 2 to Registration Statement on Form S-1
Management's Discussion and Analysis of Financial Condition and Results of Operations
Premiums, page 62
1.We note your response to prior comment 2 and revised disclosure on page 64. You appear
to have removed reference to other drivers previously noted, such as premium retention
rates for existing business, the addition of new products, etc., while the revised discussion
only addresses approximately half of the increase in gross written premiums experienced
between the periods presented. Please revise your disclosures to also disclose and quantify
any additional material drivers of period-over-period gross written premium increase. As
it relates to the growth, quantify and disclose the growth attributed to each of your
distribution channels. In this regard, we refer to your chart on page 86 disclosing that 33%
and 67% of your gross written premiums are through Retail and Wholesale distribution
channels, respectively, for the year ended December 31, 2023. Include similar updates to
your discussion on page 61 for the three months ended March 31, 2024.

 FirstName LastNameStephen Sills
 Comapany NameBowhead Specialty Holdings Inc.
 May 16, 2024 Page 2
 FirstName LastName
Stephen Sills
Bowhead Specialty Holdings Inc.
May 16, 2024
Page 2
Underwriting, page 140
2.We note your disclosure on page 141 that "[t]he underwriters have agreed to reimburse
certain of our expenses in connection with the offering." Please revise this section to
disclose the specific expenses that the underwriters have agreed to reimburse or advise.

            We remind you that the company and its management are responsible for the accuracy
and adequacy of their disclosures, notwithstanding any review, comments, action or absence of
action by the staff.
            Refer to Rules 460 and 461 regarding requests for acceleration. Please allow adequate
time for us to review any amendment prior to the requested effective date of the registration
statement.
            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.

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SKADDEN, ARPS, SLATE, MEAGHER & FLOM LLP

 ONE MANHATTAN WEST FIRM/AFFILIATE OFFICES

 ---------

BOSTON

CHICAGO

HOUSTON

LOS ANGELES

PALO ALTO

WASHINGTON, D.C.

WILMINGTON

---------

BEIJING

BRUSSELS

FRANKFURT

HONG KONG

LONDON

MUNICH

PARIS

SÃO PAULO

SEOUL

SHANGHAI

SINGAPORE

TOKYO

TORONTO

 NEW YORK, NY 10001

 ____

 TEL: (212) 735-3000

 FAX: (212) 735-2000

 www.skadden.com

 May 3, 2024

BY EDGAR

Securities and Exchange Commission

Division of Corporation Finance

100 F Street, N.E.

Washington, DC 20549-3561

Attn: Ms. Aisha Adegbuyi

 Attorney Advisor

 Re: Bowhead Specialty Holdings Inc.

  Registration Statement on Form S-1

  Filed on April 12, 2024

  File No. 333-278653

Dear Ms. Adegbuyi:

On behalf of our client Bowhead Specialty Holdings Inc. (the “Company”), we hereby provide responses to comments received from the staff (the “Staff”) of the Securities and Exchange Commission (the “Commission”) by letter dated April 18, 2024 (the “Comment Letter”) with respect to the above-referenced Registration Statement on Form S-1 filed on April 12, 2024.

Concurrently with the submission of this letter, the Company is filing, through the Commission’s Electronic Data Gathering, Analysis and Retrieval system (“EDGAR”), Amendment No. 1 to the above mentioned Registration Statement on Form S-1 (the “Amendment No. 1”).

The headings and paragraph numbers in this letter correspond to those contained in the Comment Letter and, to facilitate the Staff’s review, we have reproduced the text of the Staff’s comments in italics below. Capitalized terms used but not defined herein have the meanings given to them in the Amendment No. 1. All references to page numbers and captions (other than those in the Staff’s comments and unless otherwise stated) correspond to the page numbers and captions in the Amendment No. 1.

Ms. Aisha Adegbuyi

Securities and Exchange Commission

May 3, 2024

Page 2

Prospectus Summary

Who We Are, page 1

1.We note your response to prior comment 1 and revised disclosures on pages 47 and 116 that discuss, among other things, the new contractual terms with AmFam. However, it is unclear how these new contractual terms compare to the current AmFam arrangement terms that have been in place for the financial statement periods presented. Please revise your disclosures where applicable to address the items below, or tell us where this information is already disclosed.

•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. Discussion should include, but not be limited to: fee terms; 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.

•To the extent that your new arrangement terms with AmFam differ from your prior arrangement, disclose such differences or state that none exist.

The Company revised the disclosure on pages 118, 119 and 120 in response to the Staff’s comment.

Management's Discussion and Analysis of Financial Condition and Results of Operations

Premiums, page 58

2.We note your disclosures on page 58 regarding the drivers of gross written premium increase from 2022 to 2023. Please expand your disclosures to quantify the impact of each key driver and to provide some additional detail, such as clarifying the proportion of volume from existing versus new distribution partners, quantifying "strong" premium retention rates, and identifying new products and expanded offerings. Refer to Item 303(b)(2) of Regulation S-K.

The Company revised the disclosure on page 62 in response to the Staff’s comment.

Reconciliation of Non-GAAP Financial Measures, page 59

3.We note your adjustment to exclude strategic initiative expenses incurred to set up your Baleen Specialty initiative. Please expand your disclosures to clarify the nature of the expenses and where they are reflected in your financial statements.

The Company revised the disclosure on page 64 in response to the Staff’s comment.

* * * * *

Ms. Aisha Adegbuyi

Securities and Exchange Commission

May 3, 2024

Page 3

Please contact me at (212) 735-2573 or Dwight.Yoo@skadden.com if the Staff has any questions or requires additional information.

Very truly yours,

/s/ Dwight S. Yoo

cc: Christian Windsor, Securities and Exchange Commission

 Cara Lubit, Securities and Exchange Commission

 Robert Klein, Securities and Exchange Commission

 Stephen Sills, Chief Executive Officer, Bowhead Specialty Holdings Inc.

 Brad Mulcahey, Chief Financial Officer, Bowhead Specialty Holdings Inc.

 H. Matthew Crusey, General Counsel, Bowhead Specialty Holdings Inc.

 Todd E. Freed, Skadden, Arps, Slate, Meagher & Flom LLP

 Laura Kaufman Belkhayat, Skadden, Arps, Slate, Meagher & Flom LLP

 Marc D. Jaffe, Latham & Watkins LLP

 Erika L. Weinberg, Latham & Watkins LLP

 Gary D. Boss, Latham & Watkins LLP

United States securities and exchange commission logo
April 18, 2024
Stephen Sills
Chief Executive Officer
Bowhead Specialty Holdings Inc.
1411 Broadway, Suite 3800
New York, NY 10018
Re:Bowhead Specialty Holdings Inc.
Registration Statement on Form S-1
Filed April 12, 2024
File No. 333-278653
Dear Stephen Sills:
            We have reviewed your registration statement and have the following comments.
            Please respond to this letter by amending your registration statement and providing the
requested information. 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 any amendment to your registration statement and the information you
provide in response to this letter, we may have additional comments. Unless we noteotherwise,
our references to prior comments are to comments in our February 21, 2024 letter.
Registration Statement on Form S-1
Prospectus Summary
Who We Are, page 1
1.We note your response to prior comment 1 and revised disclosures on pages 47 and
116 that discuss, among other things, the new contractual terms with AmFam. However, it
is unclear how these new contractual terms compare to the current AmFam arrangement
terms that have been in place for the financial statement periods presented. Please revise
your disclosures where applicable to address the items below, or tell us where this
information is already disclosed.
•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. Discussion should include, but not be
limited to: fee terms; whether any authority parameters exist; how decisions are
made; details of any termination provisions; and whether there is a right of refusal or

 FirstName LastNameStephen Sills
 Comapany NameBowhead Specialty Holdings Inc.
 April 18, 2024 Page 2
 FirstName LastName
Stephen Sills
Bowhead Specialty Holdings Inc.
April 18, 2024
Page 2
denial by either entity.
•To the extent that your new arrangement terms with AmFam differ from your prior
arrangement, disclose such differences or state that none exist.
Management's Discussion and Analysis of Financial Condition and Results of Operations
Premiums, page 58
2.We note your disclosures on page 58 regarding the drivers of gross written premium
increase from 2022 to 2023. Please expand your disclosures to quantify the impact of each
key driver and to provide some additional detail, such as clarifying the proportion of
volume from existing versus new distribution partners, quantifying "strong" premium
retention rates, and identifying new products and expanded offerings. Refer to Item
303(b)(2) of Regulation S-K.
Reconciliation of Non-GAAP Financial Measures, page 59
3.We note your adjustment to exclude strategic initiative expenses incurred to set up your
Baleen Specialty initiative. Please expand your disclosures to clarify the nature of the
expenses and where they are reflected in your financial statements.
            We remind you that the company and its management are responsible for the accuracy
and adequacy of their disclosures, notwithstanding any review, comments, action or absence of
action by the staff.
            Refer to Rules 460 and 461 regarding requests for acceleration. Please allow adequate
time for us to review any amendment prior to the requested effective date of the registration
statement.
            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.

United States securities and exchange commission logo
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,

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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.

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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.

United States securities and exchange commission logo
January 17, 2024
Stephen Sills
Chief Executive Officer
Bowhead Holdings Inc.
1411 Broadway, Suite 3800
New York, NY 10018
Re:Bowhead Holdings Inc.
Draft Registration Statement on Form S-1
Submitted December 21, 2023
CIK No. 0002002473
Dear Stephen Sills:
            We have reviewed your registration statement and have the following comments.
            Please respond to this letter by amending your registration statement and providing the
requested information. 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 any amendment to your registration statement and the information you
provide in response to this letter, we may have additional comments.
Draft Registration Statement on Form S-1
General
1.Please provide us with supplemental copies of all written communications, as defined in
Rule 405 under the Securities Act, that you, or anyone authorized to do so on your behalf,
have presented or expect to present to potential investors in reliance on Section 5(d) of the
Securities Act, whether or not you retained, or intend to retain, copies of those
communications. Please contact Aisha Adegbuyi at (202) 551-8754 to discuss how to
submit the materials, if any, to us for our review.
2.We note that press coverage of Bowhead discusses a number of points of connection with
your two largest shareholders that do not appear to have been discussed in the draft
registration statement. For instance, we note that trade publications state that "[t]he
partnership with American Family is understood . . . [to have] an option for the US insurer
to buy Bowhead Specialty." Please tell us whether the reporting is accurate related to any
purchase options for American Family or any of your other controlling shareholders.  To
the extent that the reporting is accurate, please tell us whether these purchase obligations

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will remain after the completion of the pre-IPO reorganizations contemplated in the draft
registration statement, and make appropriate revisions if necessary.
A Letter From Our Founder and Chief Executive, page vi
3.In order to present the discussion by Mr. Sills in the appropriate context, including a
discussion of Bowhead's business, please move this letter so that it appears after the
prospectus summary.
Prospectus Summary, page 1
4.This document appears to have been written for a reader who is conversant with the
insurance business. For instance, we note that you use several shortened descriptions for
key concepts related to the markets that you serve, and the products that you sell. For
instance, we note that you use the term GL, for general liability, and FI, for financial
institutions, without explaining the term or how it might impact your business and the
risks of the products you sell. Please revise the prospectus summary to provide
appropriate explanations of your business and the terms used, to allow a reader to
understand your business, and the more detailed discussions you present in the risk factors
and business sections.
Who We Are, page 1
5.We note your disclosures regarding the domiciles, nature, and licenses of your subsidiary
entities. We also note your disclosure regarding your ability to write business through
your relationship with AMFIC and its subsidiaries. Please revise your disclosures to
explicitly clarify whether your own legal entity licensures and statuses are sufficient to
permit you to write business on a standalone basis or whether your ability to write
business is predicated on your relationship with AMFIC and its subsidiaries.
6.We note your disclosure on page 2 and elsewhere that you originate business “on the
paper” of AmFam. Please tell us and revise your disclosures to fully explain what this
means. In addition, provide a more fulsome discussion of the contractual terms and rights
between you and AmFam under this arrangement, such as fee terms, whether any
authority parameters exist, how decisions are made and whether there is a right of refusal
or denial by either entity.

Our Business, page 2
7.We note your disclosure, here and on page 68, regarding gross written premiums by
underwriting division and product for the year ended December 31, 2022. Please revise
your disclosures in an appropriate location to also address any geographic concentrations
(such as states) for your policies, as applicable.

8.We note your disclosures, such as on page 6, that you “go to market” under the Bowhead

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brand. We also note your disclosure, such as on page 9, that you go to market leveraging
AmFam’s legal entities, ratings, and licenses through your agreements with AMFIC.
Please revise your disclosures, here or elsewhere, to clarify what you mean in each
context and to clarify the distinction between the two statements.
9.We note your disclosures regarding products/solutions offered by your divisions. Please
revise your disclosures to clarify, here or elsewhere, as appropriate, whether any of your
policies cover physical damage and, if so, quantify the proportion covering physical
damage versus liability.
Our Structure, page 9
10.We note that a trade publication, Program Manager, in an article posted on October 16,
2023, indicated that your agreement with American Family runs through 2026. To the
extent that this reporting is accurate, revise your disclosure to indicate the current term of
your agreement. Also, disclose the extent to which negotiations for an extension have
occurred, or are ongoing, and whether the extension will be in place before the IPO. Make
conforming changes to your risk factor on page 17.
11.Revise your presentation to show your organizational structure after the
reorganization. Ensure that you reflect the ownership interests of purchasers in
the offering contemplated by this draft registration statement.
12.We note that your two main shareholders, Gallatin and American Family, both have a
number of other business interests in the insurance business. Please tell us, with a view
towards revised disclosure, whether either of your controlling shareholders have any
restrictions on their ability to compete with Bowhead in your main lines of insurance, or
to offer employment to existing or future key Bowhead employees.
Summary of Risk Factors, page 10
13.Revise the summary to highlight the most significant risks to investors in your business.
We note that the existing summary does not discuss your status as a controlled company,
but does include a relatively in-depth discussion of your status as an emerging growth
company.
Risk Factors
Inability to maintain our strategic relationship with AmFam would materially adversely affect
our business., page 17
14.We note your disclosures that you rely on your strategic partnership with AmFam and that
related contractual arrangements may terminate or be terminated under certain
circumstances. Please revise your disclosures, here or elsewhere as appropriate, to provide
additional detail regarding terminations of these arrangements, such as but not limited to
the circumstances in which the contractual arrangements may be terminated; whether such
terminations could be initiated by you, AmFam, or either party; and how much (if any)

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advance notice you would receive before termination.
A decline in AmFam's financial strength rating or financial size category may adversely affect
our financial condition . . ., page 18
15.We note your disclosure that you do not currently have a standalone A.M. Best rating for
BICI and that you leverage AmFam’s A.M. Best rating for certain lines of business.
Please revise your disclosures to explain what business, if any, you would be unable to
conduct if the contractual relationship with AmFam were terminated, and to quantify this
in the context of your overall operations.
Our losses and loss expense reserves may be inadequate..., page 20
16.We note your disclosure on page 75 that "[you] underwrite business on both an admitted
and E&S basis, depending on the specific product and segments that we target." You go
on to say on page 78 that you "predominantly write non-admitted business in the E&S
market." Revise this risk factor to indicate whether your choice to primarily write non-
admitted policies contributes to the uncertainty related to your loss reserves.
Adverse economic factors, including recession, inflation . . . could result in the sale of fewer
policies than expected . . ., page 25
17.We note your disclosure on page 25 that "factors, such as business revenue, economic
conditions, the volatility and strength of the capital markets and inflation can affect the
business and economic environment." Please update this risk factor to reflect how recent
inflationary pressures impacted your operations. In this regard, identify the types of
inflationary pressures you are facing and how your business has been affected.
The insurance business is historically cyclical in nature, which may affect our financial
performance . . ., page 26
18.Please clarify in this risk factor, and its subheading, where the insurance industry currently
is in terms of its cyclical nature so that investors may assess the risk. Additionally, please
clarify which programs and lines of business you believe are impacted or not significantly
impacted by the hard and soft market cycles you discussed. Furthermore, discuss the
extent to which management believes that you have experienced the key elements of the
cycle since you began operations in 2020.
We are subject to extensive regulation, which may adversely affect our ability to achieve our
business objectives., page 28
19.We note your disclosure on page 29 and elsewhere (such as the Risk-Based Capital
section) that you are subject to certain requirements under a company-specific stipulation
and order from the Wisconsin OCI. Please revise your disclosures, here and elsewhere as
appropriate, to explain the nature of this company-specific stipulation and order, such as
what prompted its issuance; when it was put in place; how long it will be in place, if

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known; and what other terms within it, if any, restrict or impact your operations, and how.
We could be adversely affected by the loss of one or more key personnel . . ., page 30
20.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.
Our management will have broad discretion over the use of the proceeds we receive in this
offering . . ., page 39
21.We note your disclosure that "[your] management will have broad discretion in the
application of the net proceeds from the sale of shares by [you] in this offering, including
for any of the purposes described in the section entitled 'Use of Proceeds,' and [investors]
will not have the opportunity as part of [their] investment decision to assess whether the
net proceeds are being used appropriately." To the extent that you have a use in mind for
the net proceeds, disclose it or clarify what you mean by this statement to give investors
the ability to better understand the possible risks.
Our amended and restated certificate of incorporation . . . , page 41
22.We note your disclosure on page 41 that "[your] amended and restated certificate of
incorporation further will provide that, unless [you] consent in writing to the selection of
an alternative forum, to the fullest extent permitted by law, the federal district courts of
the United States of America will be the exclusive forum for the resolution of any
complaint asserting a cause of action arising under the federal securities laws of the
United States, including any claims under the Securities Act and the Exchange
Act." Please also state that investors cannot waive compliance with the federal securities
laws and the rules and regulations thereunder.
Management’s Discussion and Analysis of Financial Condition and Results of Operations
Liquidity and Capital Resources
Reinsurance, page 58
23.We note your disclosures on page 59 that your Cyber line of business uses different quota
share reinsurance and excess of loss reinsurance treaties from those used by your other
lines of business. We also note your disclosure of the Cyber quota share structure. Please
revise your disclosures to also discuss the Cyber business’s excess of loss reinsurance
treaty arrangements or to clarify, if true, that no excess of loss arrangements are currently
in place for that line of business.

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Quantitative and Qualitative Disclosures about Market Risk, page 61
24.We note that your sensitivity analysis for your interest rate risk exposure assumes a 100-
basis point increase/decrease in interest rates. Please tell us how you determined that 100-
basis points was an appropriate measurement point for the possible impact of an increase
or decrease in interest rates, particularly given the changes in interest rates experienced in
the past 12 months.

Business, page 67
25.We note your risk factor disclosure on page 18, that you are dependent on a key group of
brokers to distribute your policies to potential clients. We also note that you discuss your
key brokers in Note 12, disclosing your largest relationships on page F-22. Revise this
section, or another section, to discuss how you manage your broker relationships,
including evaluating possible credit risk and renewal activities of your current key broker
partners, as well as efforts to recruit additional brokers.
Competition, page 83
26.We note your disclosure that "some of [y]our notable competitors include: American
International Group, Inc., Arch Capital Group Ltd., AXA S.A., Axis Capital Holdings
Ltd., Berkshire Hathaway Corporation, C.V. Starr & Co., Inc., Chubb Ltd., Cincinnati
Financial Corporation, CNA Financial Corporation, Liberty Mutual Insurance Company,
Nationwide Mutual Insurance Company, The Doctors Company, The Travelers
Companies, Inc. and W.R. Berkley Corporation." Please provide the criteria you used to
identify these companies as your competitors.
Human Capital, page 83
27.We note your disclosure that "[a]s of November 30, 2023, [you] had over 190
employees." Please tell us, with a view towards revised disclosure, the reason why you
cannot be precise about the total number of employees as of November 30, 2023.
Regulation
IRIS Ratios, page 89
28.We note your disclosure that "[a]s of December 31, 2022, BICI had results outside the
normal range in four categories. [Your] results for these ratios are attributable to the
significant growth in premiums and low investment yields due to the current interest rate
environment. Management does not anticipate regulatory action as a result of these IRIS
ratio result