THIS INVESTOR MATTERS AGREEMENT (this “Agreement”) dated as of May 23, 2024, is by and between Bowhead Specialty Holdings Inc., a Delaware corporation (the “Company”), and American Family Mutual Insurance Company, S.I., a Wisconsin corporation (the “Investor”) (the Company and the Investor, each a “Party” and together, the “Parties”). Capitalized terms used herein shall have the meanings set forth in Section 5 of this Agreement.

WHEREAS, on May 13, 2024, the Company launched an initial public offering of its shares of common stock (“Company Common Stock”) pursuant to a registered underwritten public offering (the “Company IPO”);

WHEREAS, as of the consummation of the Company IPO, the Investor will own (a) 26.1% of the outstanding Class A Interests (as defined in the Amended & Restated LPA) of BIHL, which entitles the Investor, upon completion of the Reorganization Transaction, to a number of shares of Company Common Stock and (ii) a warrant to purchase 1,614,250 shares of Company Common Stock (or up to 1,670,721 shares of Company Common Stock if the underwriters’ over-allotment option in connection with the Company IPO is exercised in full) (the “Warrant”); and

1.    Maintenance of Ownership. During the period beginning on the date of this Agreement and ending on the third (3rd) anniversary thereof (the “Maintenance Period”), the Investor (i) shall maintain (A) at all times prior to the completion of the Reorganization Transaction, ownership of Class A Interests of BIHL that would entitle the Investor upon completion of the Reorganization Transaction to a number of shares of Company Common Stock equal to at least ten percent (10%) of the issued and outstanding shares of Company Common Stock (which shares owned by the Investor shall include shares subject to the Warrant, to the extent vested (assuming there is no cashless exercise)) and (B) at all times following the completion of the Reorganization Transaction, ownership of shares of Company Common Stock equal to at least ten percent (10%) of the issued and outstanding shares of Company Common Stock (which shares owned by the Investor shall include shares subject to the Warrant, to the extent vested (assuming there is no cashless exercise)) (each of the amounts set forth in clause (A) and (B), the “Minimum Ownership Amount”), (ii) shall report the Company and each of the Company’s wholly owned subsidiaries as an Affiliate for all insurance statutory accounting and regulatory purposes, (iii) for purposes of the Reinsurance Agreement, shall treat BIC as an Affiliate, and (iv) shall not make any filing with, or make any communication (written or oral) to, any Governmental Authority, or take any other action, that would reasonably be likely to result in the Investor no longer being deemed an Affiliate of the Company; provided, however, that in no event shall the Investor be required to acquire additional Class A Interests or shares of Company Common Stock in the event additional interests in BIHL are issued or the Company issues additional shares. Subject to the foregoing proviso, during the Maintenance Period, the Investor agrees that BIC shall be entitled to treat the Investor as an Affiliate for all insurance statutory accounting and regulatory purposes. For purposes of this Section 1, “Affiliate” of the Company or of BIC shall have the meaning ascribed to it under SSAP No. 88, Investments in Subsidiary, Controlled, and Affiliated Entities.

2.    Board Representatives.

the “Representation Expiration Date”), at every applicable annual meeting of the stockholders of the Company in which directors are generally elected (or special meeting in lieu of an annual meeting at which directors are to be elected and adjusted as appropriate to take into account the Company’s classified Board structure), the Investor shall have the right to recommend to the Company (A) one (1) individual to serve as a Class I director and (B) one (1) individual to serve as a Class II director (such individuals, the “Board Nominees” and each a “Board Nominee”) on the Board of Directors of the Company (the “Board”); provided, however, that any such director nominee shall be reasonably satisfactory to the applicable committee of the Board with authority over nominations of individuals to serve as directors of the Company. Each of Troy Van Beek and David Holman shall be a Board Nominee for purposes of this Agreement, including Section 2(h), such persons having been deemed to be reasonably satisfactory to the applicable committee of the Board with authority over nominations of individuals to serve as directors of the Company.

(b)    If the Investor is no longer entitled to two (2) Board Nominees in accordance with the foregoing Section 2(a), then so long as the Investor continues to own the Minimum Ownership Amount, at every applicable annual meeting of the stockholders of the Company in which directors are generally elected (or special meeting in lieu of an annual meeting at which directors are to be elected and adjusted as appropriate to take into account the Company’s classified Board structure), the Investor shall have the right to recommend to the Company one individual to serve as a Class I director of the Company as a Board Nominee; provided, however, that any such director nominee shall be reasonably satisfactory to the applicable committee of the Board with authority over nominations of individuals to serve as directors of the Company.

(c)    If any Board Nominee is deemed not reasonably satisfactory in accordance with the foregoing paragraphs, the Investor will be given a reasonable opportunity to select another individual to serve as Board Nominee. If any Board Nominee is not elected by the stockholders at any annual meeting held during the period in which the Investor is entitled to Board Nominees pursuant to the foregoing Section 2(a) or 2(b), then as soon as practicable after the annual meeting, the applicable Board Nominee (or such other person acceptable to the Investor and the Board) shall be appointed as a director by the Board promptly following such annual meeting to the same class as the applicable Board Nominee were originally nominated for. In addition, if a vacancy is created on the Board as a result of the death, disability, retirement, resignation (other than a resignation required by Section 2(h)) or removal of a Board Nominee, then the Investor shall have the right to recommend such person’s replacement to be appointed to the same class as the applicable Board Nominee prior to the next annual meeting of stockholders, which recommendation shall be considered in good faith by the Board. For the avoidance of doubt, each reference in this Section 2(d) to “annual meeting” shall also be deemed a reference to a special meeting held in lieu of an annual meeting during the period in which the Investor is entitled to Board Nominees pursuant to this Agreement.

(d)    For so long as the Investor has the right to nominate any nominee(s) for election as a Class I or Class II director pursuant to this Section 2 (subject to the provisos in Section 2(a) and 2(b) above), the Company shall nominate such nominee(s) for election as a director as part of the applicable slate that is included in the proxy statement (or consent solicitation or similar document) of the Company (or such other person) relating to the election of directors, and shall provide the highest level of support for the election of such nominee(s), as the case may be, as it provides to any other individual standing for election as a director of the Company (or such other person) as part of the Company’s (or such other person’s) slate of directors.

(g)    Notwithstanding anything to the contrary herein, the Investor’s right to recommend the Board Nominee(s) pursuant to Section 2(a) and 2(b) and all related rights of the Investor and obligations of the Company set forth in this Section 2 shall terminate immediately upon the termination of the Reinsurance Agreement and the MGA Agreements (notwithstanding any continuing provisions in Section 4.05 of the Reinsurance Agreement or Section 14.9 of the MGA Agreements) at any time prior to the five (5) year anniversary of the consummation of the Company IPO.

(h)    In the event (i) the Representation Expiration Date shall occur, (ii) the Investor fails to maintain the Minimum Ownership Amount or (iii) this Agreement terminates pursuant to Section 2(g), then each Board Nominee shall promptly offer to resign from the Board and, if requested by the Company, promptly deliver his or her written resignation to the Board (which shall provide for his or her immediate resignation), it being understood that it shall be in the Board’s sole discretion whether to accept or reject such resignation; provided, however, if two Board Nominees are on the Board and the Investor continues to have the right to one Board Nominee pursuant to Section 2(b), then only the current Class II Board Nominee shall promptly offer to resign from the Board and, if requested by the Company, promptly deliver his or her written resignation to the Board (which shall provide for his or her immediate resignation), it being understood that it shall be in the Board’s sole discretion whether to accept or reject such resignation. The Investor agrees to cause the Board Nominees to resign from the Board if the Board Nominees fail to resign if and when contemplated by this Section 2(h).

(i)    On and as of the date on which the Investor owns less than the Minimum Ownership Amount for any reason other than solely dilution resulting from the issuance of additional Common Stock by the Company where the Investor has not sold more than 35% of the shares of Common Stock held by the Investor following the date of this Agreement (or, if earlier terminated pursuant to Section 2(g), on and as of such termination date), all of the nomination rights of the Investor set forth in this Section 2 shall terminate in full and be of no further force or effect, regardless of any increase in the amount of Common Stock that the Investor owns after such date.

3.    MGA Agreements. The Parties hereby agree to take such actions as may be reasonably required to enter into amended and restated MGA Agreements consistent in all material respects with the terms of the managing general agency agreements approved by the Wisconsin Office of the Insurance Commissioner in its letter dated April 22, 2024 as soon as reasonably practicable following the consummation of the Company IPO, including, without limitation, the obtaining of any required insurance regulatory approvals for such amended and restated MGA Agreements.

4.    Change of Control Agreement. In the event the Company enters into an agreement within 12 months of the Company IPO that would ultimately result in a Change of Control (a) the result of which is the Company's common stock would no longer qualify for listing on the NYSE (such agreement, a “Change of Control Agreement”) and (b) involves an acquiring party identified in writing to the Company by Gallatin Point and the Investor as mutually agreed by Gallatin Point and the Investor, then the Investor would have the right to (i) renegotiate the terms of the Reinsurance Agreement and the MGA Agreements in connection with such Change of Control or (ii) terminate the Reinsurance Agreement and the MGA Agreements in connection with such Change of Control; provided, however, that in each such case such negotiated terms or termination shall only become effective upon the consummation of such Change of Control and if the such Change of Control Agreement is terminated, such renegotiated terms or termination right shall be null and void.

(i)    “Amended & Restated LPA” means that certain Amended and Restated Limited Partnership Agreement of BIHL, dated as of October 14, 2020, by and among the partners thereto, as amended from time to time.

(ii)    “BIC” means Bowhead Insurance Company Inc.

(iii)    “BIHL” means Bowhead Insurance Holdings LP, a Delaware limited partnership.

(iv)    “Business Day” means any day other than Saturday, Sunday and any day on which banking institutions in the State of New York are authorized or required by law to be closed.

(v)    “Change of Control” means (A) the sale, transfer, or other disposition of all or substantially all of the Company’s assets, (B) any merger, consolidation or other business combination transaction of the Company with or into another corporation, entity or person, other than a transaction in which the holders of at least a majority of the shares of voting capital stock of the Company outstanding immediately prior to such transaction continue to hold (either by such shares remaining outstanding or by their being converted into shares of voting capital stock of the surviving entity) a majority of the total voting power represented by the shares of voting capital stock of the Company (or the surviving entity) outstanding immediately after such transaction, or (C) the direct or indirect acquisition (including by way of a tender or exchange offer) by any person or persons acting as a group (other than by Gallatin Point or its affiliates (including any fund controlled by Gallatin Point or its affiliates)) of beneficial ownership or a right to acquire beneficial ownership of shares representing a majority of the voting power of the then outstanding shares of capital stock of the Company. A Change of Control shall not include (x) the Reorganization Transaction or (y) a transaction if its sole purpose is to change the state of the Company’s incorporation or to create a holding company that will be owned in substantially the same proportions by the persons who held the Company’s securities immediately before such transaction or solely as a result of any person or group of persons ceasing to own a majority of the voting power of the then outstanding shares of capital stock of the Company.

(vi)    “Class I director” has the meaning set forth in the Company’s amended and restated certificate of incorporation.

(vii)    “Class II director” has the meaning set forth in the Company’s amended and restated certificate of incorporation.

(viii)    “Gallatin Point” means GPC Partners Investments (SPV III) LP.

(ix)    “Governmental Authority” means any foreign or United States federal, state, provincial or local governmental, quasi-governmental, legislative, regulatory or administrative authority, agency, body, commission or other similar entity or any court, tribunal, or judicial or arbitral body.

(x)    “MGA Agreements” means collectively, (A) the Managing General Agency Agreement, dated as of February 1, 2021, by and between Homesite Insurance Company and Bowhead Specialty Underwriters, Inc. (the “Agent”), as amended from time to time; (B) the Amended and Restated Managing General Agency Agreement, dated April 1, 2022, by and between Homesite Insurance Company of Florida and the Agent, as amended from time to time, (C) the Managing General Agency Agreement, dated February 1, 2021, by and between Midvale Indemnity Company and the Agent, as amended from time to time; and (D) the Managing General Agency Agreement to be entered into in the second calendar quarter of 2024 by and between American Family Connect Reinsurance Company and the Agent, as amended from time to time.

(xi)    “Reinsurance Agreement” means the 100% Quota Share Reinsurance Agreement, dated as of January 1, 2021, by and between the Investor and BIC, as amended from time to time, including in connection with the Company IPO.

(xii)    “Reorganization Transaction” means the termination, liquidation and dissolution of BIHL, pursuant to which each of the holders of the Class A Interests and Class P Interests (each as defined in the Amended & Restated LPA) will receive a number of shares of Company Common Stock in accordance with the distribution provisions of the Amended & Restated LPA.

6.    Reorganization Transaction. The Company hereby agrees to take such actions with respect to itself and its subsidiaries as may be reasonably required to effect the Reorganization Transaction as soon as reasonably practicable following the consummation of the Company IPO, including, without limitation, the obtaining of any required insurance regulatory approvals for the Reorganization Transaction.

7.    Non-Circumvention. Each of the Parties hereby covenants and agrees that the Company will not, by amendment of its certificate of incorporation, bylaws or through any reorganization, transfer of assets, consolidation, merger, scheme of arrangement, dissolution, issue or sale of securities, or any other action, avoid or seek to avoid the observance or performance of any of the terms of this Agreement, and will at all times in good faith carry out all the provisions of this Agreement and, subject to the other provisions of this Agreement, take all action as may be reasonably required to protect the rights of the other Party hereto.

8.    Entire Agreement; No Third-Party Beneficiaries. This Agreement (a) constitutes the entire agreement, and supersedes all other prior agreements and understandings, both written and oral, among the Parties hereto with respect to such subject matter hereof and thereof and (b) is not intended to and shall not confer upon any Person other than the Parties hereto (and any Person that delivers an executed joinder agreement in accordance with this Agreement) any rights or remedies hereunder.

9.    Notices. All notices or other communications required or permitted to be given hereunder shall be in writing and shall be deemed to have been duly given (a) when delivered personally, (b) three (3) Business Days after being mailed by certified or registered mail, return receipt requested and postage prepaid, (c) when received, if sent by overnight delivery service or international courier or (d) when sent, if sent by email, provided that it is followed immediately by confirmation via personal delivery, overnight delivery service or international courier. A Party may change its address, number or email address for the purposes hereof upon written notice to the other Parties. Such notices or other communications shall be sent to each Party as follows:

10.    Specific Enforcement. The Parties agree that irreparable damage would occur in the event that any of the terms or provisions of this Agreement related to the matters contemplated hereby were not performed in accordance with their specific wording or were otherwise breached. It is accordingly agreed that, notwithstanding anything to the contrary contained in this Agreement, each of the Parties hereto shall be entitled to an injunction or injunctions to prevent such breaches of this Agreement and to enforce specifically the terms and provisions hereof, such remedy being in addition to any other remedy to which a Party may be entitled at law or in equity. Each Party further agrees that the only permitted objection that it may raise in response to any action for equitable relief is that it contests the existence of a breach or threatened breach of this Agreement.

11.    Severability. If any term or other provision of this Agreement is invalid, illegal or incapable of being enforced under any law or as a matter of public policy, all other conditions and provisions of this Agreement shall nevertheless remain in full force and effect so long as the economic or legal substance of the matters contemplated by this Agreement is not affected in any manner materially adverse to any Party. If any provision of this Agreement is so broad as to be unenforceable, that provision shall be interpreted to be only so broad as is enforceable. Upon such determination that any term or other provision is invalid, illegal or incapable of being enforced, the Parties to this Agreement shall negotiate in good faith to modify this Agreement so as to effect the original intent of the Parties as closely as possible in a mutually acceptable manner in order that the matters contemplated by this Agreement be consummated as originally contemplated to the greatest extent possible.

12.    Governing Law; Jurisdiction.

(b)    Each of the Parties hereby irrevocably and unconditionally (a) submits, for itself and its property, to the exclusive jurisdiction and venue of the Delaware Court of Chancery (or, only if the Delaware Court of Chancery does not have jurisdiction over a particular matter, the Superior Court of the State of Delaware (and the Complex Commercial Litigation Division thereof if such division has jurisdiction over the particular matter), or if the Superior Court of the State of Delaware does not have jurisdiction, any federal court of the United States of America sitting in the State of Delaware) (“Delaware Courts”), and any appellate court from any decision thereof, in any action arising out of or relating to this Agreement, including the negotiation, interpretation, execution or performance of this Agreement and agrees that all claims in respect of any such action shall be heard and determined in the Delaware Courts, (b) waives, to the fullest extent it may legally and effectively do so, any objection which it may now or hereafter have to the laying of venue of any action arising out of or relating to this Agreement or the negotiation, interpretation, execution or performance of this Agreement in the Delaware Courts, including any objection based on its place of incorporation or domicile, (c) waives, to the fullest extent permitted by law, the defense of an inconvenient forum to the maintenance of such action in any such court and (d) agrees that a final judgment in any such action shall be conclusive and may be enforced in other jurisdictions by suit on the judgment or in any other manner provided by law. Each of the Parties consents and agrees that service of process, summons, notice or document for any action permitted hereunder may be delivered by registered mail addressed to it at the applicable address set forth in Section 9 or in any other manner permitted by applicable law.

BY JURY FOR ANY DISPUTE BASED UPON, ARISING OUT OF OR RELATING TO THIS AGREEMENT OR THE BREACH, TERMINATION OR VALIDITY HEREOF OR ANY MATTERS CONTEMPLATED BY THIS AGREEMENT. EACH OF THE PARTIES CERTIFIES AND ACKNOWLEDGES THAT (1) NEITHER THE OTHER PARTY NOR ITS REPRESENTATIVES, AGENTS OR ATTORNEYS HAVE REPRESENTED, EXPRESSLY OR OTHERWISE, THAT SUCH OTHER PARTY WOULD NOT, IN THE EVENT OF LITIGATION, SEEK TO ENFORCE THE FOREGOING WAIVER, (2) EACH OF THE PARTIES UNDERSTANDS AND HAS CONSIDERED THE IMPLICATIONS OF THIS WAIVER, (3) EACH OF THE PARTIES MAKES THIS WAIVER VOLUNTARILY AND (4) EACH OF THE PARTIES HAS BEEN INDUCED TO ENTER INTO THIS AGREEMENT BY, AMONG OTHER THINGS, THE MUTUAL WAIVERS AND CERTIFICATIONS OF THIS SECTION 12. ANY PARTY MAY FILE AN ORIGINAL COUNTERPART OR A COPY OF THIS AGREEMENT WITH ANY COURT AS WRITTEN EVIDENCE OF THE CONSENT OF THE PARTIES TO THE WAIVER OF THEIR RIGHT TO TRIAL BY JURY.

13.    Waivers and Amendment. This Agreement may be changed, modified or amended, and the provisions and terms hereof may be waived, or the time for its performance extended, only by instrument in writing signed by each of the Parties hereto, or, in the case of a waiver, by the Party waiving compliance with such provision or term. Any change or modification to this Agreement shall be null and void, unless made by written amendment to this Agreement and signed by each of the Parties hereto. Any waiver of any provision or term of this Agreement, or any extension in time for performance of such provision or term, shall be validly and sufficiently authorized for the purposes of this Agreement if, as to any Party, it is authorized in writing by an authorized director or officer of such Party. No delay on the part of any Party in exercising any right, power or privilege hereunder shall operate as a waiver thereof, nor shall any single or partial exercise thereof preclude any other or further exercise thereof or the exercise of any other such right, power or privilege. No waiver of any breach of this Agreement shall be held to constitute a waiver of any preceding or subsequent breach.

14.    Counterparts. This Agreement may be executed in counterparts and such counterparts may be delivered in electronic format (including by e-signature or delivery of.pdf signature pages email) all of which shall be considered one and the same agreement and shall become effective when one or more counterparts have been signed by each Party and delivered to the other Party, it being understood that the Parties need not sign the same counterpart. Such delivery of counterparts shall be conclusive evidence of the intent to be bound hereby and each such counterpart and copies produced therefrom shall have the same effect as an original.

15.    Assignment. This Agreement and all of the provisions hereof will be binding upon and inure to the benefit of, and be enforceable by and against, the Parties to this Agreement and their respective successors and permitted assigns. Neither this Agreement nor any of the rights, interests or obligations hereunder may be assigned or delegated by any Party without the prior written consent of the other Party, and any attempted assignment without the prior written consent of the other Party shall be void and have no effect.