Bowhead Specialty Holdings Inc. Sample Contracts

CREDIT AGREEMENT dated as of April 22, 2024 among BOWHEAD SPECIALTY HOLDINGS INC. The Lenders Party Hereto JPMORGAN CHASE BANK, N.A. as Administrative Agent, Issuing Bank and Swingline Lender and MORGAN STANLEY SENIOR FUNDING, INC. as Syndication...
Credit Agreement • May 3rd, 2024 • Bowhead Specialty Holdings Inc. • Fire, marine & casualty insurance • New York

CREDIT AGREEMENT, dated as of April 22, 2024 (this “Agreement”), among BOWHEAD SPECIALTY HOLDINGS INC., the LENDERS from time to time party hereto and JPMORGAN CHASE BANK, N.A., as Administrative Agent, Issuing Bank and Swingline Lender.

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Bowhead Specialty Holdings Inc. [•] Shares of Common Stock, par value $0.01 per share Underwriting Agreement
Bowhead Specialty Holdings Inc. • May 13th, 2024 • Fire, marine & casualty insurance • New York

Bowhead Specialty Holdings Inc., a Delaware corporation (the “Company”), proposes to issue and sell to the several underwriters listed in Schedule 1 hereto (the “Underwriters”), for whom you are acting as representatives (the “Representatives”), an aggregate of [•] shares of common stock, par value $0.01 per share (“Common Stock”), of the Company (the “Underwritten Shares”) and, at the option of the Underwriters, up to an additional [•] shares of Common Stock of the Company (the “Option Shares”). The Underwritten Shares and the Option Shares are herein referred to as the “Shares”. The shares of Common Stock of the Company to be outstanding after giving effect to the sale of the Shares are referred to herein as the “Stock”.

Managing General Agency Agreement between Homesite Insurance Company and Bowhead Specialty Underwriters, Inc. Dated as of February 1, 2021
Managing General Agency Agreement • May 3rd, 2024 • Bowhead Specialty Holdings Inc. • Fire, marine & casualty insurance
INSURANCE TRUST AGREEMENT
Insurance Trust Agreement • May 3rd, 2024 • Bowhead Specialty Holdings Inc. • Fire, marine & casualty insurance

This Insurance Trust Agreement (the “Agreement”) is among Bowhead Insurance Company, Inc., a corporation organized under the laws of Wisconsin (the “Grantor”), American Family Mutual Insurance Company, S.I., a corporation organized under the laws of Wisconsin (the “Beneficiary”), and U.S. Bank National Association, as trustee (the “Bank”); and

Bowhead Specialty Holdings Inc. [4,000,000] Shares of Common Stock, par value $0.01 per share Underwriting Agreement
Bowhead Specialty Holdings Inc. • October 21st, 2024 • Fire, marine & casualty insurance • New York

Certain stockholders named in Schedule 2 hereto (the “Selling Stockholders”) of Bowhead Specialty Holdings Inc., a Delaware corporation (the “Company”), propose, severally and not jointly, to sell to the several underwriters listed in Schedule 1 hereto (the “Underwriters”), for whom you are acting as representatives (the “Representatives”), an aggregate of [4,000,000] shares of common stock, par value $0.01 per share (“Common Stock”), of the Company (the “Underwritten Shares”) and, at the option of the Underwriters, up to an additional [600,000] shares of Common Stock of the Company (the “Option Shares”). The Underwritten Shares and the Option Shares are herein referred to as the “Shares”. The shares of Common Stock of the Company to be outstanding after giving effect to the sale of the Shares are referred to herein as the “Stock.”

EMPLOYMENT AGREEMENT
Employment Agreement • May 13th, 2024 • Bowhead Specialty Holdings Inc. • Fire, marine & casualty insurance • New York

This AGREEMENT (this “Agreement”) is made as of May _____, 2024, to be effective as of the closing date of the Company’s initial public offering or, if earlier, a Change in Control (as defined below) (the “Effective Date”), by and between Bowhead Specialty Holdings Inc. (the “Company”), and Stephen J. Sills (the “Executive”) (collectively, the “Parties”).

QUOTA SHARE REINSURANCE AGREEMENT
Reinsurance Agreement • May 3rd, 2024 • Bowhead Specialty Holdings Inc. • Fire, marine & casualty insurance

THIS QUOTA SHARE REINSURANCE AGREEMENT (this “Agreement”) is made and entered into as of the 1st day of January, 2021 with effect as at 12:01 a.m. Eastern Standard Time, on November 1, 2020 (the “Effective Date”), by and between American Family Mutual Insurance Company, S.I. (the “Company”) and Bowhead Insurance Company, Inc. (the “Reinsurer”);

FORM OF BOARD NOMINEE AGREEMENT
Board Nominee Agreement • May 13th, 2024 • Bowhead Specialty Holdings Inc. • Fire, marine & casualty insurance • Delaware

This BOARD NOMINEE AGREEMENT (this “Agreement”), dated as of [l], 2024, is entered into by and between Bowhead Specialty Holdings Inc., a Delaware corporation (the “Company”), and GPC Partners Investments (SPV III) LP, a Delaware limited partnership (“GP”) (the Company and GP, each a “Party” and together, the “Parties”). Capitalized terms used herein shall have the meanings set forth in Section 2 of this Agreement.

COMMON STOCK PURCHASE WARRANT BOWHEAD SPECIALTY HOLDINGS INC.
Common Stock Purchase Warrant • August 8th, 2024 • Bowhead Specialty Holdings Inc. • Fire, marine & casualty insurance • Delaware

This COMMON STOCK PURCHASE WARRANT (this “Warrant”) certifies that, for value received, American Family Mutual Insurance Company, S.I., a Wisconsin corporation (the “Holder”), is entitled, upon the terms and subject to the limitations on exercise and the conditions hereinafter set forth, to purchase from Bowhead Specialty Holdings Inc., a Delaware corporation (the “Company”), (i) up to 1,614,250 shares of Common Stock (as defined below) and (ii) if applicable, up to 56,471 additional shares of Common Stock to the extent the underwriters’ overallotment option in the initial public offering of the Company (the “Over-allotment Option”) is exercised (subject to any adjustments pursuant to Section 3 hereof, clauses (i) and (ii) collectively, the “Warrant Shares”), which represent the number of shares of Common Stock that would constitute five percent (5%) of all issued and outstanding shares of Common Stock on a Fully Diluted basis as of the Issuance Date or, if applicable, the date of the

REGISTRATION RIGHTS AGREEMENT
Registration Rights Agreement • August 8th, 2024 • Bowhead Specialty Holdings Inc. • Fire, marine & casualty insurance • New York

THIS REGISTRATION RIGHTS AGREEMENT (this “Agreement”) is entered into as of this 28th day of May, 2024 among Bowhead Specialty Holdings Inc., a Delaware corporation (the “Company”), the persons listed on Schedule A hereto and any person who becomes a party hereto pursuant to Section 7(e) (such persons collectively, in their capacities as holders of Registrable Securities (as defined below), the “Holders” and each a “Holder”, including (i) GPC Fund (as defined below) and (ii) AFMIC (as defined below) and, together with GPC Fund, the “Institutional Holders”).

EMPLOYMENT AGREEMENT
Employment Agreement • August 8th, 2024 • Bowhead Specialty Holdings Inc. • Fire, marine & casualty insurance • New York

This AGREEMENT (this “Agreement”) is made as of May 22, 2024, to be effective as of the closing date of the Company’s initial public offering or, if earlier, a Change in Control (as defined below) (the “Effective Date”), by and between Bowhead Specialty Holdings Inc. (the “Company”), and Stephen J. Sills (the “Executive”) (collectively, the “Parties”).

FORM OF INVESTOR MATTERS AGREEMENT
Investor Matters Agreement • May 13th, 2024 • Bowhead Specialty Holdings Inc. • Fire, marine & casualty insurance • Delaware

THIS INVESTOR MATTERS AGREEMENT (this “Agreement”) dated as of [l], 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.

FORM OF COMMON STOCK PURCHASE WARRANT BOWHEAD SPECIALTY HOLDINGS INC.
Common Stock Purchase Warrant • May 13th, 2024 • Bowhead Specialty Holdings Inc. • Fire, marine & casualty insurance • Delaware

This COMMON STOCK PURCHASE WARRANT (this “Warrant”) certifies that, for value received, American Family Mutual Insurance Company, S.I., a Wisconsin corporation (the “Holder”), is entitled, upon the terms and subject to the limitations on exercise and the conditions hereinafter set forth, to purchase from Bowhead Specialty Holdings Inc., a Delaware corporation (the “Company”), (i) up to 1,576,667 shares of Common Stock (as defined below) and (ii) if applicable, up to 50,000 additional shares of Common Stock to the extent the underwriters’ overallotment option in the initial public offering of the Company (the “Over-allotment Option”) is exercised (subject to any adjustments pursuant to Section 3 hereof, clauses (i) and (ii) collectively, the “Warrant Shares”), which represent the number of shares of Common Stock that would constitute five percent (5%) of all issued and outstanding shares of Common Stock on a Fully Diluted basis as of the Issuance Date or, if applicable, the date of the

AMENDED AND RESTATED QUOTA SHARE REINSURANCE AGREEMENT
Quota Share Reinsurance Agreement • August 8th, 2024 • Bowhead Specialty Holdings Inc. • Fire, marine & casualty insurance

THIS AMENDED AND RESTATED QUOTA SHARE REINSURANCE AGREEMENT (this “Agreement”) is made and entered into as of the 23rd day of May, 2024 (the “Date of Determination”) with effect as at 12:01 a.m. Eastern Standard Time, on November 1, 2020 (the “Effective Date”), by and between American Family Mutual Insurance Company, S.I. (the “Company”) and Bowhead Insurance Company, Inc. (the “Reinsurer”);

AMENDED AND RESTATED QUOTA SHARE REINSURANCE AGREEMENT
Quota Share Reinsurance Agreement • May 3rd, 2024 • Bowhead Specialty Holdings Inc. • Fire, marine & casualty insurance

THIS AMENDED AND RESTATED QUOTA SHARE REINSURANCE AGREEMENT (this “Agreement”) is made and entered into as of the __ day of [ ], 2024 (the “Date of Determination”) with effect as at 12:01 a.m. Eastern Standard Time, on November 1, 2020 (the “Effective Date”), by and between American Family Mutual Insurance Company, S.I. (the “Company”) and Bowhead Insurance Company, Inc. (the “Reinsurer”);

INVESTOR MATTERS AGREEMENT
Investor Matters Agreement • August 8th, 2024 • Bowhead Specialty Holdings Inc. • Fire, marine & casualty insurance • Delaware

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.

SERVICES AGREEMENT
Services Agreement • May 3rd, 2024 • Bowhead Specialty Holdings Inc. • Fire, marine & casualty insurance • Wisconsin

This Services Agreement (“Agreement”) is entered into as of October 7, 2020, by and among Bowhead Insurance Holdings LP, a Delaware limited partnership (“Bowhead Insurance Holdings”) Bowhead Specialty Underwriters, Inc., a Delaware corporation (“Bowhead Specialty”), Bowhead Underwriting Services, Inc., a Delaware corporation (“Bowhead Services”), Bowhead Insurance Company, Inc., a Wisconsin insurance company (“Bowhead Insurance”), and each of their affiliates, which after the date hereof may be identified as the other signatories in a Joinder Agreement hereto. All of the foregoing are herein referred to individually as a “Party” and collectively as the “Parties.”

AMENDED AND RESTATED LIMITED PARTNERSHIP AGREEMENT OF BOWHEAD INSURANCE HOLDINGS LP A DELAWARE LIMITED PARTNERSHIP
Limited Partnership Agreement • May 3rd, 2024 • Bowhead Specialty Holdings Inc. • Fire, marine & casualty insurance • Delaware

THIS AMENDED AND RESTATED LIMITED PARTNERSHIP AGREEMENT of BOWHEAD INSURANCE HOLDINGS LP, a Delaware limited partnership (the “Partnership”), is entered into, and shall be effective as of, October 14, 2020 (the “Effective Date”), by and among the current Partners (as defined below) and all other Persons (as defined below) bound hereby. ARTICLE I contains definitions of certain terms used in this Agreement. By its signature below, each of the Partners hereby acknowledges and agrees that this Agreement supersedes, amends and restates in its entirety the Limited Partnership Agreement of Bowhead Insurance Holdings LP, dated as of September 14, 2020 (as amended and in effect immediately prior to the effectiveness of this Agreement, the “Prior Agreement”).

BOARD NOMINEE AGREEMENT
Board Nominee Agreement • August 8th, 2024 • Bowhead Specialty Holdings Inc. • Fire, marine & casualty insurance • Delaware

This BOARD NOMINEE AGREEMENT (this “Agreement”), dated as of May 23, 2024, is entered into by and between Bowhead Specialty Holdings Inc., a Delaware corporation (the “Company”), and GPC Partners Investments (SPV III) LP, a Delaware limited partnership (“GP”) (the Company and GP, each a “Party” and together, the “Parties”). Capitalized terms used herein shall have the meanings set forth in Section 2 of this Agreement.

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INDEMNIFICATION AGREEMENT
Indemnification Agreement • May 13th, 2024 • Bowhead Specialty Holdings Inc. • Fire, marine & casualty insurance • Delaware

This INDEMNIFICATION AGREEMENT (this “Agreement”) is made and effective as of , 20 , by and between Bowhead Specialty Holdings Inc., a Delaware corporation (the “Company”), and [•] (“Indemnitee”).

AMENDED AND RESTATED INSURANCE TRUST AGREEMENT
Insurance Trust Agreement • August 8th, 2024 • Bowhead Specialty Holdings Inc. • Fire, marine & casualty insurance

This Amended and Restated Insurance Trust Agreement (the “Agreement”) is among Bowhead Insurance Company, Inc., a corporation organized under the laws of Wisconsin (the “Grantor”), American Family Mutual Insurance Company, S.I., a corporation organized under the laws of Wisconsin (the “Beneficiary”), and U.S. Bank National Association, as trustee (the “Bank”); and

REGISTRATION RIGHTS AGREEMENT
Registration Rights Agreement • May 13th, 2024 • Bowhead Specialty Holdings Inc. • Fire, marine & casualty insurance • New York

THIS REGISTRATION RIGHTS AGREEMENT (this “Agreement”) is entered into as of this [●] day of [●], 2024 among Bowhead Specialty Holdings Inc., a Delaware corporation (the “Company”), the persons listed on Schedule A hereto and any person who becomes a party hereto pursuant to Section 7(e) (such persons collectively, in their capacities as holders of Registrable Securities (as defined below), the “Holders” and each a “Holder”, including (i) GPC Fund (as defined below) and (ii) AFMIC (as defined below) and, together with GPC Fund, the “Institutional Holders”).

BOWHEAD SPECIALTY HOLDINGS INC.
Restricted Stock Unit Award Agreement • May 13th, 2024 • Bowhead Specialty Holdings Inc. • Fire, marine & casualty insurance • Delaware

This Restricted Stock Unit Award Agreement (this “Award Agreement”), dated as of __________, ____ (the “Date of Grant”), is made by and between Bowhead Specialty Holdings Inc., a Delaware corporation (the “Company”), and _________ (the “Participant”). Capitalized terms used but not defined herein shall have the meaning ascribed to them in the Bowhead Specialty Holdings Inc. 2024 Omnibus Incentive Plan (as may be amended from time to time, the “Plan”).

AMENDED AND RESTATED MANAGING GENERAL AGENCY AGREEMENT
Managing General Agency Agreement • August 8th, 2024 • Bowhead Specialty Holdings Inc. • Fire, marine & casualty insurance

This Amended and Restated Managing General Agency Agreement (this “Agreement”), dated as of May 23, 2024, is made and entered into by and between Homesite Insurance Company, a Wisconsin corporation (the “Company”), and Bowhead Specialty Underwriters, Inc., a Delaware corporation (the “Managing General Agent”).

AMENDMENT TO SERVICES AGREEMENT
Services Agreement • May 3rd, 2024 • Bowhead Specialty Holdings Inc. • Fire, marine & casualty insurance • New York

THIS AMENDMENT dated as of May 2, 2024 (this “Amendment”), to the Services Agreement dated as of October 7, 2020 (“Agreement”), is by and among Bowhead Insurance Holdings LP, a Delaware limited partnership, Bowhead Specialty Underwriters, Inc., a Delaware corporation, Bowhead Underwriting Services, Inc., a Delaware corporation, Bowhead Insurance Company, Inc., a Wisconsin insurance company, and Bowhead Specialty Holdings Inc a Delaware corporation. All of the foregoing are herein referred to individually as a “Party” and collectively as the “Parties.”

SECOND AMENDMENT TO THE AMENDED AND RESTATED LIMITED PARTNERSHIP AGREEMENT OF BOWHEAD INSURANCE HOLDINGS LP
Limited Partnership Agreement • May 3rd, 2024 • Bowhead Specialty Holdings Inc. • Fire, marine & casualty insurance

This Second Amendment (this “Amendment”) to the Amended and Restated Limited Partnership Agreement of Bowhead Insurance Holdings LP, a Delaware limited partnership (the “Partnership”), is made and entered into effective as of January 29, 2024 (the “Amendment Effective Date”), by and among the Partnership and the Requisite Partners (as defined below). Capitalized terms used but not otherwise defined herein have the meanings set forth in the Partnership Agreement.

FIRST AMENDMENT TO THE AMENDED AND RESTATED LIMITED PARTNERSHIP AGREEMENT OF BOWHEAD INSURANCE HOLDINGS LP
Limited Partnership Agreement • May 3rd, 2024 • Bowhead Specialty Holdings Inc. • Fire, marine & casualty insurance

This First Amendment (this “Amendment”) to the Amended and Restated Limited Partnership Agreement of Bowhead Insurance Holdings LP, a Delaware limited partnership (the “Partnership”), is made and entered into effective as of December 15, 2023 (the “Amendment Effective Date”), by and among the Partnership and the Requisite Partners (as defined below). Capitalized terms used but not otherwise defined herein have the meanings set forth in the Partnership Agreement.

JOINDER TO SERVICES AGREEMENT
Joinder to Services Agreement • May 3rd, 2024 • Bowhead Specialty Holdings Inc. • Fire, marine & casualty insurance • New York

THIS JOINDER AGREEMENT (the “Joinder”) is executed as of May 2, 2024 by and among Bowhead Insurance Holdings LP, a Delaware limited partnership, Bowhead Specialty Underwriters, Inc., a Delaware corporation, Bowhead Underwriting Services Inc., a Delaware corporation, Bowhead Insurance Company, Inc., a Wisconsin stock insurance company, and Bowhead Specialty Holdings Inc., a Delaware corporation, and is effective as of the date hereof.

BOWHEAD SPECIALTY HOLDINGS INC.
Restricted Stock Unit Award Agreement • May 13th, 2024 • Bowhead Specialty Holdings Inc. • Fire, marine & casualty insurance • Delaware

This Restricted Stock Unit Award Agreement (this “Award Agreement”), dated as of __________, ____ (the “Date of Grant”), is made by and between Bowhead Specialty Holdings Inc., a Delaware corporation (the “Company”), and _________ (the “Participant”). Capitalized terms used but not defined herein shall have the meaning ascribed to them in the Bowhead Specialty Holdings Inc. 2024 Omnibus Incentive Plan (as may be amended from time to time, the “Plan”).

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