0001628280-24-022759 Sample Contracts

Bowhead Specialty Holdings Inc. [•] Shares of Common Stock, par value $0.01 per share Underwriting Agreement
Underwriting Agreement • May 13th, 2024 • Bowhead Specialty Holdings Inc. • 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”.

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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”).

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”).

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.

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

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.

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”).

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”).

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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