Skyward Specialty Insurance Group, Inc. Sample Contracts

CREDIT AGREEMENT dated as of March 29, 2023
Credit Agreement • April 3rd, 2023 • Skyward Specialty Insurance Group, Inc. • Fire, marine & casualty insurance • New York

This CREDIT AGREEMENT (this “Agreement”) is made and entered into as of March 29, 2023, by and among SKYWARD SPECIALTY INSURANCE GROUP, INC., a Delaware corporation (the “Borrower”), the several banks and other financial institutions and lenders from time to time party hereto (the “Lenders”) and TRUIST BANK, in its capacity as administrative agent for the Lenders (in such capacity, the “Administrative Agent”), as an Issuing Bank and as the Swingline Lender.

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shares of Common Stock SKYWARD SPECIALTY INSURANCE GROUP, INC. UNDERWRITING AGREEMENT
Underwriting Agreement • November 13th, 2023 • Skyward Specialty Insurance Group, Inc. • Fire, marine & casualty insurance • New York

Skyward Specialty Insurance Group, Inc., a Delaware corporation (the “Company”), and The Westaim Corporation, a stockholder of the Company, (the “Selling Stockholder”), propose to sell an aggregate of shares (the “Firm Stock”) of the Company’s common stock, par value $0.01 per share (the “Common Stock”). Of the shares of the Firm Stock, are being sold by the Company and are being sold by the Selling Stockholder. In addition, the Selling Stockholder proposes to grant to the underwriters named in Schedule I (the “Underwriters”) attached to this agreement (this “Agreement”) an option to purchase up to an aggregate of 675,000 additional shares of the Common Stock on the terms set forth in Section 3 (the “Option Stock”). The Firm Stock and the Option Stock, if purchased, are hereinafter collectively called the “Stock”. This Agreement is to confirm the agreement concerning the purchase of the Stock from the Company and the Selling Stockholder by the Underwriters.

SKYWARD SPECIALTY INSURANCE GROUP, INC. PERFORMANCE-BASED RESTRICTED STOCK UNITS AGREEMENT UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG- TERM INCENTIVE PLAN (COMBINED RATIO)
Restricted Stock Units Agreement • April 1st, 2024 • Skyward Specialty Insurance Group, Inc. • Fire, marine & casualty insurance • Delaware

This Notice evidences the award of performance-based restricted stock units (each, a “PSU,” and collectively, the “PSUs”) of Skyward Specialty Insurance Group, Inc., a Delaware corporation (the “Company”), that have been granted to you pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Long-Term Incentive Plan (the “Plan”) and conditioned upon your agreement to the terms of the attached Performance-Based Restricted Stock Units Agreement (the “Agreement”). This Notice constitutes part of and is subject to the terms and provisions of the Agreement and the Plan, which are incorporated by reference herein. Each PSU is equivalent in value to one share of the Company’s Common Stock and represents the Company’s commitment to issue one share of the Company’s Common Stock at a future date, subject to the terms of the Agreement and the Plan. The PSUs are credited to a separate account maintained for you on the books and records of the Company (the “Account”). All amounts credited to th

shares of Common Stock SKYWARD SPECIALTY INSURANCE GROUP, INC. UNDERWRITING AGREEMENT
Letter Agreement • January 4th, 2023 • Skyward Specialty Insurance Group, Inc. • Fire, marine & casualty insurance • New York

Barclays Capital Inc. Keefe, Bruyette & Woods, Inc., As Representatives of the several Underwriters named in Schedule I attached hereto,

SKYWARD SPECIALTY INSURANCE GROUP, INC. PERFORMANCE-BASED RESTRICTED STOCK UNITS AGREEMENT UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG- TERM INCENTIVE PLAN (Relative GBVPS)
Restricted Stock Units Agreement • March 28th, 2023 • Skyward Specialty Insurance Group, Inc. • Fire, marine & casualty insurance • Delaware

This Notice evidences the award of performance-based restricted stock units (each, an “PSU,” and collectively, the “PSUs”) of Skyward Specialty Insurance Group, Inc., a Delaware corporation (the “Company”), that have been granted to you pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Long-Term Incentive Plan (the “Plan”) and conditioned upon your agreement to the terms of the attached Performance-Based Restricted Stock Units Agreement (the “Agreement”). This Notice constitutes part of and is subject to the terms and provisions of the Agreement and the Plan, which are incorporated by reference herein. Each PSU is equivalent in value to one share of the Company’s Common Stock and represents the Company’s commitment to issue one share of the Company’s Common Stock at a future date, subject to the terms of the Agreement and the Plan. The PSUs are credited to a separate account maintained for you on the books and records of the Company (the “Account”). All amounts credited to t

Restricted Stock Agreement
Restricted Stock Agreement • January 12th, 2023 • Skyward Specialty Insurance Group, Inc. • Fire, marine & casualty insurance • Delaware

This Agreement (the “Agreement”) evidences the award of ____________ restricted shares (each, an “Award Share,” and collectively, the “Award Shares”) of the common stock of Skyward Specialty Insurance Group, Inc., a Delaware corporation (the “Company”), granted to you, _______________________, effective as of ____________ (the “Grant Date”), pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Long-Term Incentive Plan (the “Plan”) and conditioned upon your agreement to the terms described below. All of the provisions of the Plan are expressly incorporated into this Agreement.

FIRST AMENDMENT
First Amendment • April 1st, 2024 • Skyward Specialty Insurance Group, Inc. • Fire, marine & casualty insurance • New York

THIS FIRST AMENDMENT, dated as of February 26, 2024 (this “Agreement”), is by and among SKYWARD SPECIALTY INSURANCE GROUP, INC., a Delaware corporation (the “Borrower”), the Lenders party hereto (which, for the avoidance of doubt, constitute the Required Lenders), and TRUIST BANK, in its capacities as administrative agent for the Lenders (in such capacity, the “Administrative Agent”) and as a Lender.

SKYWARD SPECIALTY INSURANCE GROUP, INC. PERFORMANCE UNIT AGREEMENT UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN (COMBINED RATIO)
Performance Unit Agreement • April 1st, 2024 • Skyward Specialty Insurance Group, Inc. • Fire, marine & casualty insurance • Delaware

This Notice evidences the award of cash-settled performance stock units (each, a “PU,” and collectively, the “PUs”) of Skyward Specialty Insurance Group, Inc., a Delaware corporation (the “Company”), that have been granted to you pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Long-Term Incentive Plan (the “Plan”) and conditioned upon your agreement to the terms of the attached Performance Unit Agreement (the “Agreement”). This Notice constitutes part of and is subject to the terms and provisions of the Agreement and the Plan, which are incorporated by reference herein. Each PU is equivalent in value to the dollar value provided for in this Notice, subject to the terms of the Agreement and the Plan. The PUs are credited to a separate account maintained for you on the books and records of the Company (the “Account”). All amounts credited to the Account will continue for all purposes to be part of the general assets of the Company.

SKYWARD SPECIALTY INSURANCE GROUP, INC. PERFORMANCE UNIT AGREEMENT UNDER THE SKYWARD SPECIALTY INSURANCE GROUP, INC. 2022 LONG-TERM INCENTIVE PLAN (COMBINED RATIO)
Performance Unit Agreement • March 28th, 2023 • Skyward Specialty Insurance Group, Inc. • Fire, marine & casualty insurance • Delaware

This Notice evidences the award of cash-settled performance stock units (each, an “PU,” and collectively, the “PUs”) of Skyward Specialty Insurance Group, Inc., a Delaware corporation (the “Company”), that have been granted to you pursuant to the Skyward Specialty Insurance Group, Inc. 2022 Long-Term Incentive Plan (the “Plan”) and conditioned upon your agreement to the terms of the attached Performance Unit Agreement (the “Agreement”). This Notice constitutes part of and is subject to the terms and provisions of the Agreement and the Plan, which are incorporated by reference herein. Each PU is equivalent in value to the dollar value provided for in this Notice, subject to the terms of the Agreement and the Plan. The PUs are credited to a separate account maintained for you on the books and records of the Company (the “Account”). All amounts credited to the Account will continue for all purposes to be part of the general assets of the Company.

SECOND AMENDMENT AGREEMENT TO THE INVESTMENT MANAGEMENT AGREEMENT
Investment Management Agreement • April 1st, 2024 • Skyward Specialty Insurance Group, Inc. • Fire, marine & casualty insurance • New York

THIS SECOND AMENDMENT AGREEMENT TO THE INVESTMENT MANAGEMENT AGREEMENT (the “Second Amendment Agreement”) is entered into this December 8, 2023, with an effective date as of December 8, 2023, between Houston Specialty Insurance Company, Imperium Insurance Company and Great Midwest Insurance Company (collectively the “Client”) and Arena Investors, LP, a Delaware limited partnership, as investment manager (the “Investment Adviser”). The Client and the Investment Adviser are sometimes each individually referred to as a “Party” and collectively as the “Parties”. Any terms used but not defined herein have the meanings assigned to them in the IMA (as defined below).

GUARANTY AGREEMENT
Assumption Agreement • April 3rd, 2023 • Skyward Specialty Insurance Group, Inc. • Fire, marine & casualty insurance • New York

This GUARANTY AGREEMENT, dated as of March 29, 2023, is made by SKYWARD SERVICE COMPANY, a Delaware corporation (“Skyward Service”) and SKYWARD UNDERWRITERS AGENCY, INC., a Texas corporation (“Skyward Underwriters”; and together with Skyward Service and any Person who becomes a “Guarantor” pursuant to the terms hereof after the date hereof, collectively, the “Guarantors” and each, individually, a “Guarantor”) in favor of TRUIST BANK, as administrative agent (in such capacity, together with its successors in such capacity, the “Administrative Agent”) for the Lenders.

4,400,000 shares of Common Stock SKYWARD SPECIALTY INSURANCE GROUP, INC. UNDERWRITING AGREEMENT
Underwriting Agreement • May 7th, 2024 • Skyward Specialty Insurance Group, Inc. • Fire, marine & casualty insurance • New York

Westaim HIIG GP Inc. (the “Selling Stockholder”), a stockholder of Skyward Specialty Insurance Group, Inc., a Delaware corporation (the “Company”), proposes to sell an aggregate of 4,400,000 shares (the “Firm Stock”) of the Company’s common stock, par value $0.01 per share (the “Common Stock”). In addition, the Selling Stockholder proposes to grant to the underwriters named in Schedule I (the “Underwriters”) attached to this agreement (this “Agreement”) an option to purchase up to an aggregate of 660,000 additional shares of the Common Stock on the terms set forth in Section 3 (the “Option Stock”). The Firm Stock and the Option Stock, if purchased, are hereinafter collectively called the “Stock”. This Agreement is to confirm the agreement concerning the purchase of the Stock from the Selling Stockholder by the Underwriters.

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