Skyward Specialty Insurance Group, Inc. Sample Contracts
CREDIT AGREEMENT dated as of March 29, 2023Credit 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.
4,400,000 shares of Common Stock SKYWARD SPECIALTY INSURANCE GROUP, INC. UNDERWRITING AGREEMENTUnderwriting 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.
ADVANCES AND SECURITY AGREEMENTAdvances and Security Agreement • September 9th, 2024 • Skyward Specialty Insurance Group, Inc. • Fire, marine & casualty insurance • Texas
This Advances and Security Agreement (“Agreement”) is made as of August 1st, 2023 , between the Federal Home Loan Bank of Dallas (“Bank”), with its principal office located at 8500 Freeport Parkway South, Suite 600, Irving, Texas 75063, mailing address: P.O. Box 619026, Dallas, Texas 75261-9026 and Houston Specialty Insurance Company a Insurance Company (“Borrower”), with its chief executive office located at
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)Performance-Based Restricted Stock Units Agreement • March 5th, 2025 • 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
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)Performance-Based 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
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)Performance-Based 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
CERTAIN INFORMATION HAS BEEN EXCLUDED FROM THIS AGREEMENT (INDICATED BY [***]) BECAUSE SUCH INFORMATION IS BOTH NOT MATERIAL AND OF THE TYPE THAT THE REGISTRANT TREATS AS PRIVATE OR CONFIDENTIAL.Share Purchase Agreement • September 8th, 2025 • Skyward Specialty Insurance Group, Inc. • Fire, marine & casualty insurance
DATED 2 SEPTEMBER 2025 ASO VICTORIA 4 S.À R.L.andMETACOMET LLCandHOWDEN APOLLO LIMITEDandSKYWARD SPECIALTY INSURANCE GROUP, INC.andAPOLLO GROUP HOLDINGS LIMITED AGREEMENT for the sale and purchase of shares in Apollo Group Holdings Limited
Restricted Stock AgreementRestricted 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 AMENDMENTCredit Agreement • 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.
CREDIT AGREEMENT DATED AS OF NOVEMBER 13, 2025 AMONG SKYWARD SPECIALTY INSURANCE GROUP, INC., AS THE BORROWER THE LENDERS FROM TIME TO TIME PARTY HERETO AND BARCLAYS BANK PLC, AS ADMINISTRATIVE AGENT AND BARCLAYS BANK PLC, TRUIST SECURITIES, INC.,...Credit Agreement • November 18th, 2025 • Skyward Specialty Insurance Group, Inc. • Fire, marine & casualty insurance • New York
FIRST AMENDMENTFirst Amendment • January 6th, 2026 • Skyward Specialty Insurance Group, Inc. • Fire, marine & casualty insurance • New York
This CREDIT AGREEMENT (this “Agreement”) is made and entered into as of November 13, 2025, 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 BARCLAYS BANK PLC, in its capacity as administrative agent for the Lenders (in such capacity, the “Administrative Agent”), as an Issuing Bank and as the Swingline Lender.
GUARANTY AGREEMENTGuaranty Agreement • November 18th, 2025 • Skyward Specialty Insurance Group, Inc. • Fire, marine & casualty insurance • New York
This GUARANTY AGREEMENT, dated as of November 13, 2025, 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 BARCLAYS BANK PLC, as administrative agent (in such capacity, together with its successors in such capacity, the “Administrative Agent”) for the Lenders (as defined below).
SECOND AMENDMENT TO EMPLOYMENT AGREEMENTEmployment Agreement • March 3rd, 2025 • Skyward Specialty Insurance Group, Inc. • Fire, marine & casualty insurance
This SECOND AMENDMENT TO EMPLOYMENT AGREEMENT (“First Amendment”) is effective as of the 1st day of March, 2025 by and among SKYWARD SPECIALTY INSURANCE GROUP, INC., SKYWARD SERVICE COMPANY, (together “Company’), and ANDREW ROBINSON, (“Executive”).
FORM OF EXECUTIVE EMPLOYMENT AGREEMENTExecutive Employment Agreement • May 11th, 2026 • Skyward Specialty Insurance Group, Inc. • Fire, marine & casualty insurance • Texas
This EMPLOYMENT AGREEMENT (the “Agreement”) is entered into and effective as of [___________] (the “Effective Date”) by and between Skyward Specialty Insurance Group, Inc. (the “Company”), and [___________________] (“Executive”). Each of the Company and Executive are a “Party,” and collectively, they are the “Parties.”
Severance Agreement For [_________] (“Employee”)Severance Agreement • March 3rd, 2025 • Skyward Specialty Insurance Group, Inc. • Fire, marine & casualty insurance
If Skyward Service Company (the “Company”) terminates Employee’s employment without cause or Employee terminates his/her employment for “Good Reason,” the Company will pay the Employee an amount equal to twelve (12) months of Employee’s base salary, following the termination date, payable in roughly equal installments in accordance with the Company’s normal payroll practices, the first installment of which shall be paid upon the execution of a release and waiver by the Employee, the timing of such payment to be adjusted as necessary to conform with 409A requirements. The Company will also provide Employee with health insurance benefits during for twelve (12) months following the termination date through the payment of Employee’s then applicable COBRA premiums (the payments in this paragraph collective the “Severance Payments”). For purposes of this Agreement, “Good Reason” shall mean:
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 AGREEMENTInvestment 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).
TERM LOAN CREDIT AGREEMENT DATED AS OF DECEMBER 30, 2025 AMONG SKYWARD SPECIALTY INSURANCE GROUP, INC., AS THE BORROWER THE LENDERS FROM TIME TO TIME PARTY HERETO AND BARCLAYS BANK PLC, AS ADMINISTRATIVE AGENT BARCLAYS BANK PLC as Sole Lead Arranger...Term Loan Credit Agreement • January 6th, 2026 • Skyward Specialty Insurance Group, Inc. • Fire, marine & casualty insurance • New York
This TERM LOAN CREDIT AGREEMENT (this “Agreement”) is made and entered into as of December 30, 2025, 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 BARCLAYS BANK PLC, in its capacity as administrative agent for the Lenders (in such capacity, together with any successor administrative agent, the “Administrative Agent”).
COMMUTATION AND RELEASE AGREEMENTCommutation and Release Agreement • February 5th, 2025 • Skyward Specialty Insurance Group, Inc. • Fire, marine & casualty insurance • Texas
(3)Houston Specialty Insurance Company, Imperium Insurance Company, and Great Midwest Insurance Company, (each a “Ceding Company,” and collectively, the “Ceding Companies”),
GUARANTY AGREEMENTGuaranty Agreement • January 6th, 2026 • Skyward Specialty Insurance Group, Inc. • Fire, marine & casualty insurance • New York
This GUARANTY AGREEMENT, dated as of December 30, 2025, 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 BARCLAYS BANK PLC, as administrative agent (in such capacity, together with its successors in such capacity, the “Administrative Agent”) for the Lenders (as defined below).
GUARANTY AGREEMENTGuaranty 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.