0001628279-20-000238 Sample Contracts

FIFTH AMENDED AND RESTATED INVESTORS’ RIGHTS AGREEMENT
Investors’ Rights Agreement • September 17th, 2020 • Root Stockholdings, Inc. • Fire, marine & casualty insurance • Delaware

THIS FIFTH AMENDED AND RESTATED INVESTORS’ RIGHTS AGREEMENT (this “Agreement”), is made as of the 25th day of November, 2019, by and among Root Stockholdings, Inc., a Delaware corporation (the “Company”), each of the Investors listed on Schedule A hereto, each of which is referred to in this Agreement as an “Investor” and any holder of a Lender Warrant (as defined below) that becomes a party to this Agreement in accordance with Section 6.15 hereof.

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Contract
Purchase Stock • September 17th, 2020 • Root Stockholdings, Inc. • Fire, marine & casualty insurance • California

THIS WARRANT AND THE SHARES ISSUABLE HEREUNDER HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “ACT”), OR THE SECURITIES LAWS OF ANY STATE AND, EXCEPT AS SET FORTH IN SECTIONS 5.3 AND 5.4 BELOW, MAY NOT BE OFFERED, SOLD, PLEDGED OR OTHERWISE TRANSFERRED UNLESS AND UNTIL REGISTERED UNDER SAID ACT AND LAWS OR IN FORM AND SUBSTANCE SATISFACTORY TO THE COMPANY, SUCH OFFER, SALE, PLEDGE OR OTHER TRANSFER IS EXEMPT FROM SUCH REGISTRATION.

AMENDED AND RESTATED TERM LOAN AGREEMENT dated as of November 25, 2019 by and among ROOT, INC.
Term Loan Agreement • September 17th, 2020 • Root Stockholdings, Inc. • Fire, marine & casualty insurance • New York

THIS AMENDED AND RESTATED TERM LOAN AGREEMENT (this “Agreement”) is made and entered into as of November 25, 2019, by and among ROOT STOCKHOLDINGS, INC., a Delaware corporation (“Holdings”), ROOT, INC., a Delaware corporation (the “Borrower”), the several banks and other financial institutions and lenders from time to time party hereto (the “Lenders”), and SUNTRUST BANK, in its capacity as Administrative Agent for the Lenders.

ROOT, INC. RESTRICTED STOCK UNIT AGREEMENT
Restricted Stock Unit Agreement • September 17th, 2020 • Root Stockholdings, Inc. • Fire, marine & casualty insurance • Ohio
LOAN AND SECURITY AGREEMENT
Loan and Security Agreement • September 17th, 2020 • Root Stockholdings, Inc. • Fire, marine & casualty insurance

THIS LOAN AND SECURITY AGREEMENT (this “Agreement”) dated as of July 7 , 2016 (the “Effective Date”) between SILICON VALLEY BANK (“Bank”), and IBOD COMPANY, INC. (“Borrower”), provides the terms on which Bank shall lend to Borrower and Borrower shall repay Bank. The parties agree as follows:

NOTE PURCHASE AGREEMENT dated as of November 25, 2019 by and among ROOT STOCKHOLDINGS, INC. as Holdings ROOT, INC. as Issuer THE NOTEHOLDERS FROM TIME TO TIME PARTY HERETO and WILMINGTON TRUST, NATIONAL ASSOCIATION as Administrative Agent
Note Purchase Agreement • September 17th, 2020 • Root Stockholdings, Inc. • Fire, marine & casualty insurance • New York

THIS NOTE PURCHASE AGREEMENT (this “Agreement”) is made and entered into as of November 25, 2019, by and among ROOT STOCKHOLDINGS, INC., a Delaware corporation (“Holdings”), ROOT, INC., a Delaware corporation (the “Issuer”), the NOTEHOLDERS from time to time party hereto (the “Noteholders”) and WILMINGTON TRUST, NATIONAL ASSOCIATION (“Wilmington Trust”), in its capacity as Administrative Agent for the Noteholders.

ROOT, INC. STOCK OPTION AGREEMENT
Equity Incentive Plan • September 17th, 2020 • Root Stockholdings, Inc. • Fire, marine & casualty insurance • Delaware

Root, Inc., a Delaware corporation, (the “Company”), hereby grants to the Participant an option under the Plan to purchase the number of shares of the Company’s Common Stock indicated in the notice of stock option grant delivered physically or electronically by the Company (the “Grant Notice”) at the exercise price indicated in the Grant Notice.

OFFICE LEASE AGREEMENT BETWEEN TWO25 COMMONS LLC (Landlord) AND IBOD COMPANY, INC. (Tenant)
Office Lease Agreement • September 17th, 2020 • Root Stockholdings, Inc. • Fire, marine & casualty insurance • Ohio
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