Root, Inc. Sample Contracts

INDEMNIFICATION AGREEMENT
Indemnification Agreement • February 23rd, 2022 • Root, Inc. • Fire, marine & casualty insurance • Delaware

THIS INDEMNIFCATION AGREEMENT (the “Agreement”) is made and entered into as of [Effective Date] between Root, Inc., a Delaware corporation (the “Company”), and [Name of Director] (“Indemnitee”).

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Root, Inc. Class A Common Stock, par value $0.0001 per share Underwriting Agreement
Underwriting Agreement • October 26th, 2020 • Root, Inc. • Fire, marine & casualty insurance • New York

Root, Inc., a Delaware corporation (the “Company”), proposes, subject to the terms and conditions stated in this agreement (this “Agreement”), to issue and sell to the Underwriters named in Schedule I hereto (the “Underwriters”) an aggregate of [___] shares and, at the election of the Underwriters, up to [___] additional shares of Class A Common Stock, par value $0.0001 per share (“Stock”) of the Company, and each of the selling stockholders of the Company named in Schedule II hereto (the “Selling Stockholders”) proposes, subject to the terms and conditions stated in this Agreement, to sell to the Underwriters an aggregate of [___] shares of Stock. The aggregate of [___] shares to be sold by the Company and the Selling Stockholders is herein called the “Firm Shares”, and the aggregate of [___] additional shares of Stock to be sold by the Company is herein called the “Optional Shares”. The Firm Shares and the Optional Shares that the Underwriters elect to purchase pursuant to Section 2

Contract
Root, Inc. • October 5th, 2020 • 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.

ROOT, Inc. INDEMNIFICATION AGREEMENT
Indemnification Agreement • October 20th, 2020 • Root, Inc. • Fire, marine & casualty insurance • Delaware

This Indemnification Agreement (this “Agreement”) is dated as of _________________, 20__ and is between Root, Inc., a Delaware corporation (the “Company”), and ______________ (“Indemnitee”).

FIFTH AMENDED AND RESTATED INVESTORS’ RIGHTS AGREEMENT
Investors’ Rights Agreement • October 5th, 2020 • Root, 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.

November 1, 2020 Alexander Timm Re: Employment Terms Dear Alex:
Root, Inc. • March 4th, 2021 • Fire, marine & casualty insurance

You are currently employed with Root, Inc. (the “Company”). This letter agreement confirms the terms and conditions of your employment (the “Agreement”). As of your execution of this Agreement, you acknowledge and agree that you are no longer eligible for nor entitled to any further compensation or benefits under the terms of any other prior offer letter, other agreement or terms of employment with the Company, all of which are hereby superseded and replaced by this Agreement.

Contract
Purchase Stock • October 20th, 2020 • Root, 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.

EXECUTIVE EMPLOYMENT AGREEMENT
Executive Employment Agreement • March 1st, 2023 • Root, Inc. • Fire, marine & casualty insurance • Ohio

THIS EXECUTIVE EMPLOYMENT AGREEMENT (this “Agreement”) is made as of August 19, 2022 (the “Effective Date”), between Caret Holdings, Inc, a Delaware corporation (and collectively with its parents, subsidiaries, and other corporate affiliates, and its or their successors or assigns (the “Company”), and Megan Binkley (“Executive”). The Company and Executive are each referred to as a “Party” and collectively as the “Parties”.

TERM LOAN AGREEMENT
Term Loan Agreement • May 4th, 2022 • Root, Inc. • Fire, marine & casualty insurance • New York

THIS TERM LOAN AGREEMENT (as amended, restated, amended and restated, supplemented or otherwise modified from time to time, this “Agreement”) is made and entered into as of January 26, 2022, by and among CARET HOLDINGS, INC., a Delaware corporation (the “Borrower”), ROOT, INC., a Delaware corporation (“Holdings”), the other Loan Parties from time to time party hereto, the several banks and other financial institutions and lenders from time to time party hereto (the “Lenders”), and ACQUIOM AGENCY SERVICES LLC (“Acquiom”), as the Administrative Agent for the Lenders.

SHORT-TERM COMMON STOCK PURCHASE WARRANT ROOT, INC.
Root, Inc. • October 1st, 2021 • Fire, marine & casualty insurance • Delaware

THIS SHORT-TERM COMMON STOCK PURCHASE WARRANT (the “Warrant”) certifies that, for value received, Carvana Group, LLC, a Delaware limited liability company, or its permitted successors or assigns (the “Holder”) is entitled, upon the terms and subject to the conditions hereinafter set forth, in whole or in part, at any time on or after the Reference Date (the “Initial Exercise Date”) through 5:00 p.m. (New York City time) on the third (3rd) anniversary of the Reference Date unless earlier terminated as provided herein (the “Termination Date”) but not thereafter, to subscribe for and purchase from Root, Inc., a Delaware corporation (the “Company”), subject to the satisfaction of the Conditions to Exercise, 42,585,140 shares (as subject to adjustment hereunder, the “Warrant Shares”) of Class A Common Stock, which represents the number of shares of Common Stock that would constitute 12.5% of all issued and outstanding shares of Common Stock on a Fully Diluted basis as of August 11, 2021, as

ROOT, INC. RESTRICTED STOCK UNIT AGREEMENT
Restricted Stock Unit Agreement • October 5th, 2020 • Root, Inc. • Fire, marine & casualty insurance • Ohio
LOAN AND SECURITY AGREEMENT
Loan and Security Agreement • October 5th, 2020 • Root, 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 • October 5th, 2020 • Root, 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 • October 5th, 2020 • Root, 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 • October 5th, 2020 • Root, Inc. • Fire, marine & casualty insurance • Ohio
ROOT, INC. COMMON STOCK PURCHASE AGREEMENT October 19, 2020
Common Stock Purchase Agreement • October 20th, 2020 • Root, Inc. • Fire, marine & casualty insurance • California
Separation and Transition Agreement
Separation and Transition Agreement • February 22nd, 2023 • Root, Inc. • Fire, marine & casualty insurance • Ohio

This Separation and Transition Agreement (the “Transition Agreement”) is made and entered into by and between Root, Inc. (“Root” or the “Company”) and Daniel Rosenthal, an individual (“Executive”).

ADVISOR AGREEMENT
Advisor Agreement • July 2nd, 2021 • Root, Inc. • Fire, marine & casualty insurance

This Advisor Agreement (the “Agreement”) is entered into between Root, Inc. (“Company”) and the advisor named on the signature page hereto (“Advisor”) as of July 3, 2021 (“Effective Date”). Company and Advisor agree as follows:

THIRD AMENDMENT TO NOTE PURCHASE AGREEMENT
Note Purchase Agreement • November 10th, 2021 • Root, Inc. • Fire, marine & casualty insurance • New York

11, 2021 (this “Amendment”), by and among CARET HOLDINGS, INC. (f/k/a Root, Inc.), a Delaware corporation (the “Issuer”), ROOT, INC. (f/k/a Root Stockholdings, Inc.), a Delaware corporation (“Holdings”), each of the Noteholders party hereto as “Noteholders”, and WILMINGTON TRUST, NATIONAL ASSOCIATION, in its capacity as Administrative Agent (in such capacity, the “Administrative Agent”).

Root, Inc. Class A Common Stock, par value $0.0001 per share Underwriting Agreement
Underwriting Agreement • October 20th, 2020 • Root, Inc. • Fire, marine & casualty insurance • New York
COMMERCIAL AGREEMENT
Commercial Agreement • October 1st, 2021 • Root, Inc. • Fire, marine & casualty insurance • Delaware

THIS COMMERCIAL AGREEMENT (this “Agreement”) is executed to be effective as of October 1, 2021 (the “Effective Date”), by and between Caret Holdings, Inc., on behalf of itself, subsidiaries, and affiliates (the “Company”), Carvana, LLC, an Arizona limited liability Company (“Dealer”), Carvana Insurance Services, LLC, an Arizona limited liability company (“CIS”), and Carvana Group, LLC, a Delaware limited liability company (“Parent” and, collectively with Dealer and CIS, “Carvana”). The Company and Carvana may be collectively referred to as the “Parties,” and individually as a “Party.”

RE: Retention Bonus Agreement Dear Megan,
Retention Bonus Agreement • May 3rd, 2023 • Root, Inc. • Fire, marine & casualty insurance

We are pleased to offer you this Retention Bonus Agreement (“Agreement”) to encourage your continued employment with Root Inc. or one of its subsidiaries (collectively, “the Company”). This Agreement does not modify the terms of your employment, or any agreement relating to confidentiality, trade secrets, and non-competition/non-solicitation, including any letter agreement, employment agreement or proprietary information and inventions agreement, which shall continue in full force and effect.

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FIRST AMENDMENT TO THE PARTIES’ COMMERCIAL AGREEMENT
Commercial Agreement • August 8th, 2022 • Root, Inc. • Fire, marine & casualty insurance

This First Amendment to the Commercial Agreement (“Amendment”) is entered into and effective this 13th day of May, 2022 (the “Effective Date”), by and between Caret Holdings, Inc. (“Company”), Carvana, LLC (“Dealer”), Carvana Insurance Services, LLC (“CIS”), and Carvana Group, LLC (“Parent”) (collectively, the entities Parent, CIS, and Dealer shall be referred to as “Carvana”). Carvana and Company shall be referred to as the Parties, and each a Party.

INCENTIVE BONUS AGREEMENT
Incentive Bonus Agreement • May 4th, 2022 • Root, Inc. • Fire, marine & casualty insurance • Ohio

This Cash Incentive Agreement (the “Agreement”), dated as of April 1, 2022, is made and entered into by and between Root Inc. (the “Company”) and (the “Employee”) (collectively, the “Parties”).

ROOT, INC. EXECUTIVE COMPENSATION LETTER AGREEMENT
Compensation Letter Agreement • February 23rd, 2022 • Root, Inc. • Fire, marine & casualty insurance

The Compensation Committee recently approved a cash payment to you in the amount of $4,981,250.00 in light of your promotion to Chief Revenue and Operating Officer, effective September 17, 2021, while simultaneously continuing as the Chief Financial Officer, and your successful closing of the Carvana transaction in October 2021 and the BlackRock term loan transaction in January 2022. You will be required to repay the cash payment should you resign without Good Reason (as defined in your Letter Agreement, hereinafter defined) or be terminated for Cause (as defined below) on or prior to December 31, 2022. Accordingly, this letter agreement (this “Agreement”) confirms the terms and conditions of the cash payment to be made by Root, Inc., or one of its wholly owned subsidiaries (collectively, the “Company”), which shall be effective as of the date you execute and return a copy of this Agreement (such date, the “Effective Date”). If you do not execute and return a copy of this Agreement pri

FIRST AMENDMENT TO LETTER AGREEMENT
Letter Agreement • February 23rd, 2022 • Root, Inc. • Fire, marine & casualty insurance

THIS FIRST AMENDMENT TO LETTER AGREEMENT is dated as of February 22, 2022 (this Amendment), by and between Root, Inc. (the “Company”) and Alexander Timm.

FIRST AMENDMENT TO LETTER AGREEMENT
Letter Agreement • February 23rd, 2022 • Root, Inc. • Fire, marine & casualty insurance

THIS FIRST AMENDMENT TO LETTER AGREEMENT is dated as of February 23, 2022 (this Amendment), by and between Root, Inc. (the “Company”) and Daniel Rosenthal.

FIRST AMENDMENT TO THE INVESTMENT AGREEMENT
The Investment Agreement • October 1st, 2021 • Root, Inc. • Fire, marine & casualty insurance

This FIRST AMENDMENT TO THE INVESTMENT AGREEMENT (this “Amendment”), dated as of September 29, 2021, is entered into by and between Root, Inc., a Delaware corporation (the “Company”), and Carvana Group, LLC, a Delaware limited liability company (the “Purchaser”). The Company and the Purchaser are collectively referred to herein as the “Parties” and each, a “Party”.

INVESTMENT AGREEMENT between ROOT, INC. as the Company, and CARVANA GROUP, LLC as the Purchaser, Dated as of August 11, 2021
Investment Agreement • August 12th, 2021 • Root, Inc. • Fire, marine & casualty insurance • Delaware

This Investment Agreement (this “Agreement”), dated as of August 11, 2021, is by and between Root, Inc., a Delaware corporation (the “Company”), and Carvana Group, LLC, a Delaware limited liability company (the “Purchaser”).

AMENDMENT TO THE
Investors’ Rights Agreement • February 23rd, 2022 • Root, Inc. • Fire, marine & casualty insurance • Delaware

This Amendment to the Fifth Amended and Restated Investors’ Rights Agreement, as amended (this “Amendment”), is made as of October 28, 2020 by and between Root, Inc., a Delaware corporation (the “Company”) and the Investors set forth on the signature pages hereto. Capitalized terms not herein defined shall have the meanings ascribed to them in the Fifth Amended and Restated Investors’ Rights Agreement by and among the Company, the Investors and any holder of a Lender Warrant dated as of November 25, 2019 (the “Existing Rights Agreement”).

ROOT, INC. EXECUTIVE RETENTION AGREEMENT
Executive Retention Agreement • August 11th, 2023 • Root, Inc. • Fire, marine & casualty insurance

The Compensation Committee recently approved a cash payment to you in the amount of $750,000.00. You will be required to repay all or a portion of the cash payment should you resign without Good Reason (as defined below) or be terminated for Cause (as defined below) on or prior to August 9, 2025. Accordingly, this agreement (this “Agreement”) confirms the terms and conditions of the cash payment to be made by Root, Inc., or one of its wholly owned subsidiaries (collectively, the “Company”), which shall be effective as of the date you execute and return a copy of this Agreement (such date, the “Effective Date”). If you do not execute and return a copy of this Agreement prior to August 31, 2023, this Agreement shall be null and void.

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