Lemonade, Inc. Sample Contracts

Underwriting Agreement
Underwriting Agreement • January 11th, 2021 • Lemonade, Inc. • Fire, marine & casualty insurance • New York

Lemonade 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 common stock, par value $0.00001 per share (“Stock”) of the Company and the stockholders of the Company named in Schedule II hereto (the “Selling Stockholders”) propose, subject to the terms and conditions stated in this Agreement, to sell to the Underwriters an aggregate of [•] shares. 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 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 hereof are herein collectively called the “Shares.”

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Underwriting Agreement
Underwriting Agreement • June 15th, 2020 • Lemonade, Inc. • Fire, marine & casualty insurance • New York

Lemonade, 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 (the “Firm Shares”) and, at the election of the Underwriters, up to [•] additional shares (the “Optional Shares”) of common stock, par value $0.00001 per share (“Stock”) of the Company (the Firm Shares and the Optional Shares that the Underwriters elect to purchase pursuant to Section 2 hereof being collectively called the “Shares”).

METROMILE, INC. INDEMNIFICATION AGREEMENT
Indemnification Agreement • December 14th, 2021 • Lemonade, Inc. • Fire, marine & casualty insurance • Delaware

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

INDEMNIFICATION AND ADVANCEMENT AGREEMENT
Indemnification and Advancement Agreement • June 8th, 2020 • Lemonade, Inc. • Fire, marine & casualty insurance • Delaware

This Indemnification and Advancement Agreement (“Agreement”) is made as of , 2020 by and between Lemonade, Inc., a Delaware corporation (the “Company”), and , a member of the Board of Directors or an officer of the Company (“Indemnitee”). This Agreement supersedes and replaces any and all previous Agreements between the Company and Indemnitee covering indemnification and advancement.

AGREEMENT AND PLAN OF MERGER by and among LEMONADE, INC., a Delaware corporation; CITRUS MERGER SUB A, INC., a Delaware corporation; CITRUS MERGER SUB B, LLC, a Delaware limited liability company; and METROMILE, INC., a Delaware corporation Dated as...
Agreement and Plan of Merger • November 9th, 2021 • Lemonade, Inc. • Fire, marine & casualty insurance • Delaware

THIS AGREEMENT AND PLAN OF MERGER (this “Agreement”) is made and entered into as of November 8, 2021, by and among Lemonade, Inc., a Delaware corporation (“Parent”); Citrus Merger Sub A, Inc., a Delaware corporation and a direct, wholly owned Subsidiary of Parent (“Acquisition Sub I”); Citrus Merger Sub B, LLC, a Delaware limited liability company and a direct, wholly owned Subsidiary of Parent (“Acquisition Sub II,” and together with Acquisition Sub I, the “Acquisition Subs”); and Metromile, Inc., a Delaware corporation (the “Company”). Certain capitalized terms used in this Agreement are defined in Exhibit A.

OFFICE LEASE 425 MKT REIT, LLC (LANDLORD) AND METROMILE, INC. (TENANT) 425 MARKET STREET San Francisco, California
Workletter Agreement • December 14th, 2021 • Lemonade, Inc. • Fire, marine & casualty insurance • California
LEMONADE, INC. STOCK PURCHASE AGREEMENT
Stock Purchase Agreement • June 8th, 2020 • Lemonade, Inc. • Fire, marine & casualty insurance • New York

This Stock Purchase Agreement (the “Agreement”) is entered into as of March 8, 2017 by and between Lemonade, Inc., a Delaware corporation (the “Company”), and John Peters (“Purchaser”).

Contract
Interests and Liabilities Agreement • August 4th, 2023 • Lemonade, Inc. • Fire, marine & casualty insurance • New York

[***] Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10) because it is both not material and the type of information that the registrant treats as private or confidential.

LEMONADE, INC. STOCK OPTION GRANT NOTICE AND STOCK OPTION AGREEMENT
Stock Option Agreement • January 11th, 2021 • Lemonade, Inc. • Fire, marine & casualty insurance • Delaware

Lemonade, Inc., a Delaware corporation (the “Company”), pursuant to its 2020 Incentive Award Plan, as amended from time to time (the “Plan”), hereby grants to the holder listed below (“Participant”) an option to purchase the number of Shares set forth below (the “Option”). The Option is subject to the terms and conditions set forth in this Stock Option Grant Notice (the “Grant Notice”), the Plan and the Stock Option Agreement attached hereto as Exhibit A including any Appendix thereto (the “Agreement”), each of which is incorporated into this Grant Notice by reference. Unless otherwise defined herein, the terms defined in the Plan shall have the same defined meanings in this Grant Notice and the Agreement.

AMENDED AND RESTATED REGISTRATION RIGHTS AGREEMENT
Registration Rights Agreement • December 14th, 2021 • Lemonade, Inc. • Fire, marine & casualty insurance • New York

THIS AMENDED AND RESTATED REGISTRATION RIGHTS AGREEMENT (this “Agreement”), dated as of February 9, 2021, is made and entered into by and among each of INSU Acquisition Corp. II, a Delaware corporation (the “Company”), Insurance Acquisition Sponsor II, LLC, a Delaware limited liability company, Dioptra Advisors II, LLC, a Delaware limited liability company and INSU II PIPE Sponsor, LLC (collectively, the “Sponsor”), Cantor Fitzgerald & Co., a New York general partnership (“Cantor”), the Former MetroMile Stockholders (as defined below) and any person or entity who hereafter becomes a party to this Agreement pursuant to Section 5.2 of this Agreement (each, a “Holder” and collectively, the “Holders”).

Severance Agreement
Severance Agreement • August 12th, 2020 • Lemonade, Inc. • Fire, marine & casualty insurance • New York

THIS SEVERANCE AGREEMENT (the “Severance Agreement”) is entered into as of the Effective Date (as defined below) between Lemonade, Inc. (together with any Affiliate that may employ you from time to time, the “Company”) and Tim Bixby (“Executive” or “you”).

METROMILE, INC. OMNIBUS AMENDMENT NO. 2 TO THE NOTE PURCHASE AND SECURITY AGREEMENT February 9, 2021
Note Purchase and Security Agreement • December 14th, 2021 • Lemonade, Inc. • Fire, marine & casualty insurance • New York

This OMNIBUS AMENDMENT NO. 2 (this “Amendment”) to the Note Purchase and Security Agreement, dated as of April 14, 2020, by and among Metromile, Inc. (the “Company”), INSU Acquisition Corp. II, a Delaware corporation (the “Parent”), the other undersigned Guarantors, the Holders, and the Agent (as each term is defined therein, as amended prior to the date hereof, the “Note Purchase Agreement”) is entered into as of the date hereof, by and among the Company, HSCM BERMUDA FUND LTD. (“Bermuda”) and HS SANTANONI LP (“Santanoni”). This Amendment amends the Note Purchase Agreement and each Note issued pursuant thereto. All capitalized terms not defined herein shall have the meanings ascribed to them in the Note Purchase Agreement.

METROMILE, INC.
Lemonade, Inc. • December 14th, 2021 • Fire, marine & casualty insurance

On behalf of Metromile, Inc. (the “Company”), I am pleased to offer you continued employment at the Company on the terms set forth in this offer letter agreement (the “Agreement”). This Agreement shall become effective on the date that it is signed by you (the “Effective Date”) and shall amend and restate any prior offer letter or employment agreement between you and the Company, including your offer letter dated January 30, 2013.

AWS Customer Agreement
Aws Customer Agreement • June 8th, 2020 • Lemonade, Inc. • Fire, marine & casualty insurance

This AWS Customer Agreement (this “Agreement”) contains the terms and conditions that govern your access to and use of the Service Offerings (as defined below) and is an agreement between the applicable AWS Contracting Party specified in Section 14 below (also referred to as “AWS,” “we,” “us,” or “our”) and you or the entity you represent (“you” or “your”). This Agreement takes effect when you click an “I Accept” button or check box presented with these terms or, if earlier, when you use any of the Service Offerings (the “Effective Date”). You represent to us that you are lawfully able to enter into contracts (e.g., you are not a minor). If you are entering into this Agreement for an entity, such as the company you work for, you represent to us that you have legal authority to bind that entity. Please see Section 14 for definitions of certain capitalized terms used in this Agreement.

VOTING AND SUPPORT AGREEMENT
Voting and Support Agreement • November 9th, 2021 • Lemonade, Inc. • Fire, marine & casualty insurance • Delaware

THIS VOTING AND SUPPORT AGREEMENT (this “Agreement”) is made and entered into as of November 8, 2021, by and among Lemonade, Inc., a Delaware corporation (“Parent”); and [ ], a [ ] (“Stockholder”).

AMENDED AND RESTATED PERSONAL EMPLOYMENT AGREEMENT
Personal Employment Agreement • June 23rd, 2020 • Lemonade, Inc. • Fire, marine & casualty insurance

This Amended and Restated Personal Employment Agreement (“Agreement”) is entered into as of the Effective Date (as defined below), by and between Lemonade Ltd., a private company incorporated under the laws of the State of Israel having its principal office at 26 Eliezer Kaplan St., Tel Aviv, 6473427 Israel (the “Company”) and the employee whose details are specified in Annex A hereto (the “Employee” and, together with the Company, the “Parties”).

AMENDED AND RESTATED PERSONAL EMPLOYMENT AGREEMENT
Personal Employment Agreement • August 12th, 2020 • Lemonade, Inc. • Fire, marine & casualty insurance

This Amended and Restated Personal Employment Agreement (“Agreement”) is entered into as of the Effective Date (as defined below), by and between Lemonade Ltd., a private company incorporated under the laws of the State of Israel having its principal office at 38 Keren Hayesod Street, Jerusalem, Israel ((together with Lemonade, Inc. and any affiliate or subsidiary thereof that may employ the Employee from time to time, the “Company”) and the employee whose details are specified in Annex A hereto (the “Employee” and, together with the Company, the “Parties”).

AMENDED AND RESTATED INVESTORS’ RIGHTS AGREEMENT
Investors’ Rights Agreement • June 8th, 2020 • Lemonade, Inc. • Fire, marine & casualty insurance • New York

This AMENDED AND RESTATED INVESTORS’ RIGHTS AGREEMENT (the “Agreement”) is made as of June 26, 2019, by and among Lemonade, Inc., a Delaware corporation (the “Company”), and the investors listed on Schedule A hereto, each of which is herein referred to as an “Investor” and collectively as the “Investors”, each of the stockholders listed on Schedule B hereto, each of whom is herein referred to as a “Key Holder” and collectively as the “Key Holders”).

LEMONADE, INC. US OPTION AGREEMENT Made as of the [_______] day of [______]
Option Agreement • January 11th, 2021 • Lemonade, Inc. • Fire, marine & casualty insurance

WHEREAS the Company duly adopted and the Board approved the A&R 2015 Incentive Share Option Plan, as might be further amended from time to time, a copy of which is attached as Exhibit A attached hereto, forming an integral part hereof (the “Option Plan” or the “ISOP”); and

AMENDED AND RESTATED VOTING AGREEMENT
Adoption Agreement • June 8th, 2020 • Lemonade, Inc. • Fire, marine & casualty insurance • New York

This AMENDED AND RESTATED VOTING AGREEMENT (the “Agreement”) is made and entered into as of June 26, 2019, by and among Lemonade, Inc., a Delaware corporation (the “Company”), the holders of the Company’s Series Seed Preferred Stock, par value $0.00001 per share (the “Series Seed Stock”), the holders of the Company’s Series A Preferred Stock, par value $0.00001 per share (the “Series A Stock”), the holders of the Company’s Series B Preferred Stock, par value $0.00001 per share (the “Series B Stock”), the holders of the Company’s Series C Preferred Stock, par value $0.00001 per share (the “Series C Stock”), the holders of the Company’s Series D Preferred Stock, par value $0.00001 per share (together, the “Series D Stock” and collectively with the Series Seed Stock, the Series A Preferred Stock, the Series B Stock and the Series C Stock, the “Preferred Stock”) listed on the Schedule of Investors attached as Schedule A hereto (together with any subsequent investors, or transferees, who be

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PERSONAL EMPLOYMENT AGREEMENT
Personal Employment Agreement • June 8th, 2020 • Lemonade, Inc. • Fire, marine & casualty insurance

This Personal Employment Agreement (“Agreement”) is entered into this day of July 2015 (the “Effective Date”), by and between Lemonade Ltd., a private company incorporated under the laws of the State of Israel having its principal office at 38 Keren Hayesod Street, Jerusalem, Israel (the “Company”) and the employee whose details are specified in Annex A hereto (the “Employee”).

Severance Agreement
Severance Agreement • November 9th, 2021 • Lemonade, Inc. • Fire, marine & casualty insurance

THIS SEVERANCE AGREEMENT (the “Severance Agreement”) is entered into as of the Effective Date (as defined below) between Lemonade, Inc. (together with any Affiliate that may employ you from time to time, the “Company”) and Adina Eckstein (“Executive” or “you”).

METROMlLE, INC. AT-WILL EMPLOYMENT, CONFIDENTIAL INFORMATION, INVENTION ASSIGNMENT, AND ARBITRATION AGREEMENT
And Arbitration Agreement • December 14th, 2021 • Lemonade, Inc. • Fire, marine & casualty insurance • California

As a condition of my employment with MetroMile, Inc., its subsidiaries, affiliates, successors or assigns (together, the “Company”), and in consideration of my employment with the Company and my receipt of the compensation now and hereafter paid to me by Company, I agree to the following provisions of this MetroMile, Inc. At-Will Employment, Confidential Information, Invention Assignment, and Arbitration Agreement (this “Agreement”):

LEMONADE, INC. 2020 INCENTIVE AWARD PLAN STOCK OPTION GRANT NOTICE AND STOCK OPTION AGREEMENT
Stock Option Grant Notice And • May 12th, 2021 • Lemonade, Inc. • Fire, marine & casualty insurance • Delaware

Lemonade, Inc., a Delaware corporation (the “Company”), pursuant to its 2020 Incentive Award Plan, as amended from time to time (the “Plan”) and the Israeli Appendix for Israeli Taxpayers, as amended from time to time (the “IL Appendix”), hereby grants to the IL Optionee listed below (the “Participant”) an option to purchase the number of Shares set forth below (the “Option”). The Option is subject to the terms and conditions set forth in this Stock Option Grant Notice (the “Grant Notice”), the Plan and the Stock Option Agreement attached hereto as Exhibit A (the “Agreement”), each of which is incorporated into this Grant Notice by reference. Unless otherwise defined herein, the terms defined in the Plan shall have the same defined meanings in this Grant Notice and the Agreement.

LEMONADE, INC. 2020 INCENTIVE AWARD PLAN RESTRICTED STOCK UNIT AWARD GRANT NOTICE AND RESTRICTED STOCK UNIT AGREEMENT
Restricted Stock Unit Agreement • August 11th, 2021 • Lemonade, Inc. • Fire, marine & casualty insurance • Delaware

Lemonade, Inc., a Delaware corporation (the “Company”), pursuant to its 2020 Incentive Award Plan, as amended from time to time (the “Plan”), hereby grants to the holder listed below (“Participant”) the number of Restricted Stock Units set forth below (the “RSUs”). The RSUs are subject to the terms and conditions set forth in this Restricted Stock Unit Grant Notice (the “Grant Notice”), the Restricted Stock Unit Agreement attached hereto as Exhibit A including any Appendix thereto (the “Agreement”), the Plan, and the Appendix for Israeli Taxpayers, as adopted by the Company and amended from time to time (the “IL Appendix”), each of which is incorporated herein by reference. Unless otherwise defined herein, the terms defined in the Plan shall have the same defined meanings in the Grant Notice and the Agreement. All references to the Plan under this Grant Notice, shall refer to the IL Appendix as well, and the term “Plan” shall include the IL Appendix.

LEMONADE, INC. AMENDED AND RESTATED EMPLOYMENT AGREEMENT
Employment Agreement • June 23rd, 2020 • Lemonade, Inc. • Fire, marine & casualty insurance • New York

THIS AMENDED AND RESTATED EMPLOYMENT AGREEMENT (“Agreement”) is made as of the Effective Date (as defined below), between Lemonade, Inc., a Delaware corporation (the “Company”) and John Peters.(the “Employee”) (collectively referred to herein as the “Parties”).

METROMILE, INC. CONFIDENTIAL INFORMATION AND INVENTION ASSIGNMENT AGREEMENT
Invention Assignment Agreement • December 14th, 2021 • Lemonade, Inc. • Fire, marine & casualty insurance • California

As a condition of my business relationship with MetroMile, Inc., its subsidiaries, affiliates, successors or assigns (together, the “Company”), and in consideration of my business relationship with the Company and my receipt of the compensation now and hereafter paid to me on behalf of Company, I agree to the following provisions of this MetroMile, Inc. Confidential Information and Invention Assignment Agreement (this “Agreement”):

LEMONADE, INC. AMENDED AND RESTATED EMPLOYMENT AGREEMENT
Severance Agreement • August 12th, 2020 • Lemonade, Inc. • Fire, marine & casualty insurance • New York

THIS AMENDED AND RESTATED EMPLOYMENT AGREEMENT (“Agreement”) is made as of the Effective Date (as defined below), between Lemonade, Inc., a Delaware corporation (the “Company”) and John Peters.(the “Employee”) (collectively referred to herein as the “Parties”).

METROMILE, INC. AT-WILL EMPLOYMENT, CONFIDENTIAL INFORMATION, INVENTION ASSIGNMENT, AND ARBITRATION AGREEMENT
Lemonade, Inc. • December 14th, 2021 • Fire, marine & casualty insurance • California

As a condition of my employment with MetroMile, Inc., its subsidiaries, affiliates, successors or assigns (together, the “Company”), and in consideration of my employment with the Company and my receipt of the compensation now and hereafter paid to me by Company, I agree to the following provisions of this MetroMile, Inc. At-Will Employment, Confidential Information, Invention Assignment, and Arbitration Agreement (this “Agreement”):

Certain identified information has been excluded from this exhibit because it is both not material and is the type that the registrant treats as private or confidential. Information that was omitted has been noted in this document with a placeholder...
Omnibus Agreement • October 20th, 2022 • Lemonade, Inc. • Fire, marine & casualty insurance • Delaware

This Omnibus Agreement, dated as of October 14, 2022 (this “Agreement”), is by and between Lemonade, Inc., a Delaware public benefit corporation (the “Company”), and Chewy Insurance Services, LLC, a Delaware limited liability company (“Warrantholder”).

METROMILE, INC.
Restricted Stock Purchase Agreement • December 14th, 2021 • Lemonade, Inc. • Fire, marine & casualty insurance • California

Unless otherwise defined herein, the terms defined in the 2011 Equity Incentive Plan (the “Plan”) shall have the same defined meanings in this Stock Option Agreement – Early Exercise (the “Option Agreement”).

LEMONADE, INC. EMPLOYMENT AGREEMENT
Employment Agreement • June 8th, 2020 • Lemonade, Inc. • Fire, marine & casualty insurance • New York

THIS EMPLOYMENT AGREEMENT (“Agreement”) is made as of the 3rd day of October 2016, effective as of September 26, 2016, between Lemonade, Inc., a Delaware corporation (the “Company”) and John Peters, residing at [ ] (the “Employee”).

Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10). Such excluded information is both not material and is the type that the registrant treats as private or confidential. ADDENDUM NO. 2 to the WHOLE...
Share Reinsurance Contract • August 11th, 2021 • Lemonade, Inc. • Fire, marine & casualty insurance

Effective 12:01 a.m., Standard Time, July 1, 2021, the Subscribing Reinsurer’s participation shall be extended for an additional 12 months, and shall expire at 12:01 a.m., Standard Time, July 1, 2022. In consideration thereof, the Contract is amended as follows:

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