EngageSmart, Inc. Sample Contracts

EngageSmart, Inc. Shares of Common Stock, par value $0.001 per share Underwriting Agreement
EngageSmart, Inc. • March 1st, 2023 • Services-prepackaged software • New York

Certain stockholders named in Schedule 2 hereto (the “Selling Stockholders”) of EngageSmart, Inc., a Delaware corporation (the “Company”), propose to sell to the several underwriters listed in Schedule 1 hereto (collectively, the “Underwriters”), for whom you are acting as representatives (the “Representatives”), an aggregate of 8,000,000 shares (the “Underwritten Shares”) of common stock, par value $0.001 per share (the “Common Stock”), of the Company and, at the option of the Underwriters, up to an additional 1,200,000 shares of Common Stock (the “Option Shares”). The Underwritten Shares and the Option Shares are herein referred to as the “Shares.” The shares of Common Stock of the Company to be outstanding after giving effect to the sale of the Shares are referred to herein as the “Stock.” To the extent that there is not more than one Selling Stockholder named in Schedule 2, the term Selling Stockholders shall mean either the singular or plural as the context requires.

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INDEMNIFICATION AND ADVANCEMENT AGREEMENT
Indemnification and Advancement Agreement • September 16th, 2021 • EngageSmart, LLC • Services-prepackaged software • Delaware

This Indemnification and Advancement Agreement (“Agreement”) is made as of __________, 2021 by and between EngageSmart, 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.

EMPLOYMENT AGREEMENT
Employment Agreement • May 5th, 2022 • EngageSmart, Inc. • Services-prepackaged software • Delaware

THIS EMPLOYMENT AGREEMENT (this “Agreement”) is entered into by and between EngageSmart, Inc. (the “Company”) and Scott Semel (the “Executive”) as of March 1, 2022 (the “Effective Date”).

ENGAGESMART, INC. REGISTRATION RIGHTS AGREEMENT
Registration Rights Agreement • November 10th, 2021 • EngageSmart, Inc. • Services-prepackaged software • Delaware

This REGISTRATION RIGHTS AGREEMENT (this “Agreement”) is made as of September 22, 2021, by and among EngageSmart, Inc., a Delaware corporation (the “Company”), General Atlantic (IC), L.P., a Delaware limited partnership (together with its affiliated investment entities, “General Atlantic”), Summit Partners Growth Equity Fund VIII-A, L.P., a Delaware limited partnership, Summit Partners Growth Equity Fund VIII-B, L.P., a Delaware limited partnership, Summit Partners Entrepreneur Advisors Fund I, L.P., a Delaware limited partnership, Summit Investors I, LLC, a Delaware limited liability company and Summit Investors I (UK), L.P., a Cayman Islands exempted limited partnership (collectively, “Summit”), and each of the investors listed on the signature pages hereto under the caption “Investors” (collectively, the “Investors” and individually, an “Investor”), and each other Person listed on the signature pages hereto under the caption “Other Holders” or who executes a Joinder as an “Other Hol

EMPLOYMENT AGREEMENT
Employment Agreement • September 13th, 2021 • EngageSmart, LLC • Services-prepackaged software • Delaware

THIS EMPLOYMENT AGREEMENT (this “Agreement”) is entered into by and between EngageSmart, LLC (the “Company”) and Robert Bennett (the “Executive”).

EMPLOYMENT AGREEMENT
Employment Agreement • September 13th, 2021 • EngageSmart, LLC • Services-prepackaged software • Delaware

THIS EMPLOYMENT AGREEMENT (this “Agreement”) is entered into by and between EngageSmart, LLC (the “Company”) and Cassandra Hudson (the “Executive”).

AGREEMENT AND PLAN OF MERGER by and among ICEFALL PARENT, LLC, ICEFALL MERGER SUB, INC. and ENGAGESMART, INC. Dated as of October 23, 2023
Agreement and Plan of Merger • October 23rd, 2023 • EngageSmart, Inc. • Services-prepackaged software • Delaware

THIS AGREEMENT AND PLAN OF MERGER (this “Agreement”) is made and entered into as of October 23, 2023, by and among ICEFALL PARENT, LLC, a Delaware limited liability company (“Parent”), ICEFALL MERGER SUB, INC., a Delaware corporation and wholly owned subsidiary of Parent (“Merger Sub”, and together with Parent, the “Buyer Parties”), and ENGAGESMART, INC., a Delaware corporation (the “Company”). Each of the Company, Parent and Merger Sub is sometimes referred to as a “Party.” All capitalized terms that are used in this Agreement have the respective meanings given to them in Article I.

SIMPLE PRACTICE LLC SECOND AMENDED & RESTATED EMPLOYMENT AGREEMENT
Employment Agreement • March 3rd, 2022 • EngageSmart, Inc. • Services-prepackaged software • California

SECOND AMENDED & RESTATED EMPLOYMENT AGREEMENT (this “Agreement”) dated as of November 30, 2021 (the “Effective Date”), between SIMPLEPRACTICE, LLC, a California limited liability company, and EngageSmart, Inc., a Delaware corporation and parent of SimplePractice, LLC (collectively the “Company”), and Howard Spector (“the Employee”).

SUPPORT AGREEMENT
Support Agreement • October 23rd, 2023 • EngageSmart, Inc. • Services-prepackaged software • Delaware

This Support Agreement (this “Agreement”), dated as of October 23, 2023, is entered into by and among EngageSmart, Inc., a Delaware corporation (the “Company”), General Atlantic (IC), L.P., a Delaware limited partnership and General Atlantic (IC) SPV, L.P., a Delaware limited partnership (collectively, the “Stockholders” and each, a “Stockholder”) and Icefall Parent, LLC, a Delaware limited liability company (“Parent”). Capitalized terms used but not defined herein shall have the meanings given to them in the Merger Agreement (as defined below).

AMENDMENT No. 1
Revolving Credit Agreement • August 3rd, 2023 • EngageSmart, Inc. • Services-prepackaged software • New York

This REVOLVING CREDIT AGREEMENT dated as of September [  ]27, 2021 (as further amended, restated, supplemented, waived, replaced (whether or not upon termination, and whether with the original lenders or otherwise) this “Agreement”) among EngageSmart, Inc., a Delaware corporation (the “Borrower”), each lender from time to time party hereto (collectively, the “Lenders” and each, individually, a “Lender”), the L/C Issuers from time to time party hereto and JPMorgan Chase Bank, N.A. (“JPMCB”), as Administrative Agent and as Collateral Agent.

ENGAGESMART, INC. AMENDMENT TO EMPLOYMENT AGREEMENT
Employment Agreement • November 10th, 2021 • EngageSmart, Inc. • Services-prepackaged software • Delaware

THIS AMENDMENT TO EMPLOYMENT AGREEMENT (this “Amendment”), is made as of October 21, 2021 (the “Effective Date”), by and between EngageSmart, Inc., a Delaware corporation (the “Company”), and Thomas Griffin (“Executive”). Capitalized terms not otherwise defined herein shall have the meanings ascribed thereto in the Employment Agreement (as defined below).

CREDIT AGREEMENT Dated as of February 11, 2019 among HANCOCK MERGER SUB, INC. (which on the Closing Date shall be merged with and into Invoice Cloud, Inc., with Invoice Cloud, Inc. surviving the Merger), as Initial Borrower HANCOCK MIDCO, LLC, as...
Credit Agreement • September 13th, 2021 • EngageSmart, LLC • Services-prepackaged software • New York

NOW, THEREFORE, in consideration of the premises and the agreements, provisions and covenants herein contained, the parties hereto agree as follows:

STOCKHOLDERS AGREEMENT
Stockholders Agreement • November 10th, 2021 • EngageSmart, Inc. • Services-prepackaged software • Delaware

This STOCKHOLDERS AGREEMENT (this “Agreement”) is made and entered into as of September 22, 2021, by and among EngageSmart, Inc. (formerly EngageSmart, LLC), a Delaware corporation (the “Company”), General Atlantic (IC), L.P., a Delaware limited partnership (together with its affiliated investment entities, the “GA Stockholder”), Summit Partners Growth Equity Fund VIII-A, L.P., a Delaware limited partnership, Summit Partners Growth Equity Fund VIII-B, L.P., a Delaware limited partnership, Summit Partners Entrepreneur Advisors Fund I, L.P., a Delaware limited partnership, Summit Investors I, LLC, a Delaware limited liability company, and Summit Investors I (UK), L.P., a Cayman Islands exempted limited partnership (collectively, the “Summit Stockholder” and, together with the GA Stockholder, the “Lead Stockholders”) and Robert Bennett, an individual (“Bennett” and, together with the Lead Stockholders, the ‘Stockholders’ and individually, a “Stockholder”).

LIMITED GUARANTEE
Limited Guarantee • November 20th, 2023 • EngageSmart, Inc. • Services-prepackaged software

THIS LIMITED GUARANTEE, dated as of October 23, 2023 (this “Limited Guarantee”), is made by Vista Equity Partners Fund VIII, L.P., a Delaware limited partnership (the “Guarantor”), in favor of EngageSmart, Inc., a Delaware corporation (the “Company”). Reference is hereby made to that certain Agreement and Plan of Merger, dated on or about the date hereof (as the same may be amended, modified or restated in accordance with the terms thereof, the “Merger Agreement”), by and among the Company, Icefall Parent, LLC, a Delaware limited liability company (“Parent”) and Icefall Merger Sub, Inc., a Delaware corporation and a wholly owned subsidiary of Parent (“Merger Sub” and together with Parent, the “Buyer Parties”). Capitalized terms used, but not defined, herein shall have the meanings ascribed to them in the Merger Agreement.

ENGAGESMART, INC. AMENDMENT NO. 1 TO REGISTRATION RIGHTS AGREEMENT November 2, 2022
Registration Rights Agreement • November 3rd, 2022 • EngageSmart, Inc. • Services-prepackaged software • Delaware

This Amendment No. 1 to Registration Rights Agreement (this “Amendment”) is made, entered into and effective as of November 2, 2022, and amends that certain Registration Rights Agreement, dated as of September 22, 2021 (the “Registration Rights Agreement”), by and among EngageSmart, Inc., a Delaware corporation (the “Company”), and the Investors and Other Holders named therein (such Investors and Other Holders, each, a “Holder” and collectively, the “Holders”). All capitalized terms used herein and not otherwise defined shall have the respective meanings assigned to such terms in the Registration Rights Agreement.

SECOND AMENDED AND RESTATED LIMITED LIABILITY COMPANY AGREEMENT OF HANCOCK PARENT, LLC, a Delaware Limited Liability Company Dated as of February 11, 2019
Limited Liability Company Agreement • August 27th, 2021 • EngageSmart, LLC • Services-prepackaged software • Delaware

This SECOND AMENDED AND RESTATED LIMITED LIABILITY COMPANY AGREEMENT (this “Agreement”) of HANCOCK PARENT, LLC (the “Company”) is made and entered into as of this 11th day of February, 2019 (the “Effective Date”), by and among each Person listed as a Shareholder (as defined herein) on Schedule A attached hereto as of the date hereof and each Person subsequently admitted as a Shareholder of the Company in accordance with the terms hereof.

SUPPORT AGREEMENT
Support Agreement • October 23rd, 2023 • EngageSmart, Inc. • Services-prepackaged software • Delaware

This Support Agreement (this “Agreement”), dated as of October 22, 2023, is entered into by and among EngageSmart, Inc., a Delaware corporation (the “Company”), the undersigned stockholders (collectively, the “Stockholders” and each, a “Stockholder”) and Icefall Parent, LLC, a Delaware limited liability company (“Parent”). Capitalized terms used but not defined herein shall have the meanings given to them in the Merger Agreement (as defined below).

INVOICE CLOUD INC. EMPLOYMENT AGREEMENT
Employment Agreement • August 27th, 2021 • EngageSmart, LLC • Services-prepackaged software • Delaware

EMPLOYMENT AGREEMENT (this “Agreement”) dated as of April 30, 2015 (the “Effective Date”), between INVOICE CLOUD INC., a Delaware corporation (the “Company”), and Robert Bennett (the “Employee”).

HANCOCK PARENT, LLC INCENTIVE STOCK OPTION AGREEMENT PURSUANT TO THE HANCOCK PARENT, LLC AMENDED AND RESTATED 2015 STOCK OPTION PLAN
Agreement • August 27th, 2021 • EngageSmart, LLC • Services-prepackaged software • Delaware

AGREEMENT (“Agreement”), dated as of November 1, 2019 (the “Grant Date”), between Hancock Parent, LLC, a Delaware limited liability company (the “Company”), and David Mangum (the “Participant”).

CONFIDENTIAL SEPARATION AND RELEASE AGREEMENT
Confidential Separation and Release Agreement • March 3rd, 2022 • EngageSmart, Inc. • Services-prepackaged software • Delaware

This Confidential Separation and Release Agreement (the “Agreement”) is entered into by and between Thomas Griffin (“Employee”) and EngageSmart, Inc. (the “Company”), effective as of the eighth (8th) day following the date on which Employee signs this Agreement if not revoked in accordance with Section 6(d) below (the “Effective Date”). The purpose of this Agreement is to provide separation pay to ease Employee’s transition from the Company and to settle and resolve any and all disputes and controversies of any nature existing between Employee and the Company, including, but not limited to, any claims arising out of Employee’s employment with, and separation from, the Company.

TERMS AND CONDITIONS OF EMPLOYMENT
Terms and Conditions of Employment • August 27th, 2021 • EngageSmart, LLC • Services-prepackaged software • Massachusetts

This Terms and Conditions of Employment (“Terms and Conditions”) is made as of this 14 day of October 2020, between Invoice Cloud, Inc. (the “Company”) and Cassandra Hudson, whose address is ### (“Employee or “You” or “Your”).

ENGAGESMART, LLC INCENTIVE STOCK OPTION AGREEMENT PURSUANT TO THE ENGAGESMART, LLC AMENDED AND RESTATED 2015 STOCK OPTION PLAN
Incentive Stock Option Agreement • August 27th, 2021 • EngageSmart, LLC • Services-prepackaged software • Delaware

AGREEMENT (“Agreement”), dated as of ____, 20__ (the “Grant Date”), between EngageSmart, LLC, a Delaware limited liability company (the “Company”), and ___________ (the “Participant”).

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REVOLVING CREDIT AGREEMENT dated as of September 27, 2021 among ENGAGESMART, INC., as the Borrower, JPMORGAN CHASE BANK, N.A., as Administrative Agent, Collateral Agent and an L/C Issuer, The Other Lenders and L/C Issuers Party Hereto, and JPMORGAN...
Revolving Credit Agreement • October 1st, 2021 • EngageSmart, Inc. • Services-prepackaged software • London

This REVOLVING CREDIT AGREEMENT dated as of September 27, 2021 (as further amended, restated, supplemented, waived, replaced (whether or not upon termination, and whether with the original lenders or otherwise) this “Agreement”) among EngageSmart, Inc., a Delaware corporation (the “Borrower”), each lender from time to time party hereto (collectively, the “Lenders” and each, individually, a “Lender”), the L/C Issuers from time to time party hereto and JPMorgan Chase Bank, N.A. (“JPMCB”), as Administrative Agent and as Collateral Agent.

Vista Equity Partners Fund VIII, L.P. c/o Vista Equity Partners Management, LLC Four Embarcadero Center, 20th Floor San Francisco, CA 94111 October 23, 2023
EngageSmart, Inc. • November 20th, 2023 • Services-prepackaged software

Reference is made to that certain (i) Agreement and Plan of Merger (as the same may be amended, modified or restated in accordance with the terms thereof, the “Merger Agreement”), dated as of the date hereof, by and among Icefall Parent, LLC, a Delaware limited liability company (“Parent” or “you”), Icefall Merger Sub, Inc., a Delaware corporation (“Merger Sub” and together with Parent, the “Buyer Parties”), and EngageSmart, Inc., a Delaware corporation (the “Company”) and (ii) Support Agreement, dated as of the date hereof, by and among the Company, the Stockholder (as defined therein) and Parent (the “Support Agreement”). Capitalized terms used, but not otherwise defined, in this letter shall have the meanings ascribed to such terms in the Merger Agreement.

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