0001193125-23-280779 Sample Contracts

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.

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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
Support Agreement • November 20th, 2023 • EngageSmart, Inc. • 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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