EngageSmart, Inc. (“EngageSmart”) (NYSE: ESMT), a leading provider of vertically tailored customer engagement software and integrated payments solutions, announced today the closing of its previously announced underwritten public offering of 8,000,000 shares of its common stock at a public offering price of $19.00 per share, before deducting underwriting discounts and commissions, all of which were sold by certain of EngageSmart’s stockholders, including affiliates of General Atlantic, L.P. and Summit Partners and certain members of the Company’s management (collectively, the “Selling Stockholders”). The Selling Stockholders received all of the proceeds from the offering. EngageSmart did not sell any of its shares in the offering and did not receive any of the proceeds from the sale of shares in the offering.

Goldman Sachs & Co. LLC, J.P. Morgan, BofA Securities and Citigroup acted as joint book-running managers for the offering. Deutsche Bank Securities, Raymond James, Truist Securities, and William Blair acted as book-runners for the proposed offering. KeyBanc Capital Markets, Needham & Company, Penserra Securities LLC, R. Seelaus & Co., LLC and Roberts & Ryan acted as co-managers for the offering.

The public offering was made pursuant to an automatic shelf registration statement on Form S-3 that was filed by EngageSmart with the U.S. Securities and Exchange Commission (the “SEC”) and automatically became effective upon filing. A final prospectus supplement and accompanying prospectus relating to and describing the terms of the offering have been filed with the SEC and are available on the SEC’s website at www.sec.gov. When available, copies of the final prospectus supplement and accompanying prospectus may be obtained by contacting: Goldman Sachs & Co. LLC, Attention: Prospectus Department, 200 West Street, New York, New York 10282, by phone at (866) 471‐2526 or by email at prospectus-ny@ny.email.gs.com; J.P. Morgan Securities LLC, c/o Broadridge Financial Solutions, 1155 Long Island Avenue, Edgewood, New York 11717, by phone at (866) 803-9204 or by email at prospectus-eq_fi@jpmchase.com; BofA Securities, Attention: Prospectus Department, NC1-004-03-43, 200 North College Street, 3rd Floor, Charlotte, NC 28255-0001, by telephone at (800) 299-1322 or by e-mail at dg.prospectus_requests@bofa.com; or Citigroup Global Markets Inc., c/o Broadridge Financial Solutions, 1155 Long Island Avenue, Edgewood, NY 11717, toll-free: (800) 831-9146 or by e-mail at prospectus@citi.com.

This release shall not constitute an offer to sell or a solicitation of an offer to buy these securities, nor shall there be any sale of these securities in any state or other jurisdiction in which such offer, solicitation or sale would be unlawful prior to the registration or qualification under the securities laws of any such state or other jurisdiction.

About EngageSmart

EngageSmart is a leading provider of vertically tailored customer engagement software and integrated payments solutions. Our mission is to simplify customer and client engagement to allow our customers to focus resources on initiatives that improve their businesses and better serve their communities. EngageSmart offers single instance, multi-tenant, true Software-as-a-Service vertical solutions, including SimplePractice, InvoiceCloud, HealthPay24 and DonorDrive, that are designed to simplify its customers’ engagement with their clients by driving digital adoption and self-service. As of December 31, 2022, EngageSmart serves approximately 99,300 customers in the SMB Solutions segment and approximately 3,300 customers in the Enterprise Solutions segment across several core verticals: Health & Wellness, Government, Utilities, Financial Services, Healthcare, and Giving.

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