EngageSmart, Inc. (“EngageSmart”) (NYSE: ESMT), a leading provider of vertically tailored customer engagement software and integrated payments solutions, announced today the commencement of a proposed underwritten public offering of 8,000,000 shares of its common stock being offered for sale by certain of its stockholders, including affiliates of General Atlantic, L.P. and Summit Partners and certain members of the Company’s management (collectively, the “Selling Stockholders”). In addition, certain of the Selling Stockholders have granted the underwriters a 30-day option to purchase up to 1,200,000 additional shares of common stock at the public offering price, less underwriting discounts and commissions. The Selling Stockholders will receive all of the proceeds from the offering. EngageSmart is not selling any of its shares in the offering and will not receive any of the proceeds from the sale of shares in the offering. The offering is subject to market and other conditions, and there can be no assurance as to whether or when the offering may be completed, or as to the actual size or terms of the offering.

Goldman Sachs & Co. LLC, J.P. Morgan, BofA Securities and Citigroup will act as joint book-running managers for the offering.

The public offering is being 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 preliminary prospectus supplement and accompanying prospectus relating to and describing the terms of the offering will be filed with the SEC and will be available on the SEC’s website at www.sec.gov. When available, copies of the preliminary 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.

Forward-Looking Statements

Certain statements in this release are “forward-looking statements” within the meaning of the Private Securities Litigation Reform Act of 1995. All statements other than statements of historical facts contained in this release may be forward-looking statements, including statements relating to the offering, including the timing and size of the offering and the grant of the option to purchase additional shares. In some cases, you can identify forward-looking statements by terms such as “may,” “will,” “should,” “expects,” “plans,” “anticipates,” “could,” “intends,” “targets,” “projects,” “contemplates,” “believes,” “estimates,” “forecasts,” “predicts,” “potential” or “continue” or the negative of these terms or other similar expressions. The forward-looking statements in this release are only predictions. EngageSmart has based these forward-looking statements largely on its current expectations and projections about future events and financial trends that EngageSmart believes may affect its business, financial condition, and results of operations.

Forward-looking statements involve known and unknown risks, uncertainties and other important factors that may cause EngageSmart’s actual results, performance or achievements to be materially different from any future results, performance or achievements expressed or implied by the forward-looking statements, including, but not limited to, the important factors discussed in Item 1A of EngageSmart’s Annual Report on Form 10-K for the year ended December 31, 2022, and Forms 10-Q and 8-K subsequently filed with SEC. Such statements in this release are based upon information available to EngageSmart as of the date of this release, and while EngageSmart believes such information forms a reasonable basis for such statements, such information may be limited or incomplete, and such statements should not be read to indicate that EngageSmart has conducted an exhaustive inquiry into, or review of, all potentially available relevant information. These statements are inherently uncertain and investors are cautioned not to unduly rely upon these statements. EngageSmart qualifies all of its forward-looking statements by these cautionary statements. Except as required by applicable law, EngageSmart does not plan to publicly update or revise any forward-looking statements contained in this release, whether as a result of any new information, future events, or otherwise.

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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