CORRECTING and REPLACING Port St. Lucie and InvoiceCloud Launch New Online Payment System to Offer Customers Increased Self-Service Options

Please replace the release with the following corrected version due to multiple revisions.

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PORT ST. LUCIE AND INVOICECLOUD LAUNCH NEW ONLINE PAYMENT SYSTEM TO OFFER CUSTOMERS INCREASED SELF-SERVICE OPTIONS

The City of Port St. Lucie has implemented InvoiceCloud, an EngageSmart (NYSE: ESMT) solution for online bill payment services, to launch a new digital payment, customer engagement, and billing system for utility customers. The new payment portal went live on December 13, 2022.

With InvoiceCloud, the Port St. Lucie Utility Department offers its more than 90,000 customers a simpler and more intuitive payment solution. Customers now have the option to pay their utility bills via digital wallet, PayPal, Venmo, and text. InvoiceCloud’s solution also offers many additional self-service options like AutoPay, one-time payments, and paperless billing, allowing customers the flexibility to pay their utility bills in the way most convenient for them. The new system integrates directly with the City’s Infinity Customers Information System (CIS) from Advanced Utility Systems, and the Port St. Lucie mobile app, on which customers can pay their bills through InvoiceCloud.

Port St. Lucie began conducting all utility department services virtually in 2020 and has remained fully virtual ever since. According to an InvoiceCloud survey conducted in October of 2022, 50% of bill payers surveyed indicated that since the start of the COVID-19 pandemic they are now more likely to make a digital payment than they were before the pandemic started. InvoiceCloud’s solution will further drive e-adoption and improve their customers’ payment experience.

“Our team loves the fact that InvoiceCloud uses every possible touchpoint to drive customers to self-service,” said the City of Port St. Lucie’s Manager of Utility Billing and Connection Support, Regina Linsley. “Our customers want to manage their utility bills themselves online, and InvoiceCloud is designed to make every interaction with our portal simple and delightful.”

InvoiceCloud’s real-time data transfer ensures quick payment processing speeds and helps Port St. Lucie employees save time that can be better spent on other high-value projects. Lags in payment processing had historically prevented employees from doing other work and sometimes resulted in late payment notices for customers. Additionally, the City believes that InvoiceCloud’s high-adoption platform will drive more customers to self-service routes, saving the Utility Department a significant amount of money annually.

To take advantage of these new bill management and payment options, Port St. Lucie customers can enroll on the InvoiceCloud portal here.

About Port St. Lucie:

The City of Port St. Lucie is proud to be a hometown where people live, learn, work and play and celebrate all of life’s opportunities. With 224,905 residents, Port St. Lucie is Florida’s seventh largest city by population (South Florida’s third largest city). The City occupies an area of 120 square miles in St. Lucie County on Florida’s east coast, about 50 miles north of West Palm Beach, halfway between Miami and Orlando. The City provides most traditional municipal services including law enforcement, water and sewer and public works. For more information, please visit www.cityofpsl.com.

About InvoiceCloud:

InvoiceCloud, an EngageSmart solution, is a leading provider of online bill payment services. Founded in 2009, the company has grown to be one of the leading disruptors in the cloud-based electronic bill presentment and payment (EBPP) space, helping institutions put customer experience first. By switching to InvoiceCloud, clients can improve customer engagement, loyalty, and efficiency while reducing churn and missed payments in the process. To learn more, visit www.InvoiceCloud.com.

About EngageSmart:

EngageSmart is a leading provider of vertically tailored customer engagement software and integrated payments solutions. At EngageSmart, 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 (“SaaS”) vertical solutions, including SimplePractice, InvoiceCloud, HealthPay24 and DonorDrive, that are designed to simplify our customers’ engagement with their clients by driving digital adoption and self-service. As of September 30, 2022, EngageSmart serves 94,500 customers in the SMB Solutions segment and 3,300 customers in the Enterprise Solutions segment across several core verticals: Health & Wellness, Government, Utilities, Financial Services, Healthcare and Giving. For more information, visit www.engagesmart.com and follow us on LinkedIn.

About Advanced Utility System

Advanced Utility Systems is a subsidiary of Harris Computer Systems, providing Customer Information and Billing solutions exclusively to municipal, investor owned, and cooperative utilities established in 1997. With more than 150 successful customer deployments across North America, Central America, South America and the Caribbean, Advanced has the experience required to deliver a successful implementation of your mission critical CIS.

Forward-Looking Statements

Certain statements about EngageSmart’s business in this release are “forward-looking statements” within the meaning of the Private Securities Litigation Reform Act of 1995 and are based on current expectations and assumptions that are subject to risks and uncertainties. All statements contained in this news release that do not relate to matters of historical fact should be considered forward-looking statements, and are generally identified by words such as “expect,” “intend,” “anticipate,” “estimate,” “believe,” “future,” “could,” “should,” “plan,” “aim,” and other similar expressions. These forward-looking statements include, but are not limited to, statements regarding the anticipated benefits and use of the InvoiceCloud platform and other statements that are not historical facts. These forward-looking statements are neither promises nor guarantees, but involve risks and uncertainties that may cause actual results and events to differ materially from those contained in the forward-looking statements. Actual results and events could differ materially from those anticipated in these forward-looking statements for many reasons, including, but not limited to, the following: our inability to sustain our rapid growth; failure to manage our infrastructure to support our future growth; our risk management efforts not being effective to prevent fraudulent activities; inability to introduce new features or services successfully or to enhance our solutions; inability to achieve or sustain profitability; failure to adapt and respond effectively to rapidly changing technology, evolving industry standards and regulations and changing business needs, requirements or preferences; real or perceived errors, failures or bugs in our solutions; intense competition; lack of success in establishing, growing or maintaining strategic partnerships; COVID-19 pandemic and its impact on our employees, customers, partners, clients and other key stakeholders; legal and regulatory risks; and technology and intellectual property-related risks, among others. Other important risk factors that could affect the outcome of the events set forth in these statements and that could affect EngageSmart’s operating results and financial condition are discussed in Item 1A of our Annual Report on Form 10-K for the year ended December 31, 2021 and our Form 10-Q for the quarter ended September 30, 2022, as updated by our future filings with the Securities and Exchange Commission. Such statements are based on EngageSmart’s beliefs and assumptions and on information currently available to EngageSmart. EngageSmart disclaims any obligation to publicly update or revise any such forward-looking statements as a result of developments occurring after the date of this document except as required by law.

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