EngageSmart’s Chief Financial Officer Awarded Gold for Female Executive of the Year Alongside EngageSmart’s Wins for Achievement in Both Finance and Work-Life Balance

EngageSmart Inc., (NYSE: ESMT), a leading provider of vertically tailored customer engagement software and integrated payments solutions, is the winner of the following Stevie® Awards in the 20th annual Stevie Awards for Women in Business:

• EngageSmart’s CFO Cassandra Hudson won Gold for Female Executive of the Year – Business Products – 11 to 2,500 Employees - Computer Software
• EngageSmart won Gold for Achievement in Finance
• EngageSmart won Bronze for Achievement in Promoting Work-Life Balance

The Stevie Awards for Women in Business honor the achievements of women executives, entrepreneurs, employees, and the companies they run worldwide. The Stevie Awards have been hailed as the world’s premier business award. Nicknamed the Stevies for the Greek word for “crowned,” the awards were presented to winners Friday night during a gala event attended by nominees and their guests at the Marriott Marquis Hotel in New York City. The event was broadcast via livestream.

More than 1,600 entries were submitted this year for consideration in more than 100 categories, including Executive of the Year, Entrepreneur of the Year, Company of the Year, Startup of the Year, Women Helping Women, and Women Run Workplace of the Year.

EngageSmart is a leading provider of vertically tailored customer engagement software and integrated payments solutions that serves over 119,600 customers in the Health & Wellness, Government, Utilities, Financial Services, and Giving spaces. EngageSmart’s solutions SimplePractice, InvoiceCloud, and DonorDrive are designed to help simplify customers’ engagement with their clients by driving digital adoption and self-service.

“It’s an honor for our Chief Financial Officer Cassandra Hudson and our women-led teams to be recognized by the Stevies—their dedication to our customers and commitment to our teams is essential to EngageSmart’s success,” said EngageSmart Chief Executive Officer Bob Bennett. “As an organization, we prioritize career development and cultivate an environment where our teams can thrive personally and professionally, and I am proud to work alongside these incredible women who lead by example.”

“In its 20th year, the Stevie Awards for Women in Business received an outstanding body of nominations from women in organizations of all types, in 26 nations,” said Maggie Miller, president of the Stevie Awards. “We are gratified by how meaningful it is to women to win a Stevie Award, and how impactful it can be on the futures of their careers and their organizations. We congratulate all of this year’s Grand, Gold, Silver, and Bronze Stevie Award winners for their achievements.”

Gold, Silver, and Bronze Stevie Award winners were determined by the average scores of more than 200 business professionals around the world, working on six juries. Details about the Stevie Awards for Women in Business and the list of 2023 winners in all categories are available at www.StevieAwards.com/Women.

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, and DonorDrive, that are designed to simplify our customers’ engagement with their clients by driving digital adoption and self-service. As of September 30, 2023, EngageSmart serves 116,200 customers in the SMB Solutions segment and 3,400 customers in the Enterprise Solutions segment across several core verticals: Health & Wellness, Government, Utilities, Financial Services, and Giving. For more information, visit www.engagesmart.com and follow us on LinkedIn.

Forward-Looking Statements

Certain statements 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 anticipated financial performance and financial position, including our financial outlook for the first quarter and full year 2023 and thereafter, 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 to differ materially from those contained in the forward-looking statements. Our actual results 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 attract new customers or convert trial customers into paying customers; inability to introduce new features or services successfully or to enhance our solutions; declines in customer renewals or failure to convince customers to broaden their use of 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; fluctuations in quarterly operating results; future acquisitions and investments diverting management’s attention and difficulties associated with integrating such acquired businesses; general economic conditions (including inflation and rising interest rates), both domestically and internationally, as well as economic conditions affecting industries in which our customers operate; the war in Ukraine; concentration of revenue in our InvoiceCloud and SimplePractice solutions; 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 the Company’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 subsequent Quarterly Reports on Form 10-Q, as updated by our future filings with the Securities and Exchange Commission (“SEC”). Such statements are based on the Company’s beliefs and assumptions and on information currently available to the Company. The Company 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.

Disclosure

We disclose information to the public concerning EngageSmart, EngageSmart’s products and services, and other items through a variety of disclosure channels in order to achieve broad, non-exclusionary distribution of information to the public. Some of the information distributed through these disclosure channels may be considered material information. Investors and others are encouraged to review the information we make public in the locations below.* This list may be updated from time to time.

*For information concerning EngageSmart and its products and services, please visit: www.engagesmart.com

*For information provided to the investment community, including news releases, events and presentations, and SEC filings, please visit: investors.engagesmart.com/overview/default.aspx

*For information provided to the media, including news releases, please visit: investors.engagesmart.com/news/default.aspx

*For additional information, please follow EngageSmart’s social media accounts: www.twitter.com/engagesmartinc, www.facebook.com/EngageSmartInc, and www.linkedin.com/company/engagesmart

About the Stevie Awards

Stevie Awards are conferred in eight programs: the Asia-Pacific Stevie Awards, the German Stevie Awards, the Middle East & North Africa Stevie Awards, The American Business Awards®, The International Business Awards®, the Stevie Awards for Great Employers, the Stevie Awards for Women in Business, and the Stevie Awards for Sales & Customer Service. A ninth program, the Stevie Awards for Technology Excellence, will debut in 2024. Stevie Awards competitions receive more than 12,000 entries each year from organizations in more than 70 nations. Honoring organizations of all types and sizes and the people behind them, the Stevies recognize outstanding performances in the workplace worldwide. Learn more about the Stevie Awards at http://www.StevieAwards.com.

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