Board of Directors

Paul G. Stamas has served as chairman of our board of directors since 2019.

Mr. Stamas is a Managing Director at General Atlantic, a global growth investment firm, where he also serves as Co-Head of General Atlantic’s financial services sector. Prior to joining General Atlantic in 2010, Mr. Stamas was an Associate at Welsh, Carson, Anderson & Stowe, concentrating on investments in the healthcare services and information & business services sectors. Prior to that, he was an analyst in the Consumer Retail Group in the Investment Banking division at Goldman Sachs.

Currently, Mr. Stamas currently serves on the board of directors of Creative Planning and SigFig, and he previously served on the board of directors of Insurity and Optionshouse. He also serves on the board of directors of the Harvard Business School Club of New York. Mr. Stamas holds a Bachelor of Science and Engineering in Operations Research & Financial Engineering from Princeton University and a Master of Business Administration from Harvard Business School.

Robert P. Bennett has served as our Founder, Chief Executive Officer and as a member of our board of directors since 2019.

Prior to serving in these roles, Mr. Bennett served as Chief Executive Officer of Invoice Cloud, Inc., the predecessor of EngageSmart and a current subsidiary of EngageSmart since 2009. From December 2001 to 2008, he served as the President of Sage Payment Solutions. Prior to his time at Sage, and since he formed his first business, MicroFridge, Inc,, Mr. Bennett has served in senior leadership roles, MicroFridge, Inc. Since 2011, Mr. Bennett has also served on the board of directors of Walpole Cooperative Bank. Mr. Bennett holds a Bachelor of Arts in Applied Math and Computer Science from the University of Maine and a Master of Science in Engineering Management from Northeastern University.

Deborah A. Dunnam has served as a member of our board of directors since 2021.

Ms. Dunnam is the Chief Commercial Officer at Dropbox, Inc., a provider of cloud based file hosting services. Prior to joining Dropbox, Ms. Dunnam served as Chief Operating Officer of ServiceSource from 2018 to 2020 and as Corporate Vice President of Inside Sales at Microsoft from 2016 to 2018. Prior that, she also held various senior roles at Cisco Systems, including serving as Senior Vice President of Worldwide Services Sales and Global Customer Success. Ms. Dunnam holds a Bachelor of Business Administration in Marketing and Social Science from Northwood University.

Matthew G. Hamilton has served as a member of our board of directors since the inception of EngageSmart.

Previously, Mr. Hamilton had served on the board of InvoiceCloud, LLC since April 2015. Mr. Hamilton is also a Managing Director at Summit Partners (“Summit”), a private equity firm, where he has served in various roles since 2005. Mr. Hamilton also serves on the board of directors of a.k.a. Brands, Snap Financial, Patriot Growth Insurance Services, Frontline Advance, Quay Eyeware, Adviser Investments and Forma Brands. Mr. Hamilton holds a Bachelor of Arts in Economics from Colby College.

David Mangum has served as a member of our board of directors since 2019. Mr. Mangum has also served as a Senior Advisor at General Atlantic, a global growth investment firm, since 2019.

Prior to joining General Atlantic, Mr. Mangum was President and Chief Operating Officer of Global Payments Inc., where he served in various roles since 2008. While at Global Payments, Mr. Mangum lead their transformation from a payment processor to a technology services and software company. From 2007 to 2008, he served as Executive Vice President, Fiserv Corp., a financial services technology provider which acquired CheckFree Corporation, provider of financial electronic commerce solutions in 2007. Mr. Mangum was also Executive Vice President and Chief Financial Officer of CheckFree Corporation from 2000 to 2007 and its Senior Vice President, Finance and Accounting, from 1999 to 2000. Mr. Mangum served on the board of directors of Thunder Bridge Acquisition II, LTD., a blank check company, from 2019 to 2021.

Currently, Mr. Mangum serves on the board of directors of Thunder Bridge Capital Partners III Inc., a blank check company, a role he has held since 2020 and of Thunder Bridge Capital Partners IV, Inc., a blank check preferred company, a role he has held since 2021. He also serves on the board of directors of Nextech, an EHR and practice management solution for specialty providers, a role he has held since 2020. Mr. Mangum holds a Bachelor of Arts in Political Science from Carleton College.

Preston McKenzie has served as a member of our board of directors since 2019. Mr. McKenzie has also served as Operating Partner at General Atlantic since 2019, after serving as a Special Advisor from 2017 to 2018.

Prior to joining General Atlantic, Mr. McKenzie served as Chief Executive Officer of NEWSCYCLE Solutions from 2013 to 2017, and Chief Executive Officer of MicroEdge from 2010 to 2013. Prior to that, he also held various senior roles at Thomson Reuters, including serving as Vice President and General Manager of their Business Development division. Mr. McKenzie also serves on the board of directors of Ethisphere and formerly served on the board of directors of Insurity and Mi9 Retail. Mr. McKenzie holds a Bachelor of Arts in Journalism from the University of North Carolina and a Master of Business Administration from the University of Minnesota.

Raph Osnoss has served as a member of our board of directors since 2019. Mr. Osnoss currently serves as a Managing Director at General Atlantic and focuses on the firm’s investments in the financial services sector.

Prior to joining General Atlantic, Mr. Osnoss was an Associate at Berkshire Partners, a private equity firm, from 2010 to 2012. Previously, he was also an analyst in the Investment Banking Division of Goldman Sachs from 2008 to 2010. He currently serves on the boards of Amount, Inc., a banking and loan origination software provider, Alkami Technology, Inc., a cloud-based digital banking platform, and Avant, LLC, a financial technology company. He previously served on the board of directors of Insurity, Inc, a cloud-based solutions and data analytics company. He also serves on the board of Edible Schoolyard NYC, a food and education-focused charitable organization. Mr. Osnoss holds a Bachelor of Science in economics from the Wharton School at the University of Pennsylvania and a Master of Business Administration from Harvard Business School.

Diego Rodriguez has served as a member of our board of directors since 2022.

Most recently, Mr. Rodriguez was Executive Vice President, Chief Product and Design Officer at Intuit. He guided the strategy, design, and delivery of Intuit’s AI-driven customer experiences and led its product management and design teams. Before Intuit, Mr. Rodriguez was a Senior Partner at IDEO. He was the Managing Director of IDEO Bay Area and developed Business Design as a core part of IDEO’s offer. As Global Managing Director of IDEO Futures he managed the creation of growth ventures, and funded and incubated a portfolio of external startups. At the start of his career Mr. Rodriguez developed leading-edge products as an engineer at HP and IDEO, and later marketed the pioneering online version of QuickBooks. He holds multiple patents.

Mr. Rodriguez served on the Harvard University Board of Overseers and as an Entrepreneur-in-Residence at Harvard Business School. He is a founding faculty member of the Hasso Plattner Institute of Design at Stanford (aka "the d.school"). Mr. Rodriguez is currently a Global Advisor to Harvard Business School and a Professor of the Practice at Boise State University.

Among Mr. Rodriguez’ accolades is a Chicago Athenaeum Good Design Award. Fortune named him one of “The Smartest People in Tech” and Fast Company called his writing “a must-read for anyone who wants to incorporate design thinking into their work.”