Robert P. Bennett
Chief Executive Officer
Bob is the founder and CEO of EngageSmart, which he launched in 2020. He has over 30 years of experience in technology, working with everything from computer software to payments to appliances. Bob founded his first company, MicroFridge, Inc., in 1988, and went on to other technology leadership positions, including as President of Sage Payments, before founding InvoiceCloud in 2009. Throughout his career, Bob’s focus on technological innovation, honest competition, and servant leadership have remained constant.
Bob loves his family, working, socializing and playing squash. He can be a bit competitive and believes it’s related to growing up in a large New England family, “You have to have lived through long winters with lots of brothers and sisters to truly understand it. Go Sox!”
Chief Legal Officer
Scott serves as EngageSmart’s Chief Legal Officer with responsibility for legal and regulatory functions. A seasoned legal, security, and compliance executive with deep public tech company experience, Scott has held chief legal officer roles at organizations including Carbonite, Intralinks, Novell, and TeleAtlas, NL. As a member of the Board of Directors for both the Disability Law Center of Massachusetts and the New England Village, he is passionate about working with and supporting members of the disability community.
Scott holds a J.D. from New England Law and an undergraduate degree from Boston University. Scott lives in Plymouth, MA and is an avid sailor and mountain biker.
Executive Vice President
Corporate Development And Strategy
Alan serves as EngageSmart’s Executive Vice President of Corporate Development and Strategy. Prior to joining EngageSmart, Alan spent fourteen years in the investment banking industry, specializing in ecommerce, retailing technology, payments, and broader fintech, first at Goldman Sachs and then at a boutique he co-founded and later led as its Managing Partner. He more recently spent seven years at Salesforce in product leadership roles, first on Salesforce’s enterprise commerce platform and then leading the build and launch of Salesforce Payments.
A lawyer by training, he holds a JD from Harvard Law School, an MA from Yale University, and an AB from Princeton University. Alan lives outside Boston with his wife and two children.
President, Enterprise Solutions
Kevin serves as President, Enterprise Solutions, including InvoiceCloud, Donor Drive and HealthPay24. Prior to joining EngageSmart, Kevin was the Divisional Vice President and General Manager of the Product Lifecycle Management (PLM) segment at PTC. In this role, Kevin is responsible for PTC’s strategy, product, go-to-market and customer success for PLM offerings including Windchill and ThingWorx Navigate. Previously at PTC, Kevin led the build out of PTC’s award- winning Internet of Things and Augmented Reality partner ecosystems.
Kevin also spent a decade at Oracle in a series of global go-to-market leadership roles building several new growth businesses. Kevin holds an MBA in General Management from Harvard Business School and a B.A. in Government from Colby College. He loves spending time with his wife and four kids and enjoys skiing, mountain biking, cooking and reading.
Chief People Officer
Kristen has worked within the People Function for the past 20+ years. Prior to EngageSmart, she served as CarGurus VP People & Talent. Kristen previously held senior-level HR leadership roles at HubSpot and Endeca. Through her career, Kristen has focused her efforts on start-up companies to build infrastructure around HR/recruiting operations and business expansion. She holds a Bachelor of Science from Westfield State University.
Kristen has a 2-year-old daughter. She loves the beach, golfing and New England sports (especially the Bruins and Patriots).
Chief Financial Officer
Cassandra joined EngageSmart in 2020 and serves as the company’s CFO. She most recently served as the Chief Accounting Officer and VP of Finance for Carbonite, Inc. which was sold to OpenText in December 2019, where she had direct responsibility for all aspects of the corporate finance function including FP&A, accounting, revenue operations, internal audit, tax and treasury. She is a results-driven corporate finance executive with deep experience in building, leading and advising companies through rapid growth, capital markets transactions, international expansion and M&A activity.
Cassandra lives in Lakeville, MA with her husband and two children and enjoys running in her free time.
President, SMB Solutions
Jonathan serves as President of EngageSmart SMB solutions, including SimplePractice and its ecosystem of products. Jonathan joined EngageSmart in 2019 as Executive Vice President Business and Corporate Development and managed EngageSmart’s strategic business initiatives, M&A, and integration activities. Prior to joining EngageSmart, Jonathan served as CFO and Head of Corporate Development at CLEAResult Consulting Inc., the largest outsourced implementer of demand response and energy efficiency customer engagement programs to North American electric and gas utilities.
Prior to CLEAResult, Jonathan has broad corporate finance experience with KRG Capital Partners, a middle-market private equity firm and investment banking at Wachovia Securities and Piper Jaffray.
Chief Of Staff
Barry serves as EngageSmart's Chief of Staff. Barry joined the company in 2014 to lead business development for InvoiceCloud. Prior to joining the InvoiceCloud, Barry served as the Director of Initiatives with Harris Computer where he was instrumental in building a network of fully integrated payment processing partnerships serving the government and utility marketplace. He has 30 years of government ERP experience.
Barry’s passions include his faith, family, friends and a regular contentious game of pickup basketball. When most discover that he is a proud Southern Illinois University Saluki, two consistent questions are posed; “you actually graduated” and “what’s a saluki”!
Chief Marketing Officer
As CMO of EngageSmart, Alison leads all aspects of marketing. Prior to joining EngageSmart in 2020, Alison spent five years as SVP Marketing at LogMeIn where she played a key role in the company’s rapid growth and expansion to become one of the industry’s leading SaaS organizations. Alison joined LogMeIn from Oracle where she held leadership positions in Oracle’s applications business, following Oracle’s acquisition of Endeca. Alison has a track record for building high-performing Marketing teams with decades of go-to-market experience from small private organizations to the world’s largest technology providers.
Alison splits time between Sunapee, NH and So. Dartmouth, MA with her husband and two teenagers.
Chief Technology Officer
Frank Laura joined EngageSmart in August of 2019 as the Chief Technology Officer. Frank’s role is well-matched for his experiences at building, leading, and improving high-performing technology teams, processes, and cultures in fast-growth companies. He brings decades of knowledge, skill, and perspective from his leadership roles in public and private companies like Quicken Loans, Progressive Leasing, and Aaron’s.
While technology has been in his blood from childhood, Frank has grown a greater passion for his wife and two sons. He enjoys outdoor leisure activities like mountain biking, cycling, skiing, fishing, boating, and ATV’ing.