Bob Bennett is a sales-oriented generalist with extensive experience building leadership teams that create processes to drive sustainable, profitable growth. He currently serves as an independent board member of InvoiceCloud and SimplePractice, the two principal businesses that formed EngageSmart, after he retired from his role as CEO of EngageSmart in April 2024.
Bob originally cofounded InvoiceCloud, a leading web-based provider of electronic bill presentment and payment solutions, in January 2009, where he and his team drove aggressive organic growth and added smart private equity partners to support M&A. His efforts led to the creation of a parent company, EngageSmart, and the completion of an IPO in 2021.
Since retirement, Bob has become involved with organizations and programs in Boston, including EforAll, The Boston Foundation, and Northeastern University, to help bridge the wealth gap through entrepreneurship in disadvantaged communities. He is an active squash player, boater, sports enthusiast, and family man.
