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Robert P. Bennett

Robert P. Bennett

CHIEF EXECUTIVE OFFICER

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CEO of
EngageSmart
EngageSmart

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!”

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