Bob Bennett, CEO at EngageSmart | Episode 161

What does an avid Squash player with an underdog mentality and a passion for sales have to do with payments? A lot! My guest this week is Engagesmart CEO Bob Bennett. He has run four different companies over the last 30 years and been in the payments ecosystem long enough to acquire a passion for the electronic payments industry and a desire to create differentiation within that space.

For those of you who may not know, Engagesmart is a bill presentment company that simplifies customer and client engagement through electronic payments. They own 4 different brands serving health and wellness, utilities, healthcare, and fundraising, all of which drive a digital self-service and payments experience. Their goal is 100% paperless and autopay solutions for invoice management and their proprietary brand Invoice Cloud drives their customer base at a rapid pace.

If you were to ask Bob what got him from an applied math and computer science degree to a prolific CEO in the payments space, he will be the first to tell you that sales became his calling at a young age and he “got really good at selling hard things.”

Tune in this week to hear Bob talk about his journey to becoming CEO, including his highly prescriptive method for hiring, recruiting, and retaining employees, his desire to create a unique SaaS business and his personal/professional “grow or die” philosophy. We also discuss the overall impact of the global pandemic and the tailwinds Engagesmart is still riding as a result of it.