Episode 240: Bob Bennett - Founder & CEO, EngageSmart

It’s very rare for a company to make it to the public markets. It’s even rarer to have the founder of the company as its CEO throughout the full lifecycle to that IPO milestone. EngageSmart provides vertically tailored customer engagement software and integrated payments solutions. The company went public back in September of last year and Bob had the honor of ringing the bell of the New York Stock Exchange as its CEO & Founder on a day when the stock had priced above its initial range as a publicly traded company. This was not Bob’s first company. He’s a serial entrepreneur, who was the founder of MicroFridge, a company that created a refrigerator-freezer-microwave appliance combo which was built for college dorm rooms and motels. The company scaled to millions of dollars in revenue and an acquisition, but as you’ll hear, Bob shares a powerful lesson from this experience that led to his future success. In this episode of our podcast, we cover: * Bob’s background growing up and the importance of having a chip on your shoulder. * The full story of MicroFridge and how they were able to create an innovative product in a very complex and competitive market. * How he gained expertise in the payment industry and what led him down the path of starting Invoice Cloud, an early SaaS / cloud company. * Scaling Invoice Cloud and acquiring other vertical solutions to the point of launching the overarching EngageSmart brand. * Advice on building a company’s culture as it scales. * And so much more. If you like the show, please remember to subscribe and review us on iTunes, Soundcloud, Spotify, Stitcher, or Google Play.