Bob Bennett, CEO at EngageSmart | Episode 161

05/09/22 • 32 min

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.

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Paul Hadfield, CEO at TRNXN | Episode 160

My guest this week has been in the payments industry for 20 years and credits the lifespan of his prolific career to a small decision that was motivated by an empty gas tank. It all started in the basement of a dental office, at a startup ISO space with no windows, and an inclination that maybe this wasn’t such a good idea. But he needed enough gas to get to where he was going next, so he decided to give it a chance and the rest is history.

TRNXN Company CEO Paul Hadfield has made it his charge to modernize payments for his clients and provide them with a “project design” that optimizes their potential and maximizes their revenue. According to him, “the point-of-sale is really the central nervous system of any business. It can manage and connect every single moving part of your company.”

For those of you who may not know, TRNXN is a modern transaction company that designs, implements, and supports custom payment solutions for the retail and restaurant verticals. It is Paul’s belief that in order to build successful ISOs and profitable payments companies today, you have to leverage technology and service. With this intention in mind, TRNXN Company “helps ISOs modernize their business by helping them modernize their client’s business.”

What’s their business model? According to Paul, they’re not just payment providers but rather small business consultants. “Anything that has to do with a financial transaction, we are involving ourselves with and trying to make that process easier or less expensive for the business – or more expensive but with a strategy that drives more sales.”
Tune in this week to hear Paul talk about TRNXN Company – A business with “no exit plan” that he intends to run for the rest of his life and represents “a combination of everything he has learned in the industry coming to a head.” We also talk about what payments looks like for the retail and hospitality industry over the next 2 to 3 years, including everything from a spike in QR code implementation, to the astronomical margins on the current delivery model, and how long it will take crypto to make it into the restaurant space. Don’t miss it!

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Larry Hipp, CEO at Brightwell | Episode 162

My guest this week started as a software engineer but soon discovered he had a love for payments. Brightwell CEO Larry Hipp has had a fascinating journey throughout the fintech space. He has a genuine passion for seeing people succeed and places a tremendous amount of intention and importance on the resiliency that a strong company culture can provide.

For those of you who may not know, Brightwell is a fintech company that grew up in the prepaid industry. They cater predominately to the cruise ship market by providing prepaid cards for employee payroll. In fact, it wouldn’t be a stretch to say that they single-handedly transformed the cruise ship industry from cash to digital.

So, how did the global pandemic impact their business model? It’s inspiring to hear how the company continued to survive and thrive when cruise ships around the world completely shut down.

Post-pandemic, they are going strong and have expanded their product suite into cross-border payments just as much as cruise ship payroll. One of their most coveted offerings, and a competitive advantage that truly sets them apart in the industry, is their capacity to have so many of the country’s top money movers under one roof. Their proprietary app interface features Western Union, MasterCard, MoneyGram, and several other key players to facilitate cross-border payments for their customers.

Tune in this week and hear Larry talk about his journey through fintech and where he sees the industry going in the next 2-3 years, including a predicted consolidation throughout the fintech space to create new versions of the legacy players and how blockchain will change our industry significantly.