Welcome back to the Paycast Network, where we dive deep into the world of fintech and payments with the veterans who built the industry from the ground up. In our latest episode, we sat down with Jesse Memmel, a man whose career trajectory is a masterclass in persistence, from the gritty days of telemarketing to the cutting edge of AI-driven point-of-sale technology. Jesse’s story is a reminder that the “overnight success” we see in the boardroom is usually preceded by thousands of doors knocked on and a complete refusal to entertain a backup plan.
From the Phone Books to the Boardroom
Jesse Memmel’s entry into professional sales wasn’t through a prestigious internship, but via a headset in a call center back in the early 2000s. He spent his early years grinding in telemarketing, selling everything from newspaper subscriptions to specialized services, before a business partner introduced him to Calpen and the world of credit card processing residuals. At the time, the industry was a different beast entirely, and Jesse built his foundation by carpooling to East Texas and literally walking every floor of every office building he could find. He vividly recalls his first deal—a complex mix of buy rates and surcharges that would baffle many modern agents—which proved that if you could navigate the math, you could build a career.
Building Residual “Stickiness”
After years of boots-on-the-ground sales, Jesse transitioned into the development side of the industry, though not without significant growing pains. He shared the candid story of a $600,000 setback when an attempt to develop software offshore resulted in a “bag of spaghetti” that had to be scrapped. Rather than folding, he regrouped to create Paradise POS, a venture that eventually led to a successful exit and cemented his reputation as a product visionary. Today, as the Chief Product Officer for Enrollment Pay and a board member for Snap Menu, Jesse’s philosophy centers on “stickiness”. He argues that because pricing has become a commodity, the only way to protect your residuals—the “bell cow” of the business—is to provide integrated value through loyalty programs, rewards, and advanced technology that makes it impossible for a merchant to leave for a slightly lower rate.
The AI Frontier and the “No Plan B” Mentality
Looking toward the future, Jesse sees a massive shift in how software is built and sold. He predicts that Artificial Intelligence will move us away from “one-size-fits-all” software boxes and toward hyper-personalized, niche solutions that are easier and cheaper to produce. Whether it’s software specifically for wineries, gun stores, or golf courses, the democratization of development means agents must become true technology consultants. Despite these high-tech shifts, Jesse’s core advice for the next generation remains strikingly simple: there is no Plan B. He believes that success isn’t found in a clever backup plan, but in the willingness to get off the couch and work 50 hours a week until your goals are met.
“If you have a backup plan, you’re making excuses already before you even get started.” — Jesse Memmel