Yesway’s Former Senior Loyalty Manager Joins Rovertown

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Michael Caldwell, Customer Success Manager - Enterprise

Michael Caldwell has joined the team as its new Customer Success Manager - Enterprise. Amidst rapid growth in enterprise organizations choosing Rovertown’s app platform to power their digital engagement experiences, the company saw the need to further enhance its industry-leading customer success reputation. Caldwell joins Rovertown from Yesway, where he built and grew its award-winning loyalty program from 35 stores to more than 435 stores—and earned a reputation as an innovator in the industry.

“I’ve known the Rovertown team for several years, and I’ve always admired the work they’ve done to move our industry forward,” says Caldwell. “It’s so important for the digital experience to match a brand’s reputation and give customers that same ‘feel good’ feeling they get when they walk through the door. I’m thrilled to leverage more than seven years of experience at Yesway to serve our enterprise clients and enhance the customer-first approach that has made Rovertown so successful.”

After joining Yesway in 2017, Caldwell built and quickly grew Yesway Rewards into one of convenience retailing’s most successful and innovative loyalty programs. Following Yesway’s 2019 acquisition of the world-famous Allsup’s brand, Caldwell incorporated its more than 300 stores, giving them their first-ever loyalty program and unveiling the even more powerful Yesway & Allsup’s Rewards. Prior to joining Yesway, Caldwell spent nearly six years at Margaritas Management Group, a family-owned restaurant company with more than 20 Mexican restaurants, where he also built a successful rewards program.

At Rovertown, Caldwell will leverage his unique experience and skillset to establish a customer success program built specifically for the needs of enterprise clients. This comes at a crucial moment in Rovertown’s history as many enterprise retailers have chosen to join the Rovertown App Platform to level-up their digital store experience. Today’s news also comes on the heels of several notable hires, including the recent announcements of Tyler Cameron, formerly of MAPCO, as Rovertown’s Head of Strategy and Analytics, and Chris Patton, formerly of PAR Retail (Punchh), as Rovertown’s Head of Integrations and Implementations.

“When retailers can turn to former retailers for support, that sends a powerful message about a company’s dedication to customer success,” says Jeffry Harrison, President and Co-Founder of Rovertown. “Michael Caldwell is a well-regarded leader in our industry, and the impact he made at Yesway is nothing short of incredible. We’re thrilled for him to join the Rovertown team and work side-by-side as an advocate for our largest customers.”

Caldwell will make his debut in the signature blue Rovertown polo at PDI Connections Live in Washington DC from August 25-28. From October 7-10, he will also be one of the smiling faces in Rovertown’s booth at the NACS Show in Las Vegas.