On this episode of The Cheers Pod, Drew sits down with Shripal Shah, Chief Digital Officer at Next League, to explore the future of fandom, loyalty, and the massive revenue upside hiding in plain sight.
Shripal’s career spans retail, tech, and sports. He’s led strategy and marketing for the Washington Commanders, served as Chief Digital Officer at Shop Your Way—the Sears and Kmart rewards platform—and now advises leagues and teams on how to transform fan engagement with modern digital tools.
He unpacks why so many loyalty programs have failed, how industries like airlines and hotels turned points into billion-dollar assets, and why sports teams are uniquely positioned to unlock similar value. From behavioral rewards that deepen everyday fan engagement to cutting-edge examples like the Cavaliers’ card-linked program with Plaid, Shripal explains how loyalty can drive 8–9 figure revenue lifts while creating stronger sponsor relationships and more personalized fan experiences.
If you’re in sports, eCommerce, or loyalty marketing, this episode offers a masterclass on turning emotion into measurable revenue and why now is the moment to modernize fan engagement.
