Yesway Taps Rival CTO to Lead Tech Overhaul

Convenience store operator Yesway has hired Robert Hampton, the former technology chief at competitor Jacksons Food Stores, as its new Chief Technology Officer. The move signals a strategic pivot from aggressive expansion to a much-needed technological modernization after a period of stalled growth.

• An overdue upgrade: The executive shake-up comes as Yesway’s growth has stalled, according to analysis from C-Store Dive. It’s a necessary move for a company whose most recent tech headline was a loyalty program update from two years ago, positioning the nearly 450-store chain to compete in an industry defined by a digital "arms race."

• The turnaround artist: Hampton is a well-known figure in retail technology. During his nearly ten-year run at Jacksons, he oversaw the integration of over 120 stores and was a key player in launching the ExtraMile brand. He’s also known for championing the use of AI in the convenience store space.

Hampton is tasked with building a new technology vision from the ground up. This hire isn't just about updating systems; it's about re-architecting the company's digital foundation to support future scale and innovation. ampton's hire is part of a broader executive shake-up at Yesway. The move to bolster its tech leadership comes as the company is reportedly weighing a potential IPO or sale, and as the entire convenience store industry grapples with major technology trends for 2026.