Cunningham arrives from USAA, where he oversaw military affairs strategy and served as a bank strategy director. His career includes advisory roles at McKinsey & Company and positions at JPMorgan Chase and Zions Bancorporation. Jill Castilla, CEO of Citizens Bank of Edmond, noted that Cunningham’s ability to align technology and strategy with a mission-first mindset was key to his selection.
Beyond his corporate experience, Cunningham brings a track record of scaling veteran-focused initiatives, including his previous work at Military.com and the U.S. Chamber of Commerce’s Hiring Our Heroes program. At Citizens and ROGER, he will focus on scaling operations and developing new services for military personnel and the broader community. A graduate of Harvard Business School, Cunningham began his career as an Airborne Cavalry Scout in the U.S. Army.




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