Boler joined Chicago Fire FC in 2010 starting in the Academy and then spending the last 10 years with the First Team in the Football Operations department. During that span, he was overseeing the day-to-day operations and was the first point of contact for first team players and coaches. He worked closely with Sporting Leadership developing operational strategies, tactics and benchmarks which saw the highest player transfers in Club history. Additionally, Boler was responsible for leading the Club’s compliance efforts for the League’s training and matchday guidelines. Prior to joining Chicago Fire FC, Boler played collegiately at Indiana University-Bloomington where he received his Bachelor’s degree in Sports Marketing & Management with a Business Minor.