Andy Chiles

Andy Chiles, Senior Director of Athletics & Business Development

Mr. Andy Chiles began working at The First Academy in 2025. With an extensive background in athletic administration and a passion for developing student-athletes, Chiles brings a wealth of experience to The First Academy’s tradition of excellence.

Chiles most recently served as the Athletic Director at Winter Park High School and had been there since 2019. He previously served as the Athletic Director at Lake Nona High School from 2009 to 2019. He played a pivotal role in enhancing both school’s athletic programs. In addition to his leadership at the high school level, he has been a prominent figure in interscholastic athletics, serving as FHSAA Board of Directors President, President of the National Interscholastic Athletic Administrators Association (NIAAA), and currently holding the position of Executive Director for the Florida Interscholastic Athletic Administrators Association (FIAAA). His commitment to student-athlete development, program growth, and sportsmanship has earned him widespread recognition in the field of athletic administration.