Following a tour of duty in the United States Army as a first lieutenant (1960–1962), Ross found work coaching high school football. He coached at Colonial Heights High School, and at his own nearby alma mater of Benedictine, both located near Richmond, Virginia. He then moved on to coaching at the college level, starting with assistant coaching stints at William & Mary, Rice, and Maryland before accepting his first head coaching job in 1973 at The Citadel, The Military College of South Carolina, located in Charleston, South Carolina.