After graduation, Casciola spent three years as the freshmen coach at his alma mater. He then joined the Princeton varsity coaching staff, where remained through the 1965 season. Casciola also served as an officer in the United States Army and attained the rank of captain before being discharged in 1965. From 1966 to 1968, he spent three years mentoring the defensive ends and linebackers at Dartmouth under head coach Bob Blackman from 1966 to 1968. From 1969 to 1970, he served as the defensive coach at Connecticut. In December 1970, he was promoted to head coach in place of John Toner, who remained at UConn as athletic director. Casciola led UConn to a 5–3–1 record in his first season and a share of the Atlantic 10 Conference championship. After one additional season at UConn, he amassed a record of 9–8–1 during his tenure.
In March 1973, Princeton appointed Casciola as its head coach and continued through 1977.
In 1987, he left his position with the First Fidelity Bank of New Jersey to take over as executive vice president and chief operating officer for the New Jersey Nets of the National Basketball Association. Casciola held that post for five years. In July 1991, Casciola resigned from the Nets to become the executive director of the National Football Foundation and College Football Hall of Fame. Upon being chosen for The National Football Foundation's Distinguished American Award in 2004, noted Sports Artist Ted Watts added one more accolade saying, "I think your most admirable trait is to have faith and vision beyond the chalk marks of a football sideline".
Casciola has four children with his wife, Janet.