Saylor's 25-year coaching career began at Loyall High School in 1942. After serving in the Army during World War II, Saylor returned to coaching at Wallins High School, his alma mater. Saylor went to Loyall High School in 1951 and served nine years as coach of the Indians. He then went on to Cumberland High School, leading the Redskins to a regional football title in 1963.
After leaving coaching, Saylor worked as an assistant principal at Evarts. He served one term as a state representative, and then went on to Wallins Elementary School as principal.
Saylor succeeded Mildred Rowland as superintendent of the Harlan County Schools in 1979 and served in the position until retiring in 1984.
In a story published in 2005, several of his former players recalled the impact Saylor had on their lives.
"I guess he's the reason I'm coaching today. He means a great deal to me," said John D. Wilson, a former player of Saylor's at Loyall who recently completed his 50th season in coaching. "What he did for me is still living and will last forever. If you do something for other people it never dies because they do something for somebody else. What you do for yourself doesn't last long. It dies with you. What he has done for others in coaching will go on for eternity."