Crutchfield made his coaching debut at Omaha in the 1995-96 season. He then followed Omaha head coach Tim Carter to the University of Texas-San Antonio, where he served as an assistant coach for the Roadrunners from 1996-97. He earned his first head coaching role with Tyler Junior College, a position he held from 1999-01.
 
Prior to his coaching debut, Crutchfield played football and basketball at Omaha. He received his bachelor's degree in criminal justice in 1992 followed by his master's degree in health, physical education, and administration in 1996.
 
Crutchfield's wife Jodi is also an UNO graduate. They have three sons, Derrick, Jalen, and Josh.