 Whipple served as the head football coach at University of New Haven from 1988 to 1993, Brown University from 1994 to 1997, and stints as the University of Massachusetts Amherst (UMass), from 1998 to 2003 and 2014 to 2018.His 1998 UMass team won the NCAA Division I-AA Football Championship.He was the quarterbacks coach for the Cleveland Browns of the National Football League (NFL) in 2011 and 2012.