 Whipple began his coaching career as an assistant coach at St. Lawrence University in 1980, before serving as the offensive coordinator at Union College for next two seasons.In 1984, Whipple was hired as an assistant coach at his alma mater (Brown) where he worked with the wide receivers.The following season, Whipple spent as a member of the coaching staff for the United States Football League's Arizona Wranglers under George Allen, assisting with the quarterbacks.