Woolard held sports administration roles at
Washington State University starting in 1988. He remained there until May 2004, when he was hired as athletic director at the
University of South Florida. In January 2014, Woolard was reassigned from his role as athletic director, pending the expiration of his contract. Woolard retired from the University with an accelerating agreement in July 2014. In 2016, auditors named Woolard and other staff in reports of over-payment of 2014 salaries in possible violation of Florida law. ==Family==