Woolard held sports administration roles at Washington State University starting in 1988.
[1] Woolard was named athletic director at Saint Louis University in October 1994.
[2] He remained there until May 2004, when he was hired as athletic director at the University of South Florida.
[3] In January 2014, Woolard was reassigned from his role as athletic director, pending the expiration of his contract.
[5] In 2016, auditors named Woolard and other staff in reports of over-payment of 2014 salaries in possible violation of Florida law.