[1] Woolf graduated from Preston High School (Idaho) in 1991, and then served a two-year church mission in Antwerp, Belgium[2] He graduated cum laude from Utah State University in 1997 with Bachelor of Arts in Political Science In 2006, while working full-time at the Idaho State Controller's Office, he earned a Master of Business Administration from Boise State University.
[2] After graduating from Utah State University he interned at the Idaho State Controller's Office, starting in 1997, and rose through the ranks serving as a training specialist, bureau chief, and division administrator over Statewide Payroll.
In 2011, he was appointed chief of staff for former State Controller Donna M. Jones.
Following Jones’ automobile accident in May 2012, Governor Butch Otter, at her recommendation, appointed him temporary acting State Controller.
[3] Following Jones' retirement on October 15, 2012, Woolf was appointed permanent State Controller to serve the remainder of her term which expired January 2015.