Coach Woolf graduated from Kirkwood High School (St. Louis, MO) in 2001. While in high school he played football, basketball, and baseball. Coach Woolf was 2nd team all-conference linebacker in football and honorable mention guard in basketball his senior year.

After high school, Coach Woolf played football at Missouri State for one year, then transferred to Westminster College, where he played four years of football and two years of basketball. Coach Woolf graduated from Westminster College in 2006, where he then began his coaching career.

Upon graduation from Westminster College, Coach Woolf returned to his high school alma mater serving 11 years as football coach, where teams went to three state championships, winning in 2012 and 2016. He also served six years as the men’s basketball team coach and three years as the women’s basketball team assistant coach. The three years Coach Woolf served with the women’s basketball team they went to the state championship twice, winning in 2016. In 2018 Coach Woolf moved to North Carolina where he accepted a teaching and coaching job at Athens Drive High School here in Wake County. In the 2018-2019 season, Coach Woolf served as the Assistant Varsity Coach for the men’s basketball team finishing the season as conference champions.

Coach Woolf is Head Coach for both the Varsity Football team and the Varsity Women's Basketball team. Coach Woolf is also a teacher in our Intervention department here at Green Level High School. Off the court, Coach Woolf enjoys spending time with his family, working out, and hanging out with friends.