Before joining the staff at Converse, served as the assistant coach at Earlham College in Richmond, Indiana. At Earlham, prior to the 2020 women’s lacrosse season being cancelled due to COVID-19, Woolard was responsible for overseeing the team’s defensive system, as well as developing practice plans and coordinating the prospective student-athlete days for the program. In addition, she created scouting reports for the team, conducted game film analysis, and managed the team’s social media accounts. Woolard also monitored the student-athletes’ academic progress and represented the department on institutional marketing committees.

During her two seasons at Ferrum, Woolard was the Panthers' assistant coach and defensive coordinator. She assisted with all aspects of the program including recruiting, practice planning, game film analysis, coordinating team travel, organizing summer camps, and mentoring student-athletes in both team matters and academics. Under Woolard's tutelage, three Ferrum players earned USA South All-Conference honors, with one All-Sportsmanship team selection. Three players were also tabbed with Intercollegiate Women's Lacrosse Coaches Association (IWLCA) academic honors during Woolard's stint at Ferrum.

Prior to her time at Ferrum, Woolard was the head coach at Hanover High School in Mechanicsville, Virginia, during the 2017 campaign. She led the Hawks to a 9-8 overall record with 14 players earning all-conference honors and four receiving the nod at all-region selections. She spent the 2014 through 2016 seasons as an assistant coach at Hanover and was the program's defensive coordinator.

Woolard played one season of collegiate lacrosse at Lynchburg College in 2013, before graduating with a Bachelor's degree in philosophy with a double minor in business and criminal justice from Virginia Commonwealth University in 2015.