Ross has worked in the fields of education and recreation for over 30 years. Ross holds a Bachelor of Science degree in both psychology and psychobiology from Hamilton College and a Master of Science degree from Villanova University, where he studied counseling and human relations. He began by working with emotionally disturbed children in local agencies outside of Philadelphia. After completing his graduate work, Ross spent 11 years working as a school counselor specializing in family counseling and crisis intervention.

Prior to moving to Richmond, Ross spent 23 years as a director of summer programs for two separate summer camp operations. As the director of a day camp with 200 children at a prominent independent school outside of Philadelphia, Ross built and developed a comprehensive, integrated summer program that included a general day camp, sports camps, specialty camps and academic enrichment programs. Building on the foundation of the original day camp, the program grew and evolved over 11 seasons into 12-15 separate programs with more than 1100 children. Ross then moved to a large, privately-owned, multi-faceted recreational facility that included a newly-established summer camp with an enrollment of only 185 campers. Ross was responsible for all facets of the program: personnel, budget, registration and enrollment, scheduling, marketing and business development, facilities, transportation and food service. Under his leadership, enrollment grew to 800 campers within four years and averaged over 600 campers per year during his 12-year tenure.