Before joining Greens Farms Academy in 2018, Bob was Head of School for five years at Lake Forest Country Day School, a PreK-8 school serving more than 400 students in the suburbs of Chicago. Before his headship in Lake Forest, Bob was the Associate Head of School Rippowam Cisqua School in Bedford, New York, where he ran the Advancement Office, taught Ethics, writing, and coached basketball. Bob began his career in education at Brown University, where he served as the Director of the Parents Leadership Program after transitioning to education from several years as a touring singer/songwriter recording for Atlantic Records and EMI publishing.
Bob earned his B.A. from Brown University as a double major in American Civilization and Philosophy, and his M.Ed. in Education, Policy, and Management from Harvard University.