Prior to joining the Bonner Foundation, Bobby worked at the Telesis Corporation, an affordable housing developer in Washington, D.C. He also served as managing director of the Campus Outreach Opportunity League (COOL) during its first three years of operation. In addition, for the past twenty years, Bobby has been associated in various capacities with the Youth Policy Institute, a Washington, D.C.-based non-partisan organization that researches and reports on policies and programs relating to young people.

Bobby received his bachelors degree from Harvard University in 1985 and a masters in public and private management from Yale University's School of Organization and Management in 1990.