Bobb is a former appointed official who was the Emergency Financial Manager for the Detroit Public Schools until 2011.
In addition to having been employed by the school district, he received a salary from private foundations that promote school choice and privatization, and owns of a private/public sector consulting firm.Bobb's previous position was president of the Washington, D.C.
board of education from 2006 to 2009.
Before that he was the longest-serving African-American city manager in the United States, with a total of 30 years employment in the field.