Roberts began his teaching career in 2001 at Baltimore City Public Schools, where he worked as a teacher for five years, a resident principal for one year, and a principal for two years. During this time, he also attended Morgan State University from Fall 2002 to Spring 2007, pursuing a doctorate degree, though the university confirmed he did not complete the program.
Roberts' career then took him to several school districts, including the District of Columbia Public Schools, St. Louis Public Schools, Aspire Public Schools in Oakland, California. He later served as superintendent of Millcreek Township School District in Erie, Pennsylvania. Millcreek officials stated that all required clearances, including an FBI background check and an I-9 form, were completed during his hiring process. They also noted they had no information regarding any expiration of Roberts' work authorization.
In 2023, Roberts was hired by Des Moines Public Schools. At the time, the district announced that Roberts had earned a doctorate degree from Trident University, a private for-profit online institution. KCCI has reached out to Trident University to confirm this degree, but has not yet received a response.
