Robert Stephenson graduated from Ohio State University, Moritz College of Law. While in law school Mr. Stephenson served as member of the National Moot Court Team, Associate Justice of the Moot Court and Lawyering Skills Governing Board, Assistant Director of the Appellate Advocacy Counsel, and Associate Member of the Pro Bono Research Group.

Robert Stephenson clerked in the Criminal Appellate Division of the United States Attorney's Office, served as a Judicial Law Clerk to the Honorable Dennis P. Moroney in the Milwaukee Circuit Court, as a Judicial Extern to Ohio Supreme Court Justice Deborah Cook, and worked as a Judicial Law Clerk for the Honorable Peggy Bryant of the 10th District Court of Appeals in Columbus, Ohio. Upon relocating to Oak Park, Illinois, Mr. Stephenson served as Assistant Defender in the Office of the State Appellate Defender where he represented clients before the Illinois Appellate and Supreme Courts.

In addition, Robert Stephenson served eight years in the United States Army Reserves, receiving an Honorable Discharge in 1997, worked as legislative assistant to Oregon State Senator Randy Miller, and was appointed by Governor John Kitzhaber to the Oregon Employment Department Board of Advisors.