Oliver founded Center for Competitive Democracy in 2005 after graduating from the Boston University School of Law. He is a member of the bar in Massachusetts and the District of Columbia and has been admitted to practice before several federal courts, the 3rd, 6th, 7th, 8th, 9th, 11th and D.C. Circuit Courts of Appeal, and the Supreme Court of the United States of America.

​He is author of “Death by a Thousand Signatures: The Rise of Restrictive Ballot Access Laws and the Decline of Electoral Competition in the United States,” published by the Seattle University Law Review, and he has also written for Counterpunch and the Philadelphia Inquirer.