Upon graduating from law school, Dreiband served as a law clerk to Judge William J. Bauer of the United States Court of Appeals for the Seventh Circuit. Following his clerkship, Dreiband served in the Independent Counsel's office for the Whitewater controversy. After a stint in private practice, Dreiband served in the administration of George W. Bush as deputy administrator of the United States Department of Labor's Wage and Hour Division (WHD) from 2002 to 2003 and as general counsel of the Equal Employment Opportunity Commission from 2003 to 2005. He again returned to private practice in 2005 and joined Jones Day in 2008.