After clerking, in 1982, Gutman joined the Washington, D.C., law firm of Williams & Connolly LLP. He left the firm in 1985 to become Special Assistant to F.B.I. Director William H. Webster, focusing on counter-intelligence and counter-terrorism. Gutman rejoined Williams & Connolly in 1986, and in 1988, Gutman became a partner at the firm, where he focused on commercial litigation, including securities, contracts, antitrust, labor, banking, real estate, intellectual property, insurance coverage, international law, and partnership disputes.
