Courtland has been practicing law for thirty-seven years and for twenty-eight years has been in independent practice as attorney for Robert D. Courtland, Chartered. Prior to forming Robert D. Courtland, Chartered, Courtland spent seven years at the IRS as Senior Tax Law Specialist in the Corporate Reorganization Branch, specializing in domestic and foreign corporate mergers and acquisitions. Courtland is licensed in Washington, DC and Maryland, having graduated with a J.D. from Georgetown University. His undergraduate degree is from Pennsylvania State University where he majored in Political Science and also studied English and History. Courtland is a frequent lecturer and former Adjunct Professor of Tax Law at Georgetown University.