Ross joined Westport Country Playhouse as managing director in February 2009. He served since 2002 as managing director of CENTERSTAGE in Baltimore, the award-winning State Theater of Maryland. Previously, Ross was managing director of Long Wharf Theatre (1997-2002), where he was on the producing team for the commercial transfer of the Pulitzer Prize winner, Wit. He was general manager, and business and box office manager at Hartford Stage (1986-1996). Ross served as program officer/project director at National Arts Stabilization, and worked with Baltimore Opera Company and Alley Theater, Houston. Ross has consulted in fundraising, board development and strategic planning for theaters nationwide, including Kansas City Repertory Theatre, SITI Company, Wilma Theater, Trinity Repertory Company and Eugene O’Neill Theater Center. He has been a panelist for programs hosted by the National Endowment for the Arts, Theatre Communications Group and New England Foundation for the Arts, among others, and was an adjunct professor in Yale University School of Drama Theater Management Program.