Kyle worked as casting associate and events manager for Music Theater Works, and rejoined the company in 2018 as producing artistic director, following a two-year stint in academia. He relocated to Chicago in 1999, after completing his Masters in Musical Theatre at Goldsmiths, University of London, where he produced and directed a workshop of new musicals. He also stage managed a series of new musicals with Perfect Pitch: New Musicals at Trafalgar Studios. In the Chicago area Dougan has directed, associate-directed and assistant-directed shows for Chamber Opera Chicago, Theatre at the Center, Big Noise Theater and The Music Theatre Company. He has served as artistic producer of a series of new musicals with Midwest New Musicals, as executive director of FWD Theatre Project and as co-owner of Style Theatrical Casting, a professional casting company in Chicago.