This article offers considerations for principals and other educators as they seek to provide students with intellectual disabilities (ID) with authentic work placement experiences. Survey and interview data gathered from 20 employers, 7 paraprofessionals (job coaches), a principal, and 21 students with intellectual disabilities provide a triangulated perspective from which to view supported and successful work placements. These perspectives offer recommendations for coordinated, collaborative and belief-driven action on the part of high school principals that will enhance the opportunities for successful community engagement beyond high school for students with intellectual disabilities.