Conversations about improving employment outcomes for young people with severe disabilities have been pervasive in the field of special education since the concept of “transition” was first conceived more than 25 years ago (Will, 1984). Despite many hard-fought developments in the areas of legislation, policy, research, and practice, changes in the employment landscape for youth and young adults with disabilities have been strikingly slow and often uneven (Carter, Austin, & Trainor, 2012). Far too many young people with severe disabilities living in communities across the country still do not receive the encouragement, instruction, supports, and linkages they need to share their talents and relationships within the workplace.