The expectations of parents can shape the post-school pathways of young people with intellectual and developmental disabilities (IDD). Yet little is known about how parents view the employment prospects and priorities of their sons and daughters after high school. We examined expectations, preferences, and concerns of 1,065 parents of children and youth with IDD (below age 22) related to outcomes after leaving high school. We found parents prioritized paid community employment over sheltered options, valued qualitative aspects of the workplace (e.g., personal fit and interaction opportunities) over common employment outcome metrics (e.g., pay and hours), and held substantial concerns about their child’s future employment success. We found that multiple factors shaped parental expectations and the extent to which their daughters or sons accessed early career development experiences. We offer recommendations for research and practice aimed at raising expectations for and access to community employment for young people with IDD.