The early work experiences of a nationally representative sample of youth with severe disabilities (i.e., intellectual disabilities, autism, multiple disabilities) were examined. Using data from the National Longitudinal Transition Study-2, we explored the extent to which various student-, family-, school-, and community-level factors were associated with paid work experiences during high school. Findings highlight the elusiveness of early work experiences for many youth with severe disabilities and call attention to malleable factors that may play a role in shaping employment success during high school. Recommendations for research and practice are highlighted.