Although entry into the world of work is a prominent marker of postschool success in the United States, students with severe disabilities often leave high school without the skills, experiences, and supports that lead to meaningful employment. The authors examined the extent to which an array of student, family, and school factors was associated with employment during the 2 years following high school. Having held a paid, community-based job while still in high school was strongly correlated with postschool employment success. In addition, being male and having more independence in self-care, higher social skills, more household responsibilities during adolescence, and higher parent expectations related to future work were all associated with increased odds of employment after school for young adults with severe disabilities. Implications for transition policy and practice are presented along with recommendations for future research addressing the career development of youth with intellectual disabilities, multiple disabilities, and autism.