BackgroundSecure employment is associated with positive self-esteem and higher quality of life. People with autism spectrum disorder (ASD), however, have poor employment outcomes. Typically, school personnel provide vocational supports for students with ASD. By learning from school personnel’s experiences, we can understand what works well and inform future service development. AimsWe aimed to identify barriers and facilitators that school personnel consider when preparing youth with ASD for employment. MethodsTwenty school personnel participated in semi-structured interviews. ProceduresWe conducted thematic analysis to understand how school personnel approached employment preparation with this population. This analysis was guided by an occupational therapy transactional perspective. Outcomes and ResultsWe developed a conceptual model to highlight the transactions across contextual factors in employment preparation. School personnel viewed creating a meaningful life in the community and maintaining employment as inseparable. School personnel also highlighted the importance of empowering youth, supportive environments, and cooperative parents. Conclusions and ImplicationsIn preparing youth with ASD for employment, school personnel equally valued contextual factors, individual characteristics, and the dynamic relations between these elements. Future intervention and service development should be guided by a consideration of the transactions between individual and environment.