Objective: The specific aim of this study was to use data from the National Longitudinal Transition Study-2 (NLTS-2) to examine modifiable factors that were related to competitive employment acquisition for students who were at high risk of poor school-to-work outcomes. Design: Quantitative descriptive design using path analysis. Participants: 580 students were identified as at risk of poor school-to-work outcomes through a prior study. Results: Logistic regression models indicate that the modifiable factors most closely related to employment were higher expectations for competitive employment on the part of the parents, higher levels of self-advocacy, and participation in some type of postsecondary education and training. Conclusion: Our findings indicated that postsecondary education and psychosocial interventions aimed at changing parental expectations and enhancing students' self-advocacy, self-efficacy should be considered for transition-age youth at risk of poor post-high school employment outcomes.