Introduction: Youths with visual impairments attend postsecondary school at high rates, yet these individuals have low rates of employment. In this study, factors associated with post-school employment were investigated in a nationally representative sample of youths with visual impairments. Methods: In a secondary analysis of data from the National Longitudinal Transition Study-2, multivariate logistic regression analyses were conducted to investigate employment outcomes for youths with visual impairments based on orientation and mobility skills and outcome expectations. Results: Youths with high community travel scores were significantly more likely to be employed in Wave 4 (up to six years post-high school; B = 0.25, p = 0.003) and those with high outcome expectations were significantly more likely to be employed in Wave 5 (up to eight years post-high school; B = 0.33, p = 0.04). Discussion: Results suggest that independently traveling to places outside the home, using public transportation, and arranging airplane or train trips predict post-school employment for youths with visual impairments. Positive self-beliefs about work for pay, financial self-support, and independent living were also associated with employment. Implications for practitioners: Professionals can support students in gaining these vital skills by providing community experiences, positive role models, and verbal encouragement. Research-based predictors of employment should be considered when planning transition services for adolescents with visual impairments.