Introduction: Early work experiences are a key predictor of future employment for transition-age youths with visual impairments. We investigated how specific characteristics of early work experiences influence future employment and whether the receipt of Supplemental Security Income (SSI) benefits is associated with early work experiences among this population. Method: Secondary data analyses were conducted using four waves of data from the second National Longitudinal Transition Study, which included a nationally representative sample of high school students with visual impairments who were receiving special education services. Results: Future employment outcomes were positively associated with the characteristics of early work experiences, including finding a job independently, holding multiple jobs, and holding jobs for longer periods of time. Participating in school-sponsored work was not associated with future employment. Youths who received SSI benefits were significantly less likely to engage in productive activities, including employment, in Wave 3 than were those who did not receive benefits; however, this was not the case for youths who received SSI benefits in Wave 2. Discussion: Not all early work experiences were found to be equally predictive of future employment for youths with visual impairments. The results indicate that it may not be sufficient for youths simply to be employed during high school without consideration of the types of work, how the jobs were obtained, or how long the jobs lasted. These characteristics of early work experiences are important to future employment and should be considered when helping youths prepare for the transition from school to work. Implications for Practitioners: Professionals and parents should emphasize the benefits of early employment to youths with visual impairments. Youths should be encouraged to obtain multiple work experiences during high school while keeping in mind that longer job tenure is also positively associated with future employment. Professionals should particularly encourage youths who receive SSI benefits to obtain early work experiences and should inform them and their families about incentives that allow them to retain benefits while working.