We investigated the effects of preference and degree of match on job performance of four 19 to 20-year-old young adults with developmental disabilities placed in community-based job conditions. We identified high-preference, high-matched and low-preference, low-matched job tasks using a video web-based assessment program. The job matching assessment provided index scores on degree of match between job requirements and participant skill levels. Each participant was subsequently placed in a randomized sequence of 30-min sessions on one high-preference, high-matched job and one low-preference, low-matched job. A job coach instructed individual participants to perform jobs, teaching tasks when necessary. We collected data on (a) productivity, (b), accuracy of tasks performed, (c) job satisfaction and (d) an independent observer's judgment. We found higher productivity, accuracy and job satisfaction across all participants on the high-preference, high-matched jobs. We discuss results in terms of assessment of preference and matching to facilitating self-determination.