Autism Spectrum Disorder (ASD) is often characterized by a challenge in social skills, including the ability to interview successfully for jobs, a key hurdle in transitioning towards independent living. Employment interviews require mastery of a variety of skills that can be challenging for transition age youth with ASD. Building on previous work that suggests video modeling as a viable approach to teaching vocational skills, I evaluate the efficacy of peer and self-modeling for employment interviews across a variety of industries. I also study the impact of persuasive design on motivation and technology use. In this thesis, I present results from an iterative study of the feasibility and use of VidCoach, a prototype video modeling application. Results of the efficacy study indicate that use of video modeling can produce some improvement in interview performance. The use study produced deep understanding of use as needed in the specific context of mobile technologies for transition age youth with ASD. Persuasive design showed promise in motivating and positively impacting use of the VidCoach system for job interview preparation. Both studies exhibited the potential of a video modeling system to promote behavior change, but additional work should be undertaken to determine the actual impact and present evidence to that effect.