This 2-year pilot study aimed to investigate the effects of a job coaching application (i.e., Job Coaching on Demand) on the knowledge and competencies of teachers and job coaches that work with young adults with developmental disabilities. Due to the global pandemic, this research was conducted virtually over a 2-year period. During the first year, a one-group formative pretest/posttest design with key informants was used to pilot the app with three teachers and five job coaches. The anecdotal findings from this pilot year were then used to further develop the application. The intent of the application was to provide professional development support to teachers and job coaches across the categories of (a) exploring careers, (b) ready for work, (c) part of the team, and (d) advocacy. In Year 2, a total of 31 teachers and job coaches were recruited, and a pretest/posttest was conducted to compare the differences in gained competencies between the two groups. The results show that those in the treatment group showed a larger increase in gains compared to the control group. The overall results of the 2 years of data, the current application development, and practical implications of the technology are further discussed.