This study focuses on experience of Job Coach in Occupational Rehabilitation Support Projects that is offered by the field at the Field-Centric Occupational Rehabilitation Centers. The purpose of the study is to present better support to field training customized for people with severe disabilities. For this purpose, the researchers employed qualitative case methodology, conducted an in-depth interview with 6 Job Coaches to collect data, and analyzed collected data through constant comparison and analysis. The findings were as follows: training assistants began their work with no previous experiences with the vocational training of people with severe disabilities, but they witnessed changes to trainees and felt rewarded through their experiences of supporting the trainees. During the training sessions implemented at the establishment where trainees would be employed, the Job Coach worked together with them by their side and supported them through repetitions and praises. The Job Coach put greater importance on sociality than vocational training and spent four hours from the start to the end of their daily work on inducing the trainees to engage in conversations or having educational talks on detailed topics such as manners, hygiene, attitude, and sexuality. They had a relationship of trust with trainees, a relation of cooperation with the participant workplaces, and a relation of mutual need with trainees’ caregivers, but their employment relationship with the employed agency was ambiguous, which raises a need for institutional and administrative supplementation. Finally, Job Coach had difficulties with excessive workload, poor benefits, unclear work boundaries, difficult recruitment of trainees, and unrealistic performance goals. These difficulties can be resolved by supporting the greater professionalism of training assistants, improving their benefits, and rearranging their identity and job assignment.