In this study, we clarified the effect of training by enterprise size for the training service (TOSA Marugoto Business Academy Project [Tosa MBA]) provided by Kochi Prefecture in Japan by applying structural equation modeling to online survey data. In large enterprises, expert knowledge that can be used at work had a positive effect on job satisfaction rather than career status such as annual income and job title. This may have been the case as while promotion involves higher wages and greater privileges, in large enterprises, the extent of responsibility and working hours increase even more. Conversely, in small and medium-sized enterprises (SMEs), career status has a more positive effect on job satisfaction than does expert knowledge. For SMEs with a simple organizational structure, job position has a greater influence on work attitudes. The results present meaningful suggestions to enhance the design of local government training services.