Job satisfaction is important for employee well-being and retention, which are both crucial for high-strained occupations such as teachers and school principals. We investigated the structure and relationship of teachers' job satisfaction (N = 142,280) and principals' job satisfaction (N = 8,869). Results of structural equation modeling using multilevel bifactor models provide strong evidence for the validity of a model including both specific (satisfaction with the profession vs. the working environment) and general job satisfaction factors. This differential conception of job satisfaction was further tested by including the student variables disciplinary climate and student achievement from linked TALIS 2013-PISA 2012 data. Only teacher job satisfaction factors (general and working environment) were related to the disciplinary climate perceived by students, whereas the working environment job satisfaction factor was related to student achievement for both teachers and principals. Controlling for socioeconomic status reduced these estimates, but did not change the pattern of results.