Current literature that suggests that work redesign contributes positively to teacher job satisfaction has a largely theoretical, as opposed to empirical, basis. By using data from one state-sponsored career ladder program, this study examines the interrelationships between work redesign, work rewards, values, and teacher job satisfaction. Participation in work redesign is found to be associated with job satisfaction among more experienced teachers but not among their less experienced counterparts. The interpretation of results explores this dichotomy of findings related to teachers with differing experience levels.