Drawing on the person–organization fit theory, this study elaborates a dual-oriented human resource (HR) system and explores when and how two HR bundles (development vs. maintenance) influence work well-being. The results of the confirmatory factor analysis with a sample of 1,946 supervisors from a Chinese high-tech firm show that the dual-oriented HR model fits the data better than a holistic HR system.In another study with a multilevel sample of 64 corporate branches and 434 employees, the findings confirm the proposed joint effect of the dual-oriented HR system and achievement motivation on well-being. Specifically, development oriented HR practices are more positively related to work well-being only when individual achievement motivation is high; by contrast, maintenance-oriented HR practices are more positively related to work well-being only when individual achievement motivation is low. Work meaning mediates these effects. These findings provide guidance on the effective design of HR practices.