The main objective of the study was to investigate the mediating role of career management practices (CMPs) in the relationship between firm characteristics, individual characteristics, hierarchical career plateau and organizational career growth. The study took a context-dependent approach by investigating the above in mediumsized enterprises of a developing country, Sri Lanka. The data were collected from 667 employees, those who are in supervisory or above level but not an owner, partner, or a member of family of owners/partners of medium-sized enterprises. Analysis of direct effects implied that CMPs driven by both organizations and employees have positive effect on organizational career growth. Age, the level of education attainment, and the experience of hierarchical career plateau have significant effect on organizational career growth through CMPs driven by employees.