Driven by dynamic competitive conditions, companies’ information technology (IT) functions adopt agile practices and build ambidextrous organizational structures, which, in turn, affect the work environment of individual IT employees. Based on the fundamental assumption of person-environment fit theory that people seek out environments which allow them to behaviorally manifest their traits, this research aims to shift the focus in organizational design choices towards an individual-level perspective. We study whether and how personality traits and work environment characteristics, measured at the individual level of ambidexterity, relate and impact person-job fit (P-J fit). The results of a survey of 279 IT workers show that personality traits (operationalized by the Five Factor Model) significantly differ across exploitative and explorative work environments. Furthermore, the data suggests that the relationship between extraversion, conscientiousness and openness to experience on P-J fit is moderated by the level of ambidexterity.