This study empirically investigates the strategic and behavioral pathways through which organizational context is associated with firm performance. Leveraging the dynamic capabilities perspective on organizational ambidexterity, we propose that ambidextrous strategic orientation (ASO) and productive organizational energy (POE) mediate the relationship between organizational context and firm performance in parallel. Additionally, we introduce CEOs’ ambimotional inspiration as a critical moderator in these pathways. Using a multisource dataset comprising 148 organizations and 13,834 employees, our findings confirm that ASO and POE mediate the relationship between organizational context and performance. Intriguingly, CEOs’ ambimotional inspiration strengthens the strategic but does not influence the behavioral pathway. These results contribute to the literature on ambidexterity by demonstrating the interactive effects of organizational context and leadership on the emergence and effectiveness of ambidexterity.