This study explores the relationship between CEO gender transition and strategic reorientation within organizations, emphasizing the moderating role of environmental context. Drawing on upper echelons theory and institutional theory, the research investigates how a shift in CEO gender—either through succession or transition—affects strategic decisions such as innovation focus, diversification, and stakeholder engagement. Using a multi-industry dataset of firms that experienced CEO gender transitions over the past decade, the study finds that strategic reorientation is significantly influenced not only by the gender identity of the new CEO but also by contextual factors such as market dynamism, regulatory pressures, and cultural expectations. Results indicate that female CEOs are more likely to pursue socially responsible strategies and adaptive innovation in complex environments. These findings offer important insights into leadership dynamics, gender diversity in top management, and the adaptive capabilities of organizations in varied institutional settings.