It is predicted that hundreds of chief enrollment management officer (CEMO) positions may become available due to high turnover within the next few years, creating an opportunity for a new generation of leaders. In this causal comparative quantitative study, data was collected from 211 current CEMOs to understand the challenges and highlights of the role and provide recommendations for reshaping the role. Tenets from transformative leadership theory, feminist theories, and labor economics combined to form the theoretical underpinnings for this study. Structural equation modeling was used to examine the relationship between demographic and work-life factors on job satisfaction, morale, and intention to stay. The findings suggest that career support, recognition for competence, and favorable working conditions were significantly correlated with higher morale and intention to stay in their current position. Findings from this research can help institutions make the CEMO role more attractive to the next generation of diverse transformative leaders who will be responsible for solving complex problems in the changing, highly competitive landscape of higher education.