In keeping with the special issue centered on Gender and Race in the Workplace, this article explores the role that the intersection of race and gender played in the attainment of the superintendency for four Black women superintendents. Despite their increasing presence in educational leadership, Black women continue to experience marginalization such as being overworked, undervalued, and overlooked in the workplace. By examining the barriers these women faced as well as the ways in which they overcame them, much can be weaned from their wisdom and experiences for future aspirants as well as current superintendents. This article highlights the journeys of four Black women superintendents which underscores their intersectionality experiences drawing upon their resilience to achieve success. Their stories, especially in light of the increasingly violent and racially charged settings in which they find themselves, are necessary and deserve a voice. The findings have implications for research and practice.