While scholars have addressed the challenges Black women face in various workplace environments, less is known about the psychological and social experiences of Black women leaders in the nonprofit sector. In the present qualitative study, we draw from plantation politics and intersectional leadership frameworks to explore the perspectives of Black women Executive Directors. Specifically, we examine how they navigate structural and interpersonal challenges while building and growing nonprofit organizations that serve Black girls. Furthermore, we consider the extent to which the racialized logics of plantation politics inform their well-being and social justice missions as organizational leaders. Using consensual qualitative research methods, we analyzed semi-structured interviews from 16 Black women Executive Directors of 501(c)3 nonprofits across America (33–62 years old, M = 44.6, SD = 9.7 years). We identified the following themes: (1) unsupportive and hostile nonprofit landscape, (2) subpar access to opportunities and organizational infrastructure, and (3) attrition and burnout. Our findings demonstrate a connection between structural racism—manifested as plantation politics—and the chronic underinvestment in Black women’s leadership, which ultimately undermines their well-being.