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Educational facilities management organizations are white, masculine, and patriarchal, with an ingrained culture that breeds racism, sexism, and classism, creating oppressive work environments that discourage Black women from leadership. This paper employs a multi-case study as methodology and a Black feminist framework to investigate how four Black women who hold leadership positions in these organizations negotiate and navigate these oppressive work environments. Although analysis is ongoing, preliminary findings show that the participants use their knowledge, relationship networks, unique abilities, and agency to confront oppression as they advance to and sustain their leadership positions. These promising results may help us understand ways we can dismantle oppressive culture and, in turn, create pathways to increase the representation of Black women leaders.