The journey of Black women into senior leadership roles within higher education institutions is characterized by a complex interplay of personal and professional realms shaped by the intersecting forces of racism and sexism. This dissertation examined the lived experiences of these trailblazing leaders, revealing the systemic barriers they encounter, the resilience they embody, and the strategies they employ to navigate and transform the academic landscape. Through a rigorous qualitative approach, this study gives voice to the narratives of Black women in positions such as university deans, vice-presidents, and provosts. It explores the multifaceted challenges they face, including the questioning of their legitimacy, marginalization, and the persistent confrontation with racist and sexist stereotypes. The research underscores the emotional labor and toll these experiences can have on their well-being and their decision to remain in or leave their leadership roles. Central to this study is examining workplace factors that contribute to or detract from Black women leaders' sense of belonging, job satisfaction, and intent to remain. It highlights the critical importance of supportive networks, mentorship, and institutional policies promoting diversity, equity, and inclusion. The study explored these leaders' strategies to navigate adversities, build support systems, and advocate for change within their institutions. Furthermore, this dissertation sheds light on the institutional factors and policies that can foster the retention and advancement of Black women in higher education leadership. It emphasizes the need for comprehensive mentorship programs, targeted professional development initiatives, and inclusive spaces celebrating diversity. The research also underscores the significance of work-life balance policies that acknowledge the holistic needs of Black women leaders. Through this in-depth exploration, the study contributes to a deeper understanding of the systemic issues influencing the career trajectories of Black women in academia. It calls for a concerted effort to dismantle barriers and create a more equitable and inclusive higher education landscape where Black women's unique perspectives and contributions in leadership roles are valued and amplified. Overall, this study is an essential resource for advancing knowledge and understanding in the field, and its implications can potentially influence positive change in academia. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]