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This chapter provides an analysis of the plight of African American women leaders as they journey to the superintendency. African American women remain largely underrepresented in the superintendency. Although the number of women superintendents has increased over the years, the superintendency remains a male-dominated field and African American women remain in the minority. Consequently, African American female superintendents must overcome many obstacles such as racial and gender stereotypes, caustic work environments, and restricted access to opportunities. Critical to dismantling the underrepresentation of women superintendents is the role of mentorship and hiring practices on the recruitment and retention of Black women superintendents. Mentorship is an essential strategy in weathering these barriers. African American women also deserve a voice in the hiring practices of school districts. Further, when marginalized groups, such as Black women, are placed at the center of hiring discourses, hidden paradigms and vestiges of discrimination will be unearthed to unify efforts to provide increased opportunity and positive workplace environments. These efforts have implications for research and practice in the area of mentorship and hiring to amplify the voices of African American women superintendents and presence in the superintendency.