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The racial and gender demographics in education and educational leadership are disproportionate to the number of Black women superintendents. Issues of equity in opportunities, career preparation, and advancement and leadership practice are of interest and importance to practitioners, policy makers, and researchers. This qualitative inquiry of how three Black/African American women leaders’ race and gender informed their educational and professional experiences on the superintendency pathway, employed qualitative interviewing, autoethnography and ethnomethodology. Three themes: (a) Perceptions of identity(ies) (b) Non-traditional/non-linear educational and career pathways; and (c) Experiences of difference, are detailed. Additional perspectives of the superintendency within a leadership context, distinct from the past perspectives of White males, who have historically and disproportionately occupied the position, are offered.