This qualitative research study on the lived experience of women of color heads of independent schools explores women’s professional journeys and their approach to leadership. There are over 1,400 member schools represented by the National Association of Independent Schools (NAIS). Non-Caucasian women make up approximately 1.35 percent of all heads of school (NAIS, 2010). A gap exists in current literature as it pertains to women, and in particular women of color heads of NAIS schools. In this study, the intersections of race, class, and gender are examined as part of the conceptual framework. This study employs a phenomenological approach to explore how women of color experience leadership and exercise their leadership roles in what is often seen as the rarified world of elite private schools. The primary means of data collection is semi-structured in-depth interviews based on grounded theory analysis. This study intends to contribute to current literature and provide an emerging substantive theoretical framework of culturally relevant leadership specific to the women of color heads of independent schools that participated in this study.