Indiana University-Purdue University Indianapolis (IUPUI) / Grounded in leadership, cultural, communication, and gender studies, this dissertation investigates the challenges African-American women executives in the philanthropic foundation sector faced as they strive to have their culture legitimated within the culture of the workplace. Through the use of case study methodology, I examined the experiences of participants by conducting oral history interviews that traced their critical path to leadership. I also incorporated my own experiences in the field to further explore the connections between race, gender, and leadership styles in philanthropic organizations. The interviews and my own auto-ethnographic research explored the possible consequences of black executive women in the foundation world not being able to share aspects of their cultural lives in workplace networks and the impact of the critical exclusion of who they really are as whole human beings on the quality of their careers. An analysis of data collected from the interviews revealed key factors critical to the success of study participants. First was the presence of familial or close adults actively engaged in philanthropic activity during the participants’ formative years. Second was a strong influence of a faith tradition. Additionally, the date revealed that participants’ involvement in outside leadership roles, often tied to their racial and gender identities, were not capitalized on by employers. This study achieved several key outcomes. First, it afforded participants an opportunity to develop the personal satisfaction of expanding the body of knowledge related to leadership development within the philanthropic foundation sector. Additionally, by sharing their stories, these individuals were able to develop or strengthen mentorship relationships. Lastly, this study has the potential of being of significant benefit to the greater philanthropic foundation sector, since it worked towards the expansion of the body of knowledge specific to the issues of gender and cultural differences within the foundation sector.