This dissertation uses a gender lens to examine the leadership and philanthropy practices in nonprofit organizations. Despite being the majority of employees in the nonprofit sector, women are underrepresented when it comes to leadership. Women face complex issues such as implicit gender bias and stained-glass ceiling when navigating the leadership maze within organizations. This dissertation explores the factors that influence the inclusion of females in leadership positions in nonprofit organizations using a mixed-method approach. By using the conceptual frameworks of the Critical Mass Theory and the Kaleidoscope Career Model, this dissertation attempts to answer three related research questions. First, using the data acquired from GuideStar, I explore how does the gender composition of staff, board, and the gender of the past CEO influences the gender of the present CEO in faith-based nonprofit organizations. The findings show that there exists a causal relationship between the gender composition of staff at senior managerial positions, the gender of the former CEO, and the gender of the current CEO. Second, by adopting a qualitative approach, this dissertation explores what gendered barriers are faced by women as leaders within faith-based nonprofit organizations and to what extent religion impacts these barriers. 23 female leaders within faith-based nonprofit organizations were interviewed using open-ended questions. This methodology helped to explore the lived experiences of the female leaders and devise their perspectives in their own words. Findings showed, in faith-based nonprofit organizations, along with religious conservativeness, internalization of gender and cultural stereotypes contribute to the challenges faced by women. And lastly, by conducting an online survey experiment using Amazon Mechanical Turk (MTurk), I explore how charitable giving is influenced by the gender similarity between the donor and the CEO. Results showed, female donors are more likely to donate to female CEOs, and less likely to donate to male CEOs. Similarly, male donors are less likely to donate to female CEOs. Results also showed, if the cause is related to women issues, female donors are more likely to donate even if the CEO is of the opposite gender. Female donors donate to a religious organization only if the CEO is a female. The findings from this dissertation are expected to contribute to the existing research by adding the impact of the gender of CEO on organizational practices such as leadership, philanthropy, and career choices made by women in faith-based and the overall nonprofit sector.