The purpose of this research was to understand the contexts that support the barriers to women’s advancement and to identify the conditions under which women leaders overcome the barriers to attain top corporate leadership positions. I have identified and discussed three distinct approaches for understanding how we can increase women’s representation and influence in the executive and director ranks within top U.S. corporations. The first approach investigates the complexities of leveraging the social and cultural capital attained through post-secondary education in order gain entry into the corporate elite. The second approach examines gendered stereotypes of risk-taking versus the organizational risk-taking realities that are inherent in women corporate leaders’ climb to the top. The final approach considers the impact of external pressures in increasing the prevalence, power and influence of women corporate directors. Findings reveal some of the complexity in both the antecedents and consequences of gender diversity within top leadership of large U.S. firms. Taken together, the results convey the organizational and societal contexts that lead to more diverse corporate leadership.