Despite holding a majority of lower and middle management positions in public two-year institutions, women still hold only one-third of current community college presidencies. This study explored the gendered phenomenon of navigating the career pipeline in higher education to reach the office of community college president. The purpose of the study was to examine the educational backgrounds and career paths of recently-appointed female community college presidents, as well as the barriers and sources of support they encountered while navigating the career pipeline. A phenomenological approach was utilized for this qualitative study. Data was primarily collected using semi-structured interviews. Additional sources for data collection include reflection logs, memos, and document analysis. A modified van Kaam method of data analysis was used to code participant data and identify recurring thematic elements. These recurring thematic elements provided the foundation for individual descriptions of the phenomenon, which were later synthesized to create a composite description. Results suggest that study participants encountered three types of barriers while navigating the career pipeline in higher education: institutional, birdcage, and internal. The term “birdcage barriers” was coined here to describe scenarios in which aspiring female leaders could identify opportunities for professional growth or advancement, but were unable to access these opportunities because of situational boundaries. Findings also suggest study participants benefited from three sources of support: institutional, personal, and individual traits/strategies. Additional findings include: participants were reluctant to label gender a barrier; most of the institutional bias encountered by participants was second-generation; and, as aspiring leaders in higher education, participants required intrusive recruitment.