The purpose of this study was to determine whether past and present female superintendents in Colorado felt their career paths were gendered. In addition, what strategies they used to navigate their experiences were examined. A qualitative multi-case study design was used to structure this study. A social constructionism philosophy as described by Crotty (2003) guided the study. The multi-case design and epistemology support collecting multiple experiences within a phenomenon (Crotty, 2003). Participants were selected through purposeful snowball sampling. The community of female superintendents in Colorado is small and connected. This study included four retired female superintendents and five who are still currently serving in the role in Colorado. Qualitative data were drawn from three different resources. Interview transcripts, follow-up questions, and newspaper and website publications were gathered, analyzed, and coded for major themes. The data analysis suggested that female superintendents in Colorado have gendered experiences within their path towards and service within the superintendency. The findings regarding whether their experiences were gendered included themes of discrimination, gendered leadership expectations, and what motivated these nine women to pursue the superintendency. The first two were significant challenges for the women. To help navigate their way to the top, the nine women employed various strategies, including hard work, collaboration, and maintaining a strong support system. The participants felt as though they had to work harder to be noticed and had to do others\u27 dirty work at times. They relied heavily on collaborative working relationships with others, and they discussed the need to have a supportive team when reaching the top. The study has significance in helping aspiring female leaders understand the experiences and strategies of these nine female superintendents in Colorado who successfully attained the role that other women find difficult to reach. In Colorado, only about 30% of school district superintendents are female even though women make up the majority of the workforce in education (Carli & Eagly, 2016; CASE contact list; Fitzsimmons & Callan, 2016)