The problem addressed in this study was the underrepresentation of women in leadership positions in higher education institutions. The purpose of this qualitative descriptive case study was to understand the perspectives and experiences of underrepresented women in leadership positions in one community college system. The qualitative case-study design allowed for each participant to describe their journey and help build a roadmap for future female leaders. Through this study, I shared the experiences of female leaders in a large community college system, their stories of reaching their current positions, and explored barriers or challenges they may have faced. The research questions were developed and reviewed within the lens of social role theory. Purposive sampling limited the selection to those leaders who were part of a relevant sample and elicited the responses specific to the target population. The sample size chosen was 12 participants, all of whom were female, and were senior leaders with the title of president, vice chancellor, vice president, provost, or dean. I concluded at the completion of this study that there is a consistency of experience and obstacles for female leaders in the chosen community college system. Future researchers could add to the literature and confirm results by studying other community college systems or by interviewing male colleagues to validate the female leaders' perspectives regarding the difference in male and female experiences. Although there were diverse paths to the position described, most participants cited obstacles in the form of social expectations that they have encountered and overcome. Additionally, all participants indicated the necessity to have a good support system to succeed. Finally, the participants were all willing to provide this same support for future female leaders. Higher education leaders could use the information gathered in the study to inform their preparations for promotion and to avoid obstacles encountered by the participants.  [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]