Higher education institutions continue to make significant strides in increasing the number of women in leadership positions, however, there continues to be an underrepresentation of women in leadership positions at higher education institutions in the Western United States. To explore the underrepresentation of women in leadership positions, the study focused on women's opportunities and barriers to advancing into leadership positions. The barriers identified focused on societal perceptions of women in leadership roles in higher education and organizational cultures. This study is significant to women attempting to attain a leadership position and for those already in leadership who are still affected by organizational biases and the lack of opportunities presented. The combined conceptual framework for the study highlighted how societal perceptions and organizational cultures play a critical role in the existence of inequitable opportunities, gender biases, preconceived organizational images of what a leader should look like, and gender disparities. These influences contributed to biases, some unconscious, in the decision-making process when considering a woman for a leadership position. The qualitative research using a single case study design allowed for the administration of open-ended surveys and interviews with 23 women currently serving in leadership positions at the institutions. The data collected will be used as a transformative learning experience, supporting the advocacy of women in leadership roles, and presenting the various organizational biases as a challenge that needs to be addressed. The research revealed reoccurring themes that emerged from the data and included discussions on gender bias, models of leadership, opportunity, and development, and misconceptions of women as leaders. The findings revealed implications for practice and policy within the higher education system. The implications for practice should be concentrated on developing an institutional climate that embraces transformative leadership. Additionally, develop a systemwide women's leadership initiative that presents a safe platform for women to develop leadership skills, and network with other aspiring women interested in becoming a leader within higher education. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]