The role of a college president continues to present new and evolving challenges. Cuts to federal and state funding, declining enrollment, rapid changes in technology, and the uncertainty caused by the COVID-19 pandemic, paired with ongoing retirements, have left higher education leaders with a new set of challenges. While women are beginning to move into senior leadership positions quicker than in past decades, they continue to lag behind men in their advancement to the presidency. The purpose of this Interpretative Phenomenological study was to examine the lived experiences of community college chief executive officers in the Mid-Atlantic region of the United States who served or still serve as the first woman president of a two-year institution. Six women presidents participated in this study and shared lived experiences of their pathway to the college presidency, as well as the successes and challenges faced in becoming the first woman leader. Synergistic Leadership Theory served as the theoretical framework through which participant stories were viewed. Five themes emerged from this study: 1) the decision to pursue presidency; 2) the impact of gender; 3) external forces; 4) the importance of networks, mentors, and a personal support system; and 5) advice for aspiring women presidents. Recommendations focus on the need for: development of intentional leadership pipelines, diversification and training of the board of trustees, accessible leadership development for aspiring presidents, and the evaluation of Synergistic Leadership Theory as an effective framework for studying leadership in 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://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]