The role of the community college chief academic officer (CAO) is undergoing a significant change in the twenty-first century due to an evolving higher education environment. Community colleges are facing continuous enrollment declines, have fewer financial resources to draw upon, and are under an increasing amount of external pressure, leaving senior leaders with a new set of challenges. Simultaneously, women are moving into the role of the community college CAO at a faster pace than their counterparts at four-year institutions. The purpose of this interpretive phenomenological analysis was to examine the leadership experiences of women chief academic officers at community colleges within the State University of New York (SUNY) system. SUNY's 30 community colleges make up nearly half of its 64 campuses. Eight women, currently serving as a community college CAO, participated in this study through a semi-structured interview and were asked to describe their leadership experiences as a CAO. The Synergistic Leadership Theory served as the theoretical framework through which to view the participants' responses. This study found that the role of the community college CAO, with respect to the women who serve in it, is evolving and increasing in its responsibilities, identified essential skills needed by today's CAOs, indicated that the participant's viewed their gender as a challenge, discovered there is no CAO role-specific training, and noted the majority of these women are not pursuing a college presidency. Recommendations center on the need for: additional preparation for the role of CAO, an increase in national awareness about the current literature and trends on this population of leaders, further development of opportunities to support a transition to a college presidency, and updated curriculum within doctoral coursework and programs, particularly those aligned with community college leadership.