The significance of this study was to give an active voice to the experiences of women superintendents. By giving voice to the lived experiences of women superintendents, the study sought to further understand the phenomenon of women dominating the teaching profession and other entry-level positions in education yet having a noticeably limited presence in the superintendency. More specifically, studying the barriers and supports women superintendents encounter could lead to significant opportunities to narrow the gender gap of women in the superintendency. Bringing awareness to the barriers and supports women superintendents experience could also foster more equitable workplaces. This qualitative, exploratory study aimed to identify barriers and supports faced by women school district superintendents as they ascended into the role and while they serve in the role. In this basic qualitative study, the researcher’s data sources involved semi-structured, one-on-one interviews with women superintendents. Results of the study indicate that participants felt that advancement factors were multifaceted and systematic, and employment pathways impacted options. In addition, personal obstacles acted as a barrier to reaching the superintendency. Also, gender discrimination was present while ascending to the superintendency and while serving in the role. Results also concluded that women superintendents credited their ongoing success to mentors and professional development. Implications included the need for awareness of leadership development opportunities for women in education, elimination of the glass ceiling, and additional research from women who aspire to be superintendents.