As presented in the qualitative research study, women represent only 27% of all 14,000 superintendents nationally (American Association of School Administrators [AASA], 2020) and 30% in New York State (NYS Council of School Superintendents [NYSCOSS], Snapshot IX, 2015). This study was based on a qualitative description design, in which the methodology was comprised of in-depth semi-structured interviews used as the chief source of data. Specific to gendered organizations and the superintendency, this study focused on the Boards of Cooperative Educational Services of New York State (BOCES). As the intent of the study was to investigate women in the superintendency and why they stayed, BOCES is an organization that is representative across New York State. Therefore, 32 women superintendents from the BOCES in NYS participated with the intent to understand the "why" behind why women stay in the superintendency. In doing so, I aim to offer a new understanding regarding why women stay in the superintendency while also bringing thoughtful attention and appreciation to how these women succeed in a male-dominated field. Finally, the findings indicate that the BOCES is a gendered organization, and the women superintendents who stay within the position use personal and professional supports. To expand on Acker's theory, the supports that I examined to contribute to the research community include the value of informal mentoring and networking, internal workplace supports, use of self-care supports at work, spousal and family support, and personal support focusing on the inner self. [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.]