This qualitative study explored the perceptions, challenges, and lived experiences of women, in the Commonwealth of Kentucky, holding executive level leadership positions to inform tailored support strategies. As female educators aspire to higher levels of leadership in schools and districts, limited avenues of structured informal and formal support exist. A review of literature reveals an understanding of how female educators have been historically positioned in education which provides a foundation for present day challenges. Research is lacking on utilizing these lived experiences and challenges as a source to provide informed support. In order to take educated steps to a more equal and equitable playing field for women, this study provides insights on support practices women experienced progressing through executive level leadership positions. The multiple case study research design was selected to illuminate the phenomenon through viewpoints by assembling data from individual cases. Data was collected from interviews of ten women in executive level leadership positions at the school and district level. Interview transcripts were analyzed individually and holistically to identify common themes of participant lived experiences and challenges. This study finds that aspiring and current women executive level leaders need a combination of formal and informal support approaches, intentionally structured, to combat the negative impact challenges women experience. Implications for the field of education point to a stronger collaboration between schools and districts, higher education institutions, and professional organizations for recruitment and creating sustainable support systems for aspiring women leaders earlier in their career. [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.]