Several acts and movements have attempted to eliminate discrimination in employment opportunities. However, despite these acts and movements, there remains a disproportionate number of males in top leadership positions in public schools. Women who hold the position of superintendent in public school districts in Oklahoma from diverse backgrounds including rural and urban districts, small and large districts, and various regional areas in Oklahoma were invited to participate in this study. This transformative qualitative case study was context bound to a group of eight women who consented to participation. The purpose of this study was to explore through the combined lenses of Schein's (1971) Organizational Career Mobility (OCM) and Kim and Brunner's (2009) filter of glass ceiling how selected women obtained and experienced their roles as public school district superintendents in Oklahoma. Data were collected through multiple sources, including demographic surveys, interviews, observations, and collection of artifacts and documents. Also, document prompts of participants' own resumes were utilized during interviews. [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.]