The purpose of this qualitative case study was to explore the ways in which cultural and gendered expectations affect the experiences of Latinas in their attainment of a superintendency in California public school districts. Six Latinas, currently serving as superintendents in rural, suburban and urban areas of Northern California, the Central Valley, Southern California, and the coastal region participated in this study. A case study approach was employed to collect, analyze, and interpret the data. This design provided for an in-depth exploration of the barriers and contributors to the professional success of the participants. LatCrit and Feminist theoretical frameworks, in connection with the tenets of marianismo, were used to draw themes associated with the unique experiences of Latinas as they ascend into the superintendency. The six themes that emerged from this research were: (a) stereotyped roles in family structures; (b) defiance of marianismo; (c) sexism along the leadership pathway; (d) lack of role models; (e) mentorship and sponsoring; and (f) nurturing leadership. This study contributes to the knowledge base by recognizing how the unique cultural and gendered experience of a Latina affects her trajectory toward the superintendency in California. [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/en-US/products/dissertations/individuals.shtml.]