The role of the K-12 school superintendency remains predominantly white and male. However, there has been a slight increase in racial and gender diversity in the past several decades, as documented in the American Superintendent 2020 Decennial Study. The American Association of School Administrators' (AASA) 2020 decennial study revealed the number of female superintendents grew from 13.1% in 2000 to 24.1% in 2010, and most recently has increased slightly to 26.7% as of 2020. Still, very little scholarship exists on centering the experiences of women of color who have risen to the school superintendency. This study aims to address this research gap through the following questions: (1) What are the career paths women of color take on their journeys to the superintendency? (2) How does a woman's specific racial ethnic background get reflected in challenges and opportunities for the superintendency? (3) What skills, strategies, and support have contributed to the success of women of color in the superintendency? In this qualitative comparative case study, I conducted semi-structured interviews with six women of color superintendents and two search firm consultants from the state of California. Findings reveal the following: 1) that career paths for these women of color superintendents include both formal and informal preparation to meet the political demands of the superintendency, and their ascension to the superintendency was obtained primarily through the instructional leadership roles, although non-instructional experiences were desirable; 2) that the search and selection process, the role of search consultants, and the school board composition and politics implicate challenges and opportunities related to a woman's racial and ethnic background; and 3) the resilience factors and support systems that contribute to the success of women of color in the superintendency. Findings offer empirical support for women of color aspiring to serve in the superintendency and have several implications for leadership, school board, and system practices and policies toward improving diversity at the highest appointed leadership position in K-12 educational systems. [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.]