The California Community College system is the largest system of higher education in the nation, with 2.6 million students attending 112 colleges. Community colleges are integral to workforce development, economic recovery, and an accessible and affordable gateway for transfer to four-year universities. While community college student population is very diverse, executive leadership is not necessarily representative of these shifting demographics. Organizations and aspiring leaders may not be prepared for the mass vacancies created by impending retirements of executive leadership positions (ELP) at community colleges. This study sought, through the counterstories of female community college presidents of color, to identify challenges and opportunities for California community colleges to develop representative and sustainable executive leadership and organizational cultures inclusive and supportive of aspiring female community college presidents of color. Specifically, this study sought to illuminate various career paths of female leaders of color in higher education, as well as unique personal, professional, and organizational challenges that may hinder their ascension. Setting the context for this study are the shifting demographics of community college campuses, impending mass retirements of community college presidents in the next five years, and organizational culture and practices that may impede the ascension of female administrators of color that could present a challenge for organizations to foster sustainable and representative leadership. Within a conceptual context of Critical Race Theory, narrative counterstories illustrate the career paths and experiences of female community college presidents of color and allow the analysis of organizational culture factors to understand if and how organizational and cultural systems at California community colleges may exist that hinder the recruitment, support, and professional ascension of female community college presidents of color. [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.]