This qualitative study examined the role of institutional agents, defined as individuals with positional power within an institution that foster the advancement of those with limited or no power, in the entry, retention, and advancement of women of color leaders aspiring to be K-12 district leaders (i.e., superintendents, assistant superintendents, or high-level executives). As women are disproportionately underrepresented in the highest levels of K-12 leadership, this study's purpose was to better understand the ways in which the relationship between the aspiring women of color leaders and institutional agents could serve as a pathway to increase women's representation in these district level roles. I followed the qualitative tradition of interpretive research in order to better understand the sensemaking of women superintendents, assistant superintendents and/or chiefs about their relationships with institutional agents. I conducted 45-70 minute semi-structured interviews with 10 women superintendents, assistant superintendents, and/or chiefs employed by urban school districts and charter networks in the northeastern United States. Grounded in Saldana's (2016) coding methods, I identified the following themes that defined the role of institutional agents in participants' career entry, retention and advancement: role model, holistic advocate, and anti-racism/sexism guide. Additionally, I highlighted the following themes that described the impact of the participant-institutional agent relationship on the women leaders of color: ambassador for future leaders and agent of change. Implications for theory and practice are included. [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.]