This study is a phenomenological inquiry on the achievement bridge in Latina leadership and educational advancement. The case studies used counter-storytelling to explore the triumphs and challenges of Latina leadership in superintendency. Education is in dire need of leaders who disrupt, disquiet, or unhinge oppression with the disposition of a "si se puede" or can-do attitude. This research provided contextual and scholarly frameworks that correct misperceptions of Latina leaders and showcased characteristics of success in advancement and leadership. It adopted a qualitative phenomenological approach to study Latina superintendents in the Chicago area to illuminate advancement and achievement in upper-level leadership roles. This research enriched existing educational leadership frameworks by documenting themes of genius and joy that are not often categorized around this work. It also introduced a new leadership framework, the 5i framework, which explains the stages that Latina leaders move through when navigating the professional journey. The 5i framework reveals the stages of invisibility, indebtedness, in-betweenness, impostor syndrome, and insurgence by combining narratives of achievement and challenges while capturing Latina joy, success, and celebration from Latina superintendents. The implications of this study include increased retention of diverse leadership, increased student achievement, and changes to educational practice and policy to make them more culturally responsive and inclusive. [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.]