Despite the multiple benefits for Supplemental Instruction (SI) leaders who facilitate study sessions for peers enrolled in high failure rate courses, those employed in large programs frequently become frustrated with their leadership development and position. Additionally, a significant percentage of SI leaders are first-generation, whose feelings of diminished satisfaction with the program maybe compounded by additional socioeconomic or familial factors. The purpose of this action research study was to create a more dynamic organizational environment for first-generation SI leaders through the creation of transformational experiences centered around elements of thriving, strengths, and self-authorship. This study addressed the following question: how can I implement an equity focused student employment experience where student SI leaders thrive as a result of their developed sense of agency and ownership in the SI program? In this study, 14 SI leader study participants engaged in training, leadership development sessions, and written reflections. It is significant to note this study's implementation occurred within the historical context of 2020, which influenced the study and its findings on student success. This study revealed two major findings: (a) SI leaders thrived as a result of their developed self-authorship, agency, and program ownership, and (b) SI leaders thrived within the historical context of 2020. Implications for policy and practice include the creation of a cohort, mentoring, and strengths-based model for SI programs. [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.]