As institutions face uncertainty in enrollment projections due to changing demographics, the impact of the COVID-19 global pandemic, and stagnant high school graduation rates, focusing on improving student retention is important. Enrollment management models provide opportunities to assess the effectiveness of enrollment strategies and make improvements to increase the number of students an institution enrolls and improve the support and outcomes of those students through degree completion. This dissertation provided much needed research on the decision-making and execution processes around student retention initiatives. Using qualitative methodology through case studies at two institutions, institutional perspectives were investigated on (a) the processes by which institutions decided to execute retention-based initiatives and organizational structures, (b) the key players, and (c) how they helped coordinate the execution of student retention initiatives to improve student retention and graduation rates. Given the focus on impacting change, organizational change management theory, specifically Kotter's (1996) eight-stage process for creating major change, guided this study. Findings suggested four main themes. First, the sense of urgency an institution is facing plays an important role in creating change necessary for improvement. The greater the sense of urgency, the greater the awareness, providing an opportunity to impact change. Second, in the absence of urgency, setting institutional goals can also impact change. Building a sense of urgency from a real crisis, or artificially creating one through a lofty but achievable goal, can help motivate institutions to move forward and impact change. Third, perhaps more important than sense of urgency itself is having the right leadership via a champion to impact change. However, to sustain change, champions must develop additional leadership to help them execute new initiatives. Finally, turnover (or lack thereof) can play an important role in a change process, both as an opportunity and a threat. Each of these themes were important to the institutions observed in this study, but in each case, the themes manifested differently. [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.]