Many people believe that U.S. higher education is at a crossroads as tuition costs soar, diversity of the student body grows, and the number of traditionally aged students enrolling in college continues to decline due to lower birth rates in the early 2000s. Today's societal, political, and cultural pressures are unique and thus put added pressure on educational institutions and the individuals who lead them. While corporations have long implemented succession planning to ensure business continuity, as an industry, higher education has been slow to embrace this strategy. In some instances, succession planning has occurred at the presidential level but not at the middle manager level. This study provides insight into succession planning, engagement attributes (i.e., job embeddedness), and work engagement characteristics of enrollment management middle managers that can be leveraged in succession planning. As shared in the literature, a lack of succession planning in U.S. higher education--where voluntary turnover is anticipated and planned for--is impacting operations broadly and enrollment management specifically. Enrollment management areas, such as financial aid, face increasing knowledge gaps as Baby Boomers and other generations retire, change careers, or join the gig economy. Lastly, younger generations in today's workforce do not feel obligated to stay with one job for lengthy tenures, which could impact a unit's bench strength. Following the COVID-19 pandemic, there is a need for ongoing research in this area as new generations enter the workforce and as work preferences and expectations change. [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.]