Student affairs practitioners in higher education have been leaving the field at an alarming rate (National Association of Student Personnel Administrators, 2022). As personnel working on the front lines in efforts related to student success and retention, early-career incumbents in these positions experiencing such high rates of attrition presents an existential crisis to student affairs as a profession (Fosnacht et al., 2021). This study examined the job experience of early-career housing professionals and its relationship to retention to their positions. The study received endorsed research status by Association of College and University Housing Officers-International (ACUHO-I) in 2023. The study looked at: (a) the role of hall director as a generalist and its level of autonomy; (b) short-term tenure; (c) the impact on small, private colleges; and (d) training and development of these personnel. The researcher provided perspectives into the perceptions and factors that may influence the job experience through a single, bounded case study at one housing/residence life department. Through interviews with personnel on three levels in the organization (entry level, mid-level, and senior level), and a document analysis of a job description, training, and recruitment materials, this study examined the expectations and perceived realities of early-career housing professionals. Findings revealed the hall director position at the small, private university is complex, generalist, and mostly autonomous, with ambiguous, abundant responsibilities. The work environment is perceived as innovative and strategic, with high performance expectations to go above and beyond, and is characterized by frequent vacancies and staff turnover, hall directors challenged to balance overlapping professional and personal lives, and a perception that compensation and duties required are not aligned. The managers perceive the job skills required for the role to be technical and organizational, with graduate classroom and fieldwork preparation contributing to success in the role. Areas to explore for future research include the differences in job experience and retention between different gendered personnel, master's degree recipients in related versus unrelated fields of study, state and regional factors, and the timing of hiring cohort to start of work. [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.]