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Scholarly literature focusing on organizational environments and organizational fit highlights the importance of a Multi-Fit perspective, which includes person–environment fit, person–culture fit, and person–vocation fit. However, relatively few scholars in sport management have focused on the organizational environment that includes sport management faculty and doctoral students. Therefore, the purpose of this study was to examine sport management doctoral programs to evaluate how sport management faculty and sport management doctoral students assessed the academic environment. Findings from 15 sport management faculty and 13 doctoral students resulted in three distinct overarching themes: (a) initial evaluations from person–environment fit, (b) fitting in with person–culture fit, and (c) the gap in person–culture fit. Moreover, subthemes emerging from faculty were (a) coachable, (b) well-roundedness, (c) experience, (d) research interests, and (e) statistical knowledge. Subthemes emerging from sport management doctoral students were (a) funding, (b) initial contact, (c) geography, (d) foundation, and (e) cohort mentality. The findings of this study have significant importance to the sport management academy as scholars have suggested approximately 50% of doctoral students fail to receive their degree, and cohort entrance and exit attrition may be as high as 85%. Therefore, the goal of this study was to increase the extant knowledge pertaining to person–environment fit and the sport management doctoral matriculation and enrollment process between sport management faculty and sport management doctoral students.