Thousands of students graduate from academic sport management programs annually with hopes of breaking into the sport industry. However, securing full-time employment becomes a challenge for many sport management graduates. To examine the transitional period in which graduates seek employment, the current study interviewed people who had recently earned a sport management degree (n = 16) to explore their experiences during the job search process. Given the racial demographics of participants (eight Black, eight White), the findings provide particular insight regarding racial differences and barriers Black graduates face. Findings illuminate the importance of sport management graduates strategically networking, developing targeted experiences, and considering a realistic entry point when transitioning from the classroom to the industry.