To date, we have the most diverse workforce in history. There currently four generations of professionals within our workforce: Baby Boomers, Generation X, Millennials, and Gen Z. Millennial and Gen Z professionals have recently overtaken Generation X and Baby Boomers as the largest generational cohort in the workforce. During this generational transition within the workforce, the Student Affairs field within Higher Education has experienced extremely high turnover, impacting colleges and university’s ability to sustain student support. If this trend continues, colleges and universities will have a limited pool of qualified candidates to fill current and future leadership positions. The study will examine if generational differences impact Student Affair professional’s perception of their job satisfaction. In addition, characteristics such as gender, race/ethnicity, education level, years of experience, salary, two-year and four-year institutions, and functional area will be assessed to determine potential impact on job satisfaction for Student Affair professionals as well. This study will also determine if the Student Affair Job Satisfaction Survey (SAJSS) tool can effectively measure job satisfaction of Student Affair professionals. If proven to be effective, institutions will have an assessment tool that can be used to measure job satisfaction of their Student Affair staff to identify areas of strength and weakness. Having such a diverse workforce, colleges and universities will need to ensure their fostering a work environment that is attractive to professionals of all backgrounds to retain the best Student Affair talent.