Reggie Blair began his professional career working for Dell Technologies as an Inside Accounts & Sales Team Manager. In that role, he managed and developed several accounts for higher education, state and local government, and K-12 organizations. Additionally, he oversaw training efforts for newly hired sales representatives, while also coaching tenured representatives for specialty roles in corporate account development. While he enjoyed the opportunity there for many years, he felt a calling to pursue a role in higher education.

In 2008, Blair decided to make a vocational change by returning to his alma mater and starting a career in the admissions office. Blair worked in the admissions office at Lipscomb University for 13 years, ultimately culminating his career as Sr. Director of Admissions. During his time in the office of admissions, he served in a variety of capacities, including training and oversight of recruitment activities for admissions counselors, managing and directing graduate recruitment efforts for the School of Computing, operating as principal representative for local community college partnerships while increasing the recruitment and retention of prospective transfer students, admissions athletic liaison, and serving as the primary institutional contact for K-12 schools within the National Christian School Association (NCSA).

Blair joined Cumberland University as Vice President for Enrollment Services in the fall of 2021. Under his leadership, Cumberland achieved the highest overall enrollment to date of 3,072 students in the fall of 2023. He is also actively involved in several community organizations, including 100 Black Men of Middle Tennessee, Tennessee Latin American Chamber of Commerce (former board member), Information Systems Security Association (ISSA), and Alpha Phi Alpha Fraternity, Inc.

Blair holds a Bachelor of Science in Business Administration and a Master of Science in Information Security from Lipscomb University, and he is currently pursuing a Doctorate in Higher Education Leadership at Abilene Christian University in Abilene, Texas.