Reggie L. Smith
Senior Managing Director
Mr. Reggie Smith is an accomplished business leader and former professional athlete with over three decades of experience in leadership, entrepreneurship, and strategic growth. As a Sr. Managing Director at Generational Group, he leverages his extensive background to help business owners navigate the challenges and opportunities facing entrepreneurs in today’s marketplace.
Before joining Generational Group, Mr. Smith founded, scaled, and successfully sold a leading litigation support firm after 18 years—an experience that fuels his passion for helping entrepreneurs achieve successful exits. Known for his integrity, teamwork, and results-driven approach, he has built lasting relationships that consistently deliver measurable outcomes.
Combining the mindset of a competitor with the vision of a strategist, Mr. Smith provides practical, tailored strategies that align business goals with personal aspirations. His leadership is defined by discipline, collaboration, and a deep commitment to helping entrepreneurs protect and maximize the value of their life’s work.
Mr. Smith holds a Bachelor’s degree in Human Resources from the University of Kansas, where he honed his foundation in organizational strategy and people-centered leadership. He served for 6 years on the NFL Players Association National Board of Directors, as well as President for 2 terms of the Chicago Chapter.