Leon Williamson, Market President at iHeartMedia Indianapolis

Our guest on this 45th episode is Leon Williamson, Indianapolis market president for iHeartMedia. Leon shared his career journey from his Jamaican roots to leading one of the largest media organizations in the world. Leon reflected on the cultural shifts he experienced moving from Miami to the Midwest, and the importance of building local community and cultural connection both personally and professionally. Leon also discussed how his sales background and authentic leadership style have shaped his approach to managing diverse teams and fostering organizational success. Finally, he offered thoughtful insights on the evolving discourse around diversity, equity, and inclusion, and how individuals—particularly young or underrepresented professionals—can develop the confidence and clarity needed to lead with purpose and conviction.