Harold Shepard II is a seasoned professional with extensive experience in leadership, sales, and marketing across various industries. Currently serving as Agency Lead at Combined, a Chubb Company since September 2024, Harold is responsible for recruitment and training while driving business growth. As Co-Founder and COO of GEST Carts Chicago, Harold leverages innovative OOH marketing strategies to engage Chicago's market. Previous roles include Vice President and Employee Benefits Consultant at USI Insurance Services, where Harold focused on analytic-driven solutions for B2B clients, and Sales Associate at Aflac, achieving top sales performance. Additional experience includes sales and marketing roles at Chicago Scene DMC and Altered Stage, showcasing a strong ability to execute campaigns and manage projects effectively. Harold holds a Bachelor’s Degree in Entrepreneurship from the University of Illinois Chicago.
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