Orlando Winfrey is an Assistant Vice President and Branch Manager at Wintrust Bank in Chicago with over a decade of experience in retail banking, small business lending, and community development. After earning his B.A. in Business & Corporate Communications from Northern Illinois University, he built his career at Enterprise Rent‑A‑Car, UpSurge FiSo, Countryside Bank, and Wintrust Bank, honing skills in operations, sales, marketing, and fundraising. Today he leads Wintrust’s branch strategy, relationship banking, and financial education initiatives. Orlando is also a co‑host of The Franchise Power Hour on My Radio Chicago, using the platform to spotlight entrepreneurs and promote Chicago’s local arts and small‑business scene. A devoted father and husband, he mentors young professionals, supports community events like Kheemerfest, and advocates for financial literacy and entrepreneurship.