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Leon Winkler has extensive work experience in various companies and positions. Leon began their career as the Director of Customer Service Operations at Office Depot, Business Services Division, where they managed the regional customer service operations center. Leon then moved on to Safeco, Inc. as the Manager of the Claims Service Center, where they oversaw the servicing of automobile policyholders, claimants, and insurance agents. At Access Insurance Company, Inc., Leon served as the Senior Director of Customer Service, leading the company's customer service efforts as it experienced significant growth. Leon then joined Ricoh USA, Inc. as the Director of Customer Administration, responsible for managing and accessing information to support the changing workforce. Most recently, Leon has been working as the Director of Contact Center Operations (Customer Retention) at Aaron's, Inc., a specialty retailer serving consumers through sales and lease ownership.

Leon Winkler attended Prince George's Community College in 1991 for a Management Institute program in Business Management. Leon has also obtained several certifications, including "Be the Manager People Won't Leave" in September 2023, "A Manager's Guide to Inclusive Teams" in August 2022, and "Managing Virtual Teams" in July 2021, all from LinkedIn.