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Randy Thompson has a diverse work experience in the voluntary benefits enrollment field. Randy began their career at Impact Enrollment Solutions / iBenefit Communication as an Account Manager, where they oversaw case management services, supported clients as their main point of contact, managed enrollment strategy and logistics, and recruited and trained the enrollment team. Randy then joined Stratovize, LLC as a Senior Account Manager, responsible for evaluating client needs, engaging carriers, managing the RFP process, determining benefits offerings, and overseeing the enrollment process. Randy later became the Director of Enrollment Strategy at Stratovize, where they managed the transition and implementation of benefit programs, achieved financial goals, and served as a key liaison with clients and carriers. Most recently, Randy joined The Warner Companies as the Director of Voluntary Benefits Enrollment Strategy.

Randy Thompson attended Towson State University from 1976 to 1978, where they pursued a degree in Business Administration with a concentration in Marketing. Later, they also attended Harford Community College to further their studies in Business Administration, although the specific years are unknown.