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Stephen Weiss has a diverse work experience in the IT and healthcare industries. Stephen served as the Managing Director and CIO at DirectTrust, where they supported secure health information exchange. At AllegraMD, Inc., they held the positions of CIO and COO, providing consulting services and managing technical operations. Stephen also worked as a Senior Vice President at Vandam Consulting Services and as the CIO/COO at MDwerks Inc., a financial services company. Stephen was the CIO/COO at Enterprise Technology Corporation, where they managed operations, technology, and client projects. Additionally, Stephen co-founded Imagine Networks and served as the Chief Technology Officer, overseeing the development of prepaid debit card technology.

Stephen Weiss holds a Bachelor's degree in Chemistry from Buffalo State University.