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Timothy Caskey began their work experience in 1987 as a Programmer at Royal & SunAlliance. In 1994, they joined Penn National Insurance and held various roles, including Sr Programmer, Sr Applications Development Specialist, Mgr Enterprise Architecture, and Director of Enterprise Architecture. As of October 2021, they are currently serving as the VP of Information Technology Operations at Penn National Insurance.

Timothy Caskey obtained a Bachelor of Science (BS) degree in Information Systems from Shippensburg University of Pennsylvania. Timothy attended from 1982 to 1986. In addition to their degree, they have also acquired a certification in Decision-Making Strategies from LinkedIn in August 2023.