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Wendell Crain has extensive work experience in the field of information systems and security. Wendell started their career at Communicolor, Division of Standard Register, Inc. as a Production Programmer in 1990 and worked there until 1997. Wendell then joined The Relizon Company (formerly Reynolds & Reynolds) as a Manager for Variable Image Systems, where they were responsible for project management and the startup of the department. In 2003, they joined MedBen as a Programmer and gradually progressed to positions such as Senior Programmer Analyst, Technical Specialist, and Manager of Technical Services and Web Development. Wendell is currently serving as Vice President of Information Systems and Chief Security Officer at MedBen.

Wendell Crain obtained their Bachelor of Arts (B.A.) degree in Business Administration from Mount Vernon Nazarene University from 1997 to 1998. Prior to that, they earned an Associate's degree in Data Processing from Muskingum Area Technical College from 1982 to 1983. In addition to their formal education, Wendell has also obtained certifications such as the Community Leadership Program from Licking County Chamber of Commerce in May 2018, and the Cisco Certified Entry Level Technician (CCENT) in June 2014.