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Gary De Jager's work experience includes several roles in different companies. From 1986 to 1990, they worked as an Office Manager and a DJ at Special Sounds. Then, from 1998 to 2000, they worked in sales at Vande Berg Scales. From 2000 to 2004, they were an Inventory Control and Human Resources Manager at A & I Products. Lastly, since 2004, they have been the Chief Human Resources Officer at Peoples Bank, where their responsibilities include overseeing all HR functions, maintaining employee records, and enforcing company policies and procedures.

Gary De Jager completed an Associate's Degree in Mass Communication/Media Studies at the Brown Institute of Technology in Minneapolis, MN from 1986 to 1988.