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Chris Sheppard has a diverse work experience spanning several companies. Chris started their career as a First Year TA at the University of Waterloo in 1999. Chris then worked as a System Administrator at Quack.com before joining AOL as a Software Developer in 2001. After that, they worked at Kinitos Inc as a Software Developer from 2004 to 2011. During their time at Kinitos Inc, they also worked simultaneously at NeoEdge Networks, Inc as a Senior Software Developer, where they created an Ad Server and worked on a customized installer used by Microsoft and Yahoo. In 2011, they joined FreshBooks as a Software Developer and worked there until 2015. Chris's most recent position is at Points, where they have held various roles since 2015, including Team Lead, Technical Team Lead, and currently, Director of Engineering.

Chris Sheppard attended the University of Waterloo from 1993 to 1998, where they pursued a Bachelor of Applied Science (BASc) degree in Mechanical Engineering.