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Jason Cheshire began their work experience in 1999 as a Senior Designer at Hartford Advocate. Jason then moved on to W&T Graphix in 2002, where they served as Lead Designer until 2008. In the same year, they joined GO as an Art Director and later became the Creative Director in September 2019.

From 1995 to 2000, Jason Cheshire attended Keene State College and earned a Bachelor of Science (B.S.) degree in Graphic Design.