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Jamie Playfair started their work experience in 1991 as a Graphic Designer at Target Marketing-Richards Media. From 1992 to 2002, they worked as a Graphic Designer at Advocate Communications Group. In 2002, Jamie joined Advocate Creative Group as an Art Director and later became the Creative Director in 2012. Most recently, in 2022, they joined Velsoft Training Materials as a Creative/Art Director.

Jamie Playfair attended Saint Mary's Academy.