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Dennis Outlaw has a diverse work experience, starting in 1988 as a part-time supervisor at United Parcel Service. From 1994 to 1995, they worked as a Graphic Design Artist at Ameritech. Dennis then joined Ross Roy Communications in 1995 and served as a Desktop Document Technician before becoming a Project Leader from 1996 to 1999. Dennis Outlaw then worked at BBDO Detroit as a Senior Art Director from 1999 to 2009, and later joined Union Adworks in 2010, holding the position of Senior Art Director.

Dennis Outlaw attended Eastern Michigan University from 1989 to 1992, where they pursued a Bachelor of Fine Arts degree in Graphic Design.