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Rob Bennet has worked in various roles since 2004. Rob began their career as a Designer at Elemental Design in 2004. In 2006, they worked as a Marketing Analyst at Macy's Corporate Marketing. From 2008 to 2009, they held positions as an Editor/Designer/Copywriter at Juggle, Promotions Director/Web Designer at South Central Media, and a Technologist at InteliSpend. From 2011 to 2013, they were the Owner of Houndstooth and Co-Founder & CTO of Pixel Press. Rob then served as Co-Founder & CEO of Pixel Press Technology, LLC from 2013 to the present.

Rob Bennett attended the University of Tennessee, Knoxville from 2001 to 2006, where they earned a Bachelor of Science degree in Psychology.