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Robert Pingitore has work experience as an Art Director at St. Joseph Communications since January 2019. Before that, they worked as a Creative Lead at Design Garage starting in November 2013. Robert also has experience as a Layout Artist at Rogers Media from April 2016 to March 2018. Prior to that, they worked as a Graphic Designer at MMK Marketing from November 2015 to April 2016, at Totem from August 2014 to November 2015, at Queue Media from February 2014 to August 2014, and at Bell Media as an Associate Graphic Designer from December 2011 to April 2012.

Robert Pingitore has a diverse education history. In 2006, they obtained an Art Fundamentals Certificate from Seneca Polytechnic. Robert later pursued a Bachelor of Design degree in Advertising at OCAD University from 2007 to 2011. In 2015, they took a continuing education course at OCAD University focused on "The Art of Typography".