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Robert O'Brien has a diverse work experience spanning multiple roles and companies. Robert began their career as a Senior Graphic Designer at The Marketing Store, North America in 1998. Robert then worked as a Freelance Art Director at Draft Worldwide in 2001, where they developed new point of purchase (P.O.P) materials. In 2003, they joined CompTIA as a Senior Designer, and in 2008, they worked as a Freelance Senior Art Director at Nielsen. From 2009 to 2014, they served as a Senior Art Director at DeVry University, and then transitioned to the role of Associate Creative Director until 2016. Currently, they are employed as the Creative Director at Body-Solid, Inc. since April 2016.

Robert O'Brien has a Master of Business Administration (M.B.A.) in Marketing from Keller Graduate School of Management. Robert also holds a Bachelor's Degree in Graphic Design from Eastern Illinois University. In addition, they have studied Photography at Columbia College Chicago. Robert has obtained a Six Sigma - Yellow Belt Certification in 2015. Robert pursued further education with a Master of Business Administration - MBA in Marketing from Keller Graduate School, which was completed between 2009 and 2014. Robert also has obtained additional certifications including Brand Strategy for Designers, Content Creation: Strategy and Tools, and Social Media Marketing: Strategy and Optimization from LinkedIn, with the most recent being in 2023.