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Robert Wakefield has a diverse work experience history. Robert started their career at Onward Manufacturing as a Graphic Designer from January 2002 to October 2005. Robert then worked as a Graphic Designer at Snowbear Limited from October 2004 to April 2007, followed by a role as a Senior Designer at Ampersand Studios from April 2007 to September 2008.

In September 2008, Robert joined Copp Communications as a Graphic Designer until March 2011. Robert then worked as an Interactive Media Designer at Protiviti from March 2011 to November 2012, primarily involved in Adobe Flash and Photoshop development for electronic learning modules.

From November 2012 to November 2014, Robert worked as an Instructional Digital Media Developer at the University of Waterloo, creating digital assets for online courses. After that, they joined Conestoga College Institute of Technology and Advanced Learning as a Frontend Web Developer in December 2014. In this role, they were responsible for developing the college's online courses and collaborating with various stakeholders to ensure high-quality and interactive learning experiences.

Alongside their professional career, Robert also worked as a Host for the Accidental Survivors Podcast from 2006 to 2016, discussing topics related to new media, games, books, and movies. Overall, Robert's work experience highlights their proficiency in graphic design, multimedia development, and instructional digital media.

Robert Wakefield has a diverse education history. In 2010, they obtained a Certificate in Advanced ActionScript 3 from Conestoga College. Prior to that, from 1993 to 1996, Wakefield pursued a degree in Illustration from Sheridan College. Robert also attended Seneca College from 1991 to 1993, where they studied Television Production as part of a degree program in Radio and Television Production. Wakefield's secondary education was completed at Grey Highlands Secondary School from 1986 to 1991. Lastly, their earliest known education experience was at MacPhail Memorial from 1977 to 1985, though no specific degree or field of study was mentioned.