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Ray Skaff started their work experience in 1991 at Rogers Communications, where they held various roles including Station Manager and National Manager of Captioning Services. Ray oversaw teams, improved brand and customer relationships, and managed programming projects. In 2001, they worked as a Professional Consultant, providing professional services to organizations and businesses. From 2014, they joined Gabriel Pizza Franchise Corporation as the VP of Corporate Affairs & Public Relations. Ray also worked as the Director of Programming at Cable Public Affairs Channel in 2001.

Ray Skaff attended Algonquin College of Applied Arts and Technology from 1981 to 1983, studying Television & Radio Broadcasting. Ray later returned to the same college to complete a degree in Radio & Television Arts, with a focus on Radio and Television.