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Jonathan Evans began their work experience at Sun International in 1998 as a Project Manager. Jonathan then went on to hold roles such as Gaming Systems Business Consultant, System & Dev Manager, and GM: System Development & Integration. In 2009, they joined OLG as the Vice President of Gaming/Bingo IT. Jonathan later transitioned to the role of Vice President of IT Strategy & Architecture and currently serves as the Vice President of Digital Engineering and Operations.

Jonathan Evans has a diverse education history. Jonathan attended the University of Toronto - Rotman School of Management in 2009 for an Executive Program in Leading the Way. In 2001, they pursued Executive Management Development at the Graduate School of Business at the University of Cape Town. Prior to that, between 1993 and 1994, they obtained a National Higher Diploma in Information Technology from Cape Peninsula University of Technology. In 1990 to 1992, they completed a National Diploma in Computer Data Processing from the same institution. Jonathan also attended St. Albans College from 1985 to 1989, although no specific degree or field of study was mentioned for that period. Jonathan obtained additional certification in the Governance of Enterprise IT (CGEIT) from ISACA in 2012.