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Wallace (Wally) Trenholm has had a varied career in the technology industry. Wallace (Wally) began their professional journey in 1995 in an unspecified role. In 1997, they became the Founder and Chief Technology Officer of Epoch Integration Inc. Wallace (Wally) held this role until 2009, when they founded Sightline Innovation Inc, where they served as Chairman. In 2020, they joined the Centre for International Governance Innovation (CIGI) as a Senior Fellow.

Wallace (Wally) Trenholm's education history includes a B. Sc. in Computer Science from Western University between 1993 and 1997. In 2006 to 2010, they earned a Commercial Pilot License - Aeroplane from Canadian Flyers and Diamond Flight Centre, Transport Canada - Group 1 IFR. From 2009 to 2011, they attended Mauna Loa Helicopters and Helicopter Acadamy for FAA Student Pilot - Helicopter. In 2011, they completed a Project Management Professional course from Project Management Institute.