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Ken Cummings has a diverse work experience spanning several roles and industries. Ken started their career as a Programmer at McPeek Computer Consulting in 1988 and later worked as a Consultant in the B.C. Information Technology practice at Coopers and Lybrand. In 1997, Ken joined Georgia-Pacific as a Senior Systems Analyst.

In 2004, Ken became the President of Salient Systems LLC (DBA "Trivoca Consulting"), where they ran a full-time I.T. consulting business. During their time at Trivoca, Ken led various technology consulting and staff-augmentation engagements for AutoTrader, Kelley Blue Book (KBB), and their parent company Cox Automotive.

In 2016, Ken joined Trainz.com as a Principal Technical Architect, overseeing an offshore development team and an onshore KTLO/desktop support team. Ken also took on the role of Head of Marketing in 2018. Ken's responsibilities at Trainz.com included acting as the product owner for custom-built software and primarily managing back office applications.

Currently, Ken is the Chief Technology Officer at Trainz.com, a position they assumed in January 2023. As CTO, they are responsible for leading the company's technological advancements and strategies.

Ken Cummings attended Camosun College from 1985 to 1987. In this period, they studied Computer Technology and also specialized in Computer/Information Technology with a focus on Business. However, they did not obtain a specific degree during their time at the college.