James Cheng

About

James Cheng is a software consultant, entrepreneur, and ecosystem builder with a decade of experience leading digital transformation across aviation, finance, healthcare, and the public sector. He has returned to Canada to contribute to the Waterloo ecosystem, supporting AI-first entrepreneurship through work-integrated learning, community building, and venture development.

At Waterloo, he studied Systems Design Engineering and began exploring venture creation through the Velocity Residence. After graduating in 2014, he joined Pivotal Labs in Toronto before relocating to Singapore in 2017, where he continued through the VMware acquisition and developed a track record delivering workshops and speaking at SUTD and Taiwan DDD. He returned to Canada in 2025.

Current work

His current work spans three areas:

Venture Development and Applied Learning

Supporting students and early-stage founders in building ventures under real conditions, with a focus on AI-first thinking and applied problem solving.

Community and Ecosystem Building

Connecting founders, students, and operators across education and industry to build the collaborative infrastructure that sustains regional innovation.

AI-First Enterprises

Helping organisations and ventures translate AI capabilities into deployable systems, from workflow redesign to automation in traditional industries.

Education

• BASc, Systems Design Engineering, University of Waterloo, 2014
• Exchange, TU Braunschweig, Germany, 2012
• MBET, University of Waterloo, 2026

Experience

• Pivotal Labs and VMware, Software Engineer to Staff Software Engineer, Toronto and Singapore, 2014–2024
• Teaching Assistant, Enterprise Co-op, University of Waterloo, 2025–present
• Co-founder, Divotron, 2025–present