Our client is a
well-established Canadian legal services business, combining legal expertise, technology, and AI to transform the consumer legal experience.
They’re looking for a
hands-on, product-minded CTO
to lead product and engineering and build an AI-native platform for the next phase of growth.
What You’ll Do
Lead product and engineering for an AI-native platform
Own product strategy, roadmap, and technology
Build scalable AI-powered workflows and client experiences
Hire and grow a high-performing engineering team
Stay hands-on with architecture and development
Partner closely with the CEO and leadership team
What We’re Looking For
5+ years in engineering/technology leadership
Startup CTO, co-founding CTO,



or 0→1 engineering leadership experience
Strong product judgment and technical depth
Proven experience applying AI/LLMs to real-world workflows
Must be based in / able to work hybrid from Toronto
Why Join?
Profitable, established business with
startup speed
100,000+ clients
and a massive built-in audience
Solid growth with
AI-driven margin improvement
Prospect to help build
one of Canada’s largest consumer law businesses
Significant end-to-end ownership across product and technology
Robust compensation
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📌 Chief Technology Officer Winnipeg
🏢 AimHire
📍 Winnipeg