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

Strong 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

Strong compensation

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📌 Chief Technology Officer (Winnipeg)
🏢 AimHire
📍 Winnipeg