Chief Technology Officer

Aimhire; Toronto; Hybrid; CAD 180,000 - 280,000; Full time

Benefits offered by this job

Startup speed

Large client base

AI-driven margin improvement

End-to-end ownership

Hybrid work in Toronto

Job summary

Aimhire is partnering with a well-established Canadian legal services business to hire a hands-on, product-minded CTO in Toronto. You will lead product and engineering for an AI-native platform, owning strategy, roadmap, and technology to drive growth.

You will build scalable, AI-powered workflows, work closely with the CEO and leadership team, and manage a high-performing engineering team while staying hands-on with architecture and development.

Qualifications

• 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.

Responsibilities

• 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.

Job description

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
• Opportunity to help build one of Canada’s largest consumer law businesses
• Significant end-to-end ownership across product and technology
• Strong compensation