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Aimhire

Chief Technology Officer

Toronto, ON, Canada

Full-time

Apply About employer

Applications open in a new tab.

Job details

Job type: Full-time
Apply by: Dec 3, 2026
Posting language: English
Posted: Nov 3, 2026

Original job description

🚀 Hiring: Chief Technology Officer (CTO) | Toronto, Canada

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.

📍 Toronto, ON - Hybrid (3 days/week)

💼 Full-time | Law & AI

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
Hands-on, entrepreneurial mindset
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

Tech: Node.js, TypeScript, React, Next.js, PostgreSQL, Google Cloud, Python, FastAPI, AI/LLMs

📩 Interested? Reach out to us to learn more.

Apply About employer

More about this job

Responsibilities

Lead product and engineering for an AI-native platform, owning product strategy, roadmap, and technology while building scalable AI-powered workflows and client experiences. Hire and develop a high-performing engineering team, remain hands-on with architecture and development, and partner closely with the CEO and leadership team.

Requirements

Requires at least five years of engineering or technology leadership experience, with startup CTO, co-founding CTO, or 0-to-1 engineering leadership experience. Candidates should have strong product judgment and technical depth, practical experience applying AI or large language models to real-world workflows, an entrepreneurial mindset, and the ability to work hybrid from Toronto.

Skills

Product Strategy
Technology Roadmapping
Engineering Leadership
AI
Large Language Models
AI-Powered Workflows
Software Architecture
Software Development
Team Building
Node.js
TypeScript
React
Next.js
PostgreSQL
Google Cloud
Python

Visa sponsorship

Not detected in the job text

Keywords

Chief Technology Officer
Product Strategy
Product Roadmap
Engineering Leadership
AI-Native Platform
Artificial Intelligence
Large Language Models
AI-Powered Workflows
Client Experiences
Software Architecture
Software Development
Startup
0-to-1 Leadership
Legal Services
Consumer Law
Node.js
TypeScript
React
Next.js
PostgreSQL
Google Cloud
Python
FastAPI
Toronto

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