Chief Technology Officer, AI-Native Consumer Platform

DT Toronto, ON (Hybrid, 3 days in office) | Full-time

The opportunity

AI has changed the economics of consumer legal services, and our client wants to be the company that proves it. They're a profitable, family-owned legal services business with decades of history and a very large client base behind them. Now they want a CTO who will turn their client platform into an AI-native engine and use it to become the largest consumer law business in Canada.

You get startup speed and real ownership, with none of the fundraising anxiety. The business is already profitable, the clients are already there, and the CEO wants someone to run their own domain.

What you'll do

• Make the client portal and case management platform AI-native across every practice area, with the goal of running 100% of new matters through AI workflows within a year
• Own the product roadmap and decide which requests from lawyers, case managers and thousands of clients actually matter
• Treat the client portal as a product in its own right and push it to a 4.8/5 client rating
• Build a platform that can absorb acquired law firms and expand into new areas of consumer law
• Hire and grow the engineering team, plus product, design and data, while staying hands-on yourself

Requirements

Who you are

• 5+ years as a startup CTO, founding CTO, or engineering leader who has owned product in a 0 to 1 setting. First-time CTOs are welcome, and a founder who has built, scaled and sold a company will get a serious look even with less time
• Strong product judgment and a record of setting priorities across a lot of competing voices
• You've made AI genuinely useful in real workflows, and you can still write the code yourself (the process includes a coded project of about a week)
• Real curiosity about consumer law and legal services. No legal background needed
• Able to work hybrid in Toronto. Visa sponsorship is not available

Stack

Node.js, TypeScript, React, Next.js, PostgreSQL, Python, FastAPI, PHP, Google Cloud, LLMs

Benefits

Compensation

Very strong base depending on experience, a 50% target bonus tied to goals you set with the CEO, and more.

If you want to build something that changes how everyday people get legal help, let's talk. Confidential inquiries welcome.