Jobs in Vaughan

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Within 25 km of Vaughan

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Chief Technology Officer, AI-Native Consumer Platform
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Calliere

Chief Technology Officer, AI-Native Consumer Platform

Toronto, ON, Canada

Full-time

Within 25 km of Vaughan · About 22.9 km from the city centre

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Job details

Job type: Full-time
Posted: Oct 7, 2026

Original job description

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.

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More about this job

Responsibilities

Lead the transformation of the client portal and case management platform into an AI-native engine across all practice areas. Manage the product roadmap, hire and scale the engineering and product teams, and ensure the platform supports business expansion.

Requirements

Requires 5+ years of experience as a startup CTO or engineering leader with a proven track record in product ownership. Candidates must be hands-on with coding and have experience implementing AI in real-world workflows.

Skills

Artificial Intelligence
Product Management
Engineering Leadership
Node.js
TypeScript
React
Next.js
PostgreSQL
Python
FastAPI
PHP
Google Cloud
LLMs
Software Architecture
Team Building

Visa sponsorship

Not detected in the job text

Keywords

Chief Technology Officer
AI-Native
Consumer Platform
Legal Services
Node.js
TypeScript
React
Next.js
PostgreSQL
Python
FastAPI
PHP
Google Cloud
LLMs
Product Roadmap
Engineering Management
Case Management
Startup
0 to 1
Software Engineering
Data
Design
Platform Development
Legal Tech

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