Chief Technology Officer (Toronto, CAN)
- Compensation
- CA$275K–CA$350K
- Work mode
- Hybrid/On-site
- Location
- Toronto, ON, Canada
- Industry
- Legal Technology
Your market value for this role
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The mandate
We are looking for a Chief Technology Officer with 5+ years of experience to own product and engineering for the organization AI-native consumer law platform. We want a scrappy, product-minded builder who will run their own domain. AI has changed the economics of consumer legal services, and this person will build the platform that takes us from immigration to every area of consumer law as we become Canada's largest consumer law business. You'll get startup speed and ownership, backed by a profitable 50-year-old company that has served 100,000+ clients.
Key responsibilities
- Building out the organization+ (our client portal and case-management platform) so it's AI-native across all 5 immigration practice areas. The goal is for 100% of new matters to run through AI-native workflows within a year.
- Owning the product roadmap: sorting through feature requests from lawyers, case managers and thousands of clients, and picking the ones that help us serve clients smarter, better and faster.
- Owning the client portal as a product in its own right, with a target of a 4.8/5 client experience rating.
- Building a scalable platform that can take on other law firms as we acquire them and expand into new areas of consumer law.
- Hiring and growing a team of strong engineers, plus product, design and data capabilities, while staying hands-on yourself.
- 5+ years of experience. We'll make exceptions for standout people, such as a founder who built, scaled and sold a business.
- Experience as a startup CTO, co-founding CTO, or engineering leader who has owned product in a 0-to-1 environment, and who is willing to get their hands dirty. First-time CTOs are welcome.
- Strong product judgment, with a track record of setting priorities and building roadmaps across many competing stakeholders.
- Proven experience making AI useful in real-world workflows, and enough technical depth to code directly when needed (the interview process includes a coded project lasting about a week).
- Genuine interest in consumer law and legal services. No legal background is required. Must be able to work hybrid in Toronto.
What you bring
- 5+ years of experience. We'll make exceptions for standout people, such as a founder who built, scaled and sold a business.
- Experience as a startup CTO, co-founding CTO, or engineering leader who has owned product in a 0-to-1 environment, and who is willing to get their hands dirty. First-time CTOs are welcome.
- Strong product judgment, with a track record of setting priorities and building roadmaps across many competing stakeholders.
- Proven experience making AI useful in real-world workflows, and enough technical depth to code directly when needed (the interview process includes a coded project lasting about a week).
- Genuine interest in consumer law and legal services. No legal background is required. Must be able to work hybrid in Toronto.
Location & engagement details
Toronto, ON, Canada · Hybrid
Base salary: C$275,000 – C$350,000, depending on experience. Annual bonus: The target is 50% of base. Goals are set together with the CEO and are meant to be realistically achievable (e.g., moving new matters onto AI-native workflows and a 4.8/5 client portal rating). That puts on-target earnings at about C$412.5K – C$525K. Equity: the organization is a family-owned business, so equity is offered as a phantom ("ghost") equity package.; Equity: Competitive equity; Visa sponsorship details: Not open to any visas (e.g. US the organization, Green Card holders); Hybrid work policy: 3 days in-office in Toronto, ON (the company is moving to a bigger office soon, and in-office days may increase)
About this mandate
This is a live c-suite search with direct introductions to the hiring team. The role sits in legal technology and is located in Toronto, ON, Canada on a hybrid/on-site basis, with compensation of CA$275K–CA$350K.
This is a confidential search. Read the brief above, then apply below for this role. The company name is shared once there's a close match and mutual interest.
Most senior mandates are filled this way — privately, before any listing exists. Read how unadvertised executive roles actually get filled.
- This is a confidential search. The company name and full role details are only discussed on a call with one of our recruiters if there is a close match.
- We use your details — your LinkedIn profile URL and email address — to match you against this mandate and any other closely matched roles.
- A verifiable email address, LinkedIn profile and a recent PDF resume are required. Submissions from bots, spammers or unverifiable profiles are removed.
- There is no call booking at this stage. Calls are scheduled only after we identify a close match.
Who can apply
- C-suite, EVP/SVP, VP and Head of function leaders
- Proven scale-up, venture-backed or enterprise leadership experience
- Track record of building and leading teams in the relevant function
Final hiring decisions rest solely with the hiring company. Outcomes depend on role availability and decisions made by the hiring team.
Apply — Chief Technology Officer (Toronto, CAN)
This application is for this role only. It is reviewed against the brief above, and you will be contacted if there is a close match.
- This is a confidential search. The company name and full role details are only discussed on a call with one of our recruiters if there is a close match.
- We use your details — your LinkedIn profile URL and email address — to match you against this mandate and any other closely matched roles.
- Handled confidentially — your details are never shared without your consent.
- A referral is an introduction, not a guarantee of an interview or an offer.
- Final hiring decisions rest with the hiring company; outcomes depend on role availability and their decisions.