Posted last month
Chief Technology Officer, AI-Native Consumer Platform
@ Calliere
Toronto, Ontario
Overview
Calliere is hiring a Chief Technology Officer for its AI-native consumer platform in downtown Toronto, a hybrid full-time role with three days in the office. The CTO will make the client portal and case management platform AI-native across every practice area, own the product roadmap, and build and grow the engineering, product, design and data teams. The posting states a very strong base salary depending on experience and a 50% target bonus tied to goals set with the CEO. Visa sponsorship is not offered.
Responsibilities:
- Make the client portal and case management platform AI-native across practice areas
- Own the product roadmap and prioritize client and lawyer requests
- Push the client portal toward a 4.8/5 client rating
- Build a platform that can absorb acquired firms and expand into new consumer law areas
- Hire and grow engineering, product, design and data teams while staying hands-on
Requirements summary:
- 5+ years as startup CTO, founding CTO or engineering leader
- Owned product in a 0 to 1 setting
- Strong product judgment across competing priorities
- Made AI useful in real workflows and can write code
- Curiosity about consumer law; no legal background needed
- Able to work hybrid in Toronto
Tools & skills
Source and dates
Source type not verified · zoho
- Employer posting date
- 2026-10-06
- First seen by our source
- 2026-10-09
- Source record updated
- 2026-10-10
These dates describe the source record, not a live verification that the employer is still hiring. Check the original posting.
Job details
| Seniority | Lead |
| Department | Software development |
| Experience | 5+ years |
| Manages people | Yes |
| Hours per week | 40 (estimated) |
| Work setting | Office |
| Position | Mostly sitting |
| Physical demands | physical low · computer high |
| Languages | English |
| Perks mentioned | Performance bonus |
Summary and details written by AI from the posting; the employer’s posting is the authority.
Calliere
Saved company profile
Historical company information from a saved The Jobs API profile (LinkedIn/Crunchbase fields). It is not live-verified; figures may have changed. Missing values remain unknown.
Full company description
The Callière Group is a boutique organization that provides tailored executive search, talent acquisition, and advisory services to meet the unique challenges our clients face. We pride ourselves on a collaborative approach. We partner with our clients to solve their most challenging talent acquisition and management needs. The Callière Group has a dependable foundation of recruiting Management Consulting, IT professionals and Management Executives from across industries with particular expertise helping organizations within the Professional Services; Financial Services; Retail and, Technology sectors. Our outcome based approach is built on ensuring alignment of stakeholder needs. Our job is to provide our clients with the right candidates for their strategic talent requirements as well as to provide top tier advisory services. The Callière Group approach is one that is built to minimize organizational disruption; collaboratively defines and articulates an organization’s specific talent needs; and, best positions organizations and candidates for success. The commitment to delivering results that organizations, employers and candidates demand and deserve is best achieved with Callière Group consultants. Consultants who have gained wisdom and foresight that can only come from direct Professional Services experience at all levels, ongoing training, and have significantly accrued time-tested experience in both successful and even unsuccessful project execution.
- LinkedIn followers
- 2,806
- People associated on LinkedIn
- 3
- Reported office locations
- 54, rue Le Royer Ouest, Montreal, Quebec H2Y 1W7, CA
- 500 King Street West, Toronto, Ontario M5V 1L9, CA
- 8 Faneuil Hall Marketplace, Boston, Massachusetts 02109, US
- Other recorded names
- Calliere
- Calliere Group
- Specialties
- Recruiting
- Technical Recruiting
- Consulting
- Headhunting
- Executive
- Infrastructure
- Development
- Automated Testing
- Mobile
- Security
- Big Data
- Artificial Intelligence
- Machine Learning
- DevOps
- Architecture
- Bioengineering
- Bioinformatics
- Digital Health
- Computational Biology
- Biostatistics
- LLM
- NLP
- Cryptography
- Fintech
- Ultra Low Latency Development
- Web3
- and Blockchain
- Profile identifies a recruitment agency
- Yes
The Callière Group is a boutique organization that provides tailored executive search, talent acquisition, and advisory services to meet the unique challenges our clients face. We pride ourselves on a collaborative approach. We partner with our clients to solve their most challenging talent acquisition and management needs. The Callière Group has a dependable foundation of recruiting Management Consulting, IT…
| Field | Value |
|---|---|
| Industry | Information Technology & Services |
| Company size | 2-10 employees |
| Headquarters | Montreal, Quebec |
| Organization type | Privately Held |
| Year founded | 2008 |
| Specialties | RecruitingTechnical RecruitingConsultingHeadhuntingExecutiveInfrastructureDevelopmentAutomated TestingMobileSecurity |
| Open jobs on Jobsy | 14 |
| View page |
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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