DT Toronto, ON (Hybrid, 3 days in office) | Full-time
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.
Skills Required
- 5+ years as a startup CTO, founding CTO, or engineering leader who owned product in a zero-to-one setting
- Strong product judgment and experience setting priorities among competing stakeholders
- Experience making AI useful in real workflows
- Ability to write code; the hiring process includes a coded project of approximately one week
- Curiosity about consumer law and legal services
- Ability to work hybrid in Toronto
- Experience building, scaling, and selling a company
What We Do
Calliere is a boutique professional and executive recruitment and advisory firm that helps organizations build high-performance teams. It specializes in sourcing leadership, engineering, data science and AI, healthcare technology, infrastructure, telecom, sales, and business-development talent. The firm serves clients across technology, fintech, healthcare, life sciences, infrastructure, and other sectors through a personalized, thorough, results-driven approach tailored to each client's specific hiring and organizational needs.
