About the Role

Lead and grow the engineering organization at a legal services company building AI-enabled tools for consumer legal workflows. You will guide technical direction across client-facing platforms, internal systems, and services that support multiple practice areas.

What You'll Do

- Hire, develop, and manage a high-performing engineering team, with a focus on engineering talent.
- Improve engineering velocity and deliver dependable, high-quality releases against business priorities.
- Own technical direction for client portals, case management, internal tools, publishing, partnerships, payments, data, and IT.
- Build AI-enabled workflows that reduce manual effort across immigration services.
- Set engineering standards, create clarity and accountability, and support team autonomy.
- Partner closely with Product to ship useful products and contribute hands-on when needed.

What We're Looking For

- Five to ten years of software engineering experience, including engineering leadership.
- Experience recruiting, mentoring, and managing technical teams,



and building teams focused on higher output.
- Solid technical depth and product judgment, with experience making architectural decisions and shipping customer-facing products.
- Applied AI experience, including automating workflows and demonstrating measurable productivity gains.
- Experience with Node.js, TypeScript, React or Next.js, PostgreSQL, and Google Cloud Platform; Python and FastAPI experience for AI or document processing is beneficial.
- Experience in small teams with broad ownership and building platforms that support multiple products or business lines.
- A degree in Computer Science or Engineering is preferred. Legal experience is not required.
- Must be authorized to work in Canada without visa sponsorship.

Compensation & Benefits

Base salary: CAD $200,000 to $230,000 annually. Visa sponsorship is not available.

Location

Hybrid role based in Toronto, Ontario, Canada.

📌 Head of Engineering (Toronto)
🏢 Wintermeyer Ventures
📍 Toronto