Head of Engineering

*hiring on behalf of our client

Title: Head of Engineering

Time: Full-Time

Location: Hybrid (Toronto, ON, Canada)

Compensation: CA$200K - CA$230K (OTE: CA$320K - CA$350K)

The Company

Our client is a premier full-service Canadian immigration law firm and online legal platform. Operating since 1976 and establishing an early, pioneering web presence in 1994, they offer a wide range of tools, resources, and one of the largest global discussion forums in the space. The organization is actively scaling an AI-native platform designed to modernize and transform consumer legal services, beginning with Canadian immigration and expanding into other consumer law disciplines.

Role Overview

Our client is seeking a Head of Engineering with 5 to 10 years of software engineering experience to build and scale a high-velocity engineering organization. In this leadership role, you will take ownership of the technical direction for the client portal, case management systems, internal workflow tools, publishing channels, data integrations, and IT infrastructure. You will partner closely with executive leadership to deploy AI-native workflows that significantly reduce manual human processing, optimize delivery standards, and mentor a top-tier engineering team.

Key Responsibilities

• Recruit, develop, and lead a high-performing engineering organization focused on developer growth and execution.

• Drive engineering velocity, establishing dependable delivery processes and turning high-level priorities into reliable, high-quality releases.

• Own overall technical architecture and systems direction for the core client portal, case management platform, internal automation tools, publishing infrastructure, partnerships, payments, and data systems.

• Design and implement AI-native workflows that automate document processing and streamline operations across five core immigration practice areas.

• Set clear engineering standards and best practices while remaining capable of contributing hands-on to solve complex technical challenges.

• Partner closely with Product and executive leadership to align technical roadmap milestones with strategic business objectives.

• Report directly to the CEO, with the opportunity to transition into or work alongside an executive CTO role as the company scales.

Qualifications

• 5 to 10 years of software engineering experience, including proven technical leadership and people management.

• Demonstrated track record of recruiting, mentoring, and retaining high-caliber technical talent across engineering disciplines.

• Strong technical depth and architectural judgment across modern web and cloud technologies, including Node.js, TypeScript, React, Next.js, PostgreSQL, and Google Cloud Platform (GCP).

• Practical experience implementing AI and LLM workflows, automated document processing, or Python/FastAPI backend services to generate measurable productivity gains.

• Proven ability to establish engineering rigor, accelerate release cycles, and deliver dependable production software.

• Exceptional communication and cross-functional leadership skills with an ability to provide clear team direction and maintain accountability.

• Ability to work in a hybrid capacity out of the Toronto, ON office.