Director of Engineering Remote, Ontario

Technology

Remote

Full time

About Blue J Blue J is the leading generative AI solution for tax professionals and one of Canada's fastest-growing AI companies. Headquartered in Toronto, we're a high-growth B2B SaaS company building industry-leading tax research software that helps accountants find accurate answers to complex tax questions with greater speed and confidence.

Backed by a $122M USD Series D funding round, we're scaling rapidly across North America and the UK while continuing to push the boundaries of what's possible with AI. By combining advanced technology with deep tax expertise, we empower tax professionals to work more efficiently, make better decisions, and deliver greater value to their clients.

A Note on Location Primarily remote, but you must live within driving distance of our Toronto office. You’ll join us in person for every quarterly and occasionally for team get-togethers (typically 1–3 visits per quarter).

To help you get off to a great start, we bring all new team members together for their first three days of onboarding. If you’re based outside of our local commuting area, Blue J will arrange and cover your travel and accommodation.

About the Team Blue J’s technology creates value when tax professionals can easily discover, trust, and incorporate it into their work. The Tax Pro Engagement pillar owns that experience, including onboarding, search, collaboration, account management, purchasing, integrations, and core customer workflows.

As Director of Engineering, you will set the pillar’s technical and organizational direction, lead multiple product-engineering teams,



and partner with Engineering and Product leadership to shape priorities and measure customer value.

You will initially immerse yourself in our product, architecture, customers, and codebase while contributing to technical design and complex problem-solving. Over time, your focus will shift toward scaling the teams, leaders, systems, and practices supporting the pillar.

The Opportunity We are looking for a Director of Engineering that will guide the evolution of Blue J’s platform architecture and help our engineering teams deliver high quality products at speed. This role is ideal for someone who is a strong system designer, deeply experienced with building SaaS platforms, and energized by helping teams navigate technical complexity.

The ideal leader combines deep systems expertise with strong product instincts and a genuine commitment to user experience. They will champion the end user, challenge assumptions, and help identify new product possibilities that may not yet be obvious.

You will work closely with product, engineering, and research to define product direction, build reliable and scalable systems, and ensure our teams have the tools and infrastructure they need to ship confidently and frequently. This leader will coach senior engineers, help untangle difficult architectural challenges, jump into code and designs when needed, and grow a team made up of strong software engineers.





This role is designed for a technical leader who enjoys building, mentoring, and shaping the foundational platform that enables world class product development.

What You’ll be Doing Setting Direction

Using customer insight, product metrics, and experimentation to guide priorities, evaluate product decisions, and continuously improve the user experience

Collaborating with product and engineering leaders to define goals and priorities

Tying engineering work to measurable outcomes such as activation, adoption, engagement, conversion, retention, workflow completion, performance, and customer trust

Owning the long term vision for platform capabilities that support reliability, scalability, developer experience, and speed of delivery

Identifying focus areas to improve architecture, infrastructure, system performance, and cross team technical alignment

Enabling High Quality Delivery

Leading platform engineers to design and build foundational systems and internal tools

Going deep into architecture and designs to guide teams through ambiguity and complexity

Helping engineers make architectural tradeoffs that balance speed with long term maintainability

Ensuring projects stay on track and are communicated clearly to stakeholders

Supporting teams in shipping frequently, safely, and with high confidence, consistent with Blue J’s engineering culture

Strengthening the Engineering Organization

Coaching and developing engineers into strong system thinkers and leaders

Improving engineering practices that support quality, lean iteration, strong testing, and healthy system design

Hiring high performing engineers and engineering managers who raise the

📌 Director of Engineering (Winnipeg)
🏢 Blue J Legal
📍 Winnipeg