Director of Engineering in Toronto

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.

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.

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 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:

• 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.
• 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.
• 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 bar.
• Creating clarity around ownership, mandates, interfaces, and platform boundaries across pods.

What You Offer:

• 10+ years of hands-on experience designing and building heavily used customer facing SaaS products.
• 5+ years of engineering leadership experience, including responsibility for multiple teams or engineering managers.
• Evidence that you have helped shape innovative products and technical direction in partnership with Product and Design.
• Strong architectural foundation with experience owning complex systems end-to-end.
• Ability to design and reason about scalable distributed systems, including performance, reliability, consistency, and cost tradeoffs.
• Demonstrated ability to operate as a senior level IC when needed.
• Track record of identifying critical issues, setting clear goals, and shaping the technical strategy for engineering organizations.
• Experience aligning engineering, product, design, and legal research around shared outcomes and coordinated execution.
• Clear communication skills with the ability to explain complex system designs to technical and non-technical audiences.
• Experience guiding teams through architectural decisions, refactors, and long-term platform modernization.

Additional Experience That Would Be Valuable:

• Experience with product-led growth, customer activation, experimentation, conversion, engagement, or retention.
• Experience building enterprise authentication, authorization, permissions, account structures, collaboration, billing, or purchasing systems.
• Experience using product analytics and experimentation to guide technical and product decisions.

Technologies You Can Expect To Work With:

• Node.js, React, TypeScript, Python
• AWS, Cloudflare, Terraform
• Kubernetes with ArgoCD, Docker
• GitHub, CircleCI
• PostgreSQL, ElasticSearch, DynamoDB, S3
• Kafka

What We Offer You:

• A meaningful leadership role shaping the platform foundation of a fast growing company.
• A mission-driven culture where your work directly advances clarity, efficiency, and accessibility in tax research.
• Competitive base salary, stock options, and benefits designed to support you and your family.
• Flexibility in how you work: primarily remote, with occasional travel to our Toronto office.
• A collaborative, ambitious, and supportive team that values innovation, respect, and fun.
• The excitement of a fast-growing, well-funded company with clear momentum, and the resources to back bold initiatives.

The Core Values that Define Our Culture:

• We are customer-focused.
• We put team over self.
• We are pleasant and playful.
• We are open to better ideas.
• We move fast and fix things.

What to Expect in the Interview Process:

We anticipate a high volume of applicants for this role and are excited to grow our team. A human will review each application and get back to you as soon as possible. We appreciate your patience and look forward to connecting with you!

Interview Process:

• Chat with Elli, our Talent Acquisition Manager.
• Meet our VP of Engineering, Mario.
• Technical Deep Dive with an Engineering Team Member.
• System Design Exercise.
• Leadership interview with our VP of Engineering, Mario.
• Meet our CTO, Brett.
• Meet our CEO, Ben.

We believe our strength is built on diversity of thought, and encourage candidates from all backgrounds and experiences to apply. We value inclusiveness and are an equal opportunity employer. We do not discriminate based on race, religion, colour, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

We strive to create an inclusive and accessible hiring experience for all candidates. If you need any accommodations during the interview process, please let us know in your application. Our team is dedicated to providing the necessary support and making reasonable adjustments to ensure a smooth process for everyone.

This is a Level 6 in Blue J’s career level framework. We use levels to define the expected scope, autonomy, impact, decision-making, and experience for each role. Final compensation will be set fairly and thoughtfully based on experience, expertise, and alignment with the role’s responsibilities.