Director of Technology

About the role
We’re looking for a senior software engineering leader to help us modernize our platform, evolve our systems, and transform how we build, ship, and support software at scale. This role goes beyond feature delivery — it’s about rebuilding the foundation of our technology stack so it’s simpler, faster, more reliable, and deeply aligned with how we serve our customers.

You’ll work hands-on with engineering teams and collaborate closely with product, design, and support to address key challenges — including technical debt, outdated frameworks, bloated workflows, and fragmented systems. You’ll bring strong software development experience to the table, with the judgment and vision to architect long-term solutions that don’t just work internally, but also improve the end-to-end customer experience.

This is a leadership role for someone who is deeply technical, customer-aware, and ready to roll up their sleeves to guide teams through high-impact change.

Key Responsibilities

Software Architecture & Modernization

• Lead the audit, refactor, and replacement of legacy code and frameworks.
• Consolidate and simplify over 200+ codebases into a more modern, maintainable architecture.
• Drive decisions on programming languages, frameworks, libraries, and design patterns — with a strong bias toward developer productivity and customer reliability.
   

Hands-On Technical Leadership

• Write, review, and guide production-grade code — with a focus on backend systems and integration layers.
• Set and uphold coding standards, testing practices, and architectural consistency across teams.
• Mentor engineers across the org on best practices, code clarity, and long-term thinking.
   

Developer Experience & Engineering Effectiveness

• Identify friction in the development lifecycle and lead efforts to streamline workflows, environments, and automation.
• Improve onboarding, documentation, and tooling so teams can build and ship with confidence and speed.
• Ensure CI/CD systems are robust, fast, and easy to maintain.
   

Customer-Facing Impact & System Reliability

• Design systems with the end user in mind — ensuring uptime, responsiveness, and usability are not compromised by architectural decisions.
• Evaluate technical debt not just for internal complexity, but for how it affects customer-facing teams, support agents, and product outcomes.
• Use engineering to proactively reduce support burden and improve customer satisfaction.
   

Cross-Team Collaboration & Strategic Influence

• Partner with product, support, and operations to surface pain points that impact customers or delivery velocity.
• Translate engineering risks into clear business tradeoffs for leadership stakeholders.
• Help define an engineering roadmap that supports business growth, reduces churn, and reinforces platform stability.

Who You Are

• 6+ years of experience in software development, including deep hands-on work with modern application stacks (e.g., Node.js, .NET, Python, or similar).
• 3+ years of experience in a software architecture or engineering leadership role in a platform- or infrastructure-heavy environment.
• Proven track record of refactoring complex systems, managing technical debt, and building for performance, scale, and stability.
• Strong communicator with the ability to influence non-technical stakeholders and inspire teams.
• Comfortable leading change across teams, especially in high-stakes or legacy-heavy environments.
• A champion of customer-first engineering — where uptime, clarity, and reliability are seen as product features.

Why This Role Matters

We’re not here to do business as usual. Rebel is in the thick of a reinvention—rolling up our sleeves, rethinking how we work, and building smarter, more scalable solutions. It’s a little messy, a lot exciting, and full of possibility. We’re looking for a Director of Technology who’s not just here to run systems—but to help shape the future.

If you’ve got an entrepreneurial mindset, a sharp eye for what needs fixing (and the follow-through to do it), and a hunger to lead through change, this might be your kind of place.

This is a seat at the leadership table. You’ll have real influence in our growth strategy, a voice in shaping how we scale, and the trust to drive meaningful change—not from the sidelines, but from the centre.

We value quiet confidence over ego, action over talk, and kindness with a little edge. If even part of this sounds like you, we’d love to start a conversation.

• Opportunity to shape the future of a proudly Canadian brand in a competitive global industry
• Autonomy and ownership to build strategies from the group up
• A collaborative, supportive, and entrepreneurial culture
• Competitive salary and benefits
• Centrally located office  - we are located in the Byward Market