About the Role
We're looking for a transformational technical leader to drive a full-scale modernization of our platform, systems, and development practices. This isn't a role focused on feature delivery or agile rituals — it's about solving deeply rooted architectural challenges, optimizing infrastructure, reducing operational risk, and preparing our technology for scale.
You'll work across engineering, product, and operations to address the real pain points in our current stack — from aging frameworks and fragmented codebases to ballooning AWS costs and emergency-driven workflows.
This is a strategic and hands-on leadership role for someone who thrives in diagnosing complex technical environments and building pragmatic, future-proof solutions.
Key Responsibilities:

• Technology Modernization
  • Lead the evaluation and phased replacement of outdated technologies.
  • Develop a modernization roadmap with clear ROI, timelines, and risk mitigation.
• Architecture & System Design
  • Reassess our microservices architecture; explore alternatives like containers or hybrid models for better manageability and cost-efficiency.
  • Consolidate over 200+ fragmented codebases into maintainable, scalable systems.
• Infrastructure & Reliability
  • Upgrade critical infrastructure (DNS, servers, monitoring, automation).
  • Implement proactive incident detection, root-cause prevention, and system observability.
• Platform Efficiency & Developer Experience
  • Create and enforce testing standards and code quality guidelines across teams.
  • Streamline development workflows and reduce onboarding friction for engineers.
• Cloud Optimization
  • Audit current AWS usage; eliminate waste and optimize performance-to-cost ratios.
  • Develop long-term cloud cost control and scalability strategies.
• Customer Experience Support
  • Analyze customer support ticket trends; reduce technical friction points through smarter design, documentation, or automation.
  • Collaborate with product and support teams to improve self-serve capabilities.
• Tech Strategy & Governance
  • Conduct a full audit of tools, frameworks, and languages in use.
  • Recommend a standardized, forward-looking technology stack and skill plan.
  • Establish documentation, visibility tools, and change-tracking systems.
• Cross-functional Collaboration
  • Partner with product, design, marketing, and customer success to ensure infrastructure choices align with business goals.
  • Mentor and support other engineering leaders, without direct team management (unless desired).

Who You Are

• 8+ years of experience in software engineering, with 3+ years in architectural or platform leadership roles.
• Proven track record modernizing legacy systems and improving infrastructure at scale.
• Deep understanding of cloud platforms (especially AWS) and cost optimization strategies.
• Strong architectural background (monolith to microservices, containers, service orchestration, etc.).
• Strong coding skills with the ability to mentor and support team members in best practices and code quality.
• Experience consolidating codebases and managing complex technical debt.
• Ability to translate business challenges into actionable technical strategies.
• Excellent communicator who can lead through influence, not just authority.

Nice to Have

• Experience migrating or selecting modern CMS platforms.
• Familiarity with .NET, Node.js, React, and large-scale database refactoring.
• Exposure to AI/automation in support ops or DevOps workflows.
• Prior experience in a growth-stage or transformation-focused company.

Why This Role Matters
Our current systems have served us well, but they're showing their age — and they're limiting our ability to move fast, scale smoothly, and deliver great experiences. This role is central to building the technical foundation we need for the next 5–10 years.
What we offer

• 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

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