Location: Scarborough, Ontario
Seeking a Director of Technology with a strategic acumen of an executive and the technical skills of a Principal Architect.
In this role you will be the final word on our technical stack, a mentor in the trenches, and a hands-on contributor to our most complex software challenges. You will lead our technology team by example, ensuring our tools are world-class, and our innovation is driven by the latest in AI and automation.
What Sets This Role Apart:
- Lead from the Front: Spend significant time in the codebase, conducting deep-dive code reviews and prototyping core architectural components.
- AI-Driven Velocity: Act as the chief architect of our internal AI transformation. You will lead the team in integrating Generative AI and LLMs into our development lifecycle—automating repetitive tasks and optimizing CI/CD.
- Modernize the Stack: Take ownership of our software tools, ensuring we are utilizing the best-in-class frameworks and AI-augmented automation.
- Solve the Impossible: Act as the ultimate escalation point for the most difficult technical bottlenecks and performance issues.
Core Responsibilities:
- Hands-on Architecture: Design and implement core services that define our platform’s scalability.
- Collaborative Innovation: Partner with the team to foster a fail-fast culture, brainstorming alongside devs to build next-gen features.
- Automated Excellence: Oversee the implementation of Autonomous Agents within our DevOps pipeline to automate testing, security, and scaling.
- Tooling & DX: Audit and evolve our internal software tools and CI/CD pipelines to ensure a friction-free workflow.
- High-Performance Culture: Recruit and retain A-player engineers by speaking their language and earning their technical respect through shared execution.
Must Have Skills:
Requirements:
- Engineering Pedigree: 12+ years of experience in software engineering, with at least 5 years in a formal leadership role (VP or Director). We are looking for someone who grew up in code and still loves it.
- The Player-Coach Capability: You must be able to pass a high-level system design and live coding assessment. You should be comfortable jumping into a repo and identifying a performance bottleneck or a security flaw.
- AI Proficiency (2026 Standard): Proven experience implementing Agentic AI or LLM-based automation into production workflows. You should be familiar with the modern AI stack (e.g., LangChain, vector databases, or custom agent orchestration).
- Infrastructure Mastery: Expert-level understanding of cloud-native architecture (AWS or Azure), Kubernetes, and Infrastructure as Code (Terraform/Pulumi).
- Modern Language Fluency: Professional-grade experience in at least two of the following: Go, Rust, Node.js, or Python.
- Strategic Communication: Ability to translate complex technical trade-offs (e.g., build vs. buy or technical debt vs. feature velocity) into clear business ROI for the CEO and Board.
