About the Role

We’re building the future of tenant risk underwriting—and we’re doing it profitably. SingleKey is the leading tenant screening and rent guarantee provider across Canada. We power leasing decisions for both independent landlords and multifamily operators, giving homeowners smarter, faster tools to screen, lease, and guarantee tenants with confidence.

We’re looking for a Head of Engineering to be SingleKey’s senior-most technical leader — the person who will keep our architecture coherent, our systems secure, and our engineering team organized and focused. You’ll set and enforce technical standards, make the big architectural calls, and ensure we’re ready for the scale and compliance demands of serving Canada’s largest housing providers.

This is a hands-on leadership role. You’ll spend time reviewing critical code, guiding architectural decisions, and mentoring engineers, while also shaping processes, managing people, and building the team for future growth. You will work directly with the CEO and Head of Product to scale our infrastructure and develop the foundational data models that will power our next generation of AI-driven risk engine.

Responsibilities

Own Technical Architecture & Standards

• Lead architectural decisions across the stack to ensure solutions are scalable, maintainable, and compliant with regulatory requirements.
• Keep our systems coherent as we evolve toward enterprise-grade performance and security.

Be the Senior Technical Authority

• Serve as the final escalation point for complex technical decisions.
• Provide clear technical direction to the engineering team and ensure all teams are aligned.

Organize & Elevate the Team

• Implement and refine engineering processes to improve delivery, quality, and cross-team collaboration.
• Ensure the engineering roadmap is realistic, prioritized, and consistently delivered.

Scale the Team for Growth

• Partner with leadership to define the engineering org structure needed for the next 12–24 months.
• Lead hiring for key technical roles, both onshore and offshore, ensuring new talent strengthens our architecture, compliance, and delivery capabilities.
• Develop career paths and growth plans for existing engineers to prepare them for expanded responsibilities as the company scales.

Hands-On Leadership

• Conduct in-depth code reviews for high-impact changes.
• Contribute directly to key architectural components and critical projects when needed.
• Mentor engineers through design sessions, pair programming, and technical coaching.

Bridge Between Business & Engineering

• Partner with Product, Design, and Operations to ensure feasibility, security, and delivery timelines are realistic and aligned with company priorities.

Grow Talent & Leadership

• Mentor and develop the current engineering manager and senior engineers, preparing them to lead teams independently as we scale.

Requirements

• 8+ years in software engineering, including significant experience as the technical decision-maker for complex SaaS systems.
• Proven experience leading engineering teams, establishing development processes, and scaling teams through thoughtful hiring.
• Deep architectural expertise in modern backend stacks (Python, Node.js, or similar) and cloud infrastructure (AWS/GCP).
• Strong understanding of multi-tenant architectures, data security, and regulatory compliance (SOC 2, ISO 27001, etc.).
• Track record of balancing high-level strategy with hands-on technical contributions.
• Excellent communication skills and the ability to align technical execution with business goals.
• Experience recruiting and managing both onshore and offshore engineering talent.
• Able to lead implementation of GenAI and ML to enhance risk models, automate processes, and deliver a smarter product.

What We Offer

Meaningful Ownership

• Receive a meaningful equity stake in a profitable, fast-growing company where your contributions directly impact the bottom line.

A High-Performing, Low-Ego Team

• Join a focused and mission-driven group that values direct feedback, moves quickly, and is passionate about solving real-world problems for our customers.

Technical Authority & Impact

• As the top technical leader, you’ll set the standards, make the architectural decisions, and shape the team that will power our next stage of growth.

Build for Scale

• Lead the evolution of our systems to handle a 10x increase in transaction volume, enterprise-grade security, and full regulatory compliance.

Hybrid & Flexible Work

• Based out of our Toronto hub, with 2–3 days per week in-office for key collaboration and leadership meetings.

Benefits & Tools

• Comprehensive health and dental coverage, parental leave, flexible vacation policy, professional development budget, and the best tools for the job.

This is a rare opportunity to take full ownership of a high-impact SaaS platform, lead and grow a talented engineering team, and set the technical foundation for the next stage of our growth.

Ready to lead and build? Apply now.