Hybrid Head of Engineering

at SkyWatch

• Job title: Head of Engineering
• Job type: Full Time
• Experience level: Lead
• Salary: Not specified
• Degree requirement: Bachelor's Degree
• Tech skills: Cloud
• Location requirements: Hybrid, Kitchener, Canada

About the role

• Lead the engineering team at SkyWatch and drive modern software development practices. Champion AI-assisted tooling and manage delivery and productivity to make impactful contributions.

Responsibilities

• Own people leadership for the full engineering team: 1:1s, career development, performance management, hiring, and team health. Build a culture of ownership, customer empathy, and technical craftsmanship. Manage a team that includes experienced senior engineers with strong technical opinions.
• Design and evolve our engineering processes, tooling, and quality standards. Build internal scaffolding, templates, and guardrails that make it easy to do the right thing and hard to do the wrong thing. Invest in automated quality controls that catch problems before they reach anyone downstream. You care about cycle time, developer experience, and the gap between intent and production.
• Champion modern tooling. We believe AI-assisted development is a genuine multiplier for small teams, not a novelty. You should already be using these tools effectively and have a point of view on how to integrate them into real engineering workflows. You will lead by example and help the team adopt new practices at a pace that builds confidence rather than resistance.
• Own the flow of work from intent to production. Make sure the team is working on the right things in the right order. Unblock people when they are stuck. Work with product leadership to ensure decision gates keep work aligned with customer needs without becoming bottlenecks.
• Invest in the systems that make the team more productive over time: CI/CD pipelines, testing infrastructure, service documentation, onboarding tooling, and security scanning. The goal is a codebase and development environment that any engineer can navigate and contribute to quickly.

Requirements

• Hands-on technical depth. You can build, not just manage. You write code, review architecture, and earn the respect of strong engineers through your craft.
• Experience leading engineering teams through meaningful process or tooling changes — not just maintaining the status quo.
• Real fluency with AI-assisted development. You are already using these tools productively, not just evaluating them.
• People leadership skills that go beyond scheduling stand-ups. You can coach, give hard feedback, navigate strong personalities, and build trust.
• Experience with cloud-native, serverless architectures.
• A bias toward building internal tooling and developer experience as a force multiplier for the team.

Benefits

• Competitive salary
• Flexible working hours
• Professional development budget
• Home office setup allowance
• Global team events