Head of Engineering

SkyWatch•Kitchener, ON

80d

About The Position

We are looking for a Head of Engineering to lead our engineering team through a period of meaningful evolution in how we build software. This is not a management-only position. You are a technical leader first — someone who earns credibility by building, not just directing. You will own engineering operations, delivery, people leadership, and the developer experience. You will work closely with the CTO, who focuses on technology strategy and customer-facing work, and the CPO, who owns the product roadmap. Your job is to make the team excellent at turning product intent into production software, quickly and reliably. The right person for this role has strong opinions about modern engineering practices, is already using AI-assisted development tools productively, and is excited about building the systems and culture that let a small team punch well above its weight.

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.

Nice To Haves

Experience in geospatial, Earth observation, or data platform domains.
Familiarity with government compliance and certification requirements.
Experience transitioning engineering work from external vendors to in-house teams.
Background building internal platforms, developer tooling, or engineering enablement Systems.