We work inside real enterprises ($100M+ ARR), shipping production AI systems that change how they operate. We're bootstrapped, cash-flow positive, and growing fast, and we're building our own platform to deliver truly agentic systems. Enterprise clients bring us messy, high-stakes problems, often with no clear picture of what the AI system should be.

Level: Reports to the Head of Engineering. Manage engineers up to senior, hold a high bar, and give direct, actionable feedback. Coach on execution and help strong engineers step up toward tech lead. Technical leadership.

Step into hard technical and client situations, like production regressions and unclear requirements, and make the call. Manage transitions on your team, plan ahead, and flag risks before they reach a client. Escalate conflicts across engagements to the Head of Engineering.

Interview, calibrate, close, and onboard current engineers against the bar the Head of Engineering sets. 5+ years in software engineering, deep enough to review designs and challenge the team's approach. Hands-on with Python. ~ Experience delivering software in real client environments.



~ Fluent with AI coding tools.

Bonus: management experience in a consulting, services, or forward deployed engineering organization, or experience taking a team or practice from zero to one. AI-first, human-accountable. Weekends are yours.

Technical screen (30 min): a short, real-world coding exercise with an engineer. # Technical interviews (2.5 hrs, two sessions): coding and systems design. Use AI tools in the coding interview, since it reflects how we work. # Case study (75 min): a live, scenario-based discussion covering staffing, feedback, technical review, and closing the loop. Base salary of $285,000 USD plus competitive equity ~401k with 4.5% employer match, and fully covered medical, dental, and vision premiums ~ Monthly wellness stipend, Citi Bike, and pre-tax commuter benefits ~12 weeks parental leave, with an optional 4-week ramp-up at 50% ~ Loft office in Soho with lunch and snacks ~ We're open to fully remote candidates in the US or Canada. #

📌 Principal Engineering Management Job (Ottawa)
🏢 Headstart
📍 Ottawa