We work inside real enterprises ($100M+ ARR), shipping production AI systems that change how they operate. We're bootstrapped, cash-flow positive, and growing rapid, 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.

Then you'll build and lead a team and help shape the company as we grow. Hold a high bar and grow each engineer through direct, actionable feedback. Develop senior engineers into tech leads. Technical leadership.

Review architecture, agent, prompt, and eval design. Step into the hardest technical and client situations, like production regressions and unclear requirements, and make the call. Spot patterns across engagements and turn them into standing practice, reference implementations, and platform capabilities.

Shape who works on which engagement, plan transitions ahead, and flag risks before they reach a client. 4+ years managing engineers, including senior and staff, with real experience hiring and developing them. ~8+ 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 and taking something from zero to one, whether a team, a practice, or a hiring process. ~ Fluent with AI coding tools.

Bonus: Management experience in a consulting, services, or forward deployed engineering organization. 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 $300,000 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 ~ Hybrid in NYC, and fully remote in the rest of the US and Canada. #

📌 Senior Engineering Manager, Applied AI (Toronto)
🏢 Headstart
📍 Toronto