Senior Engineering Manager, Applied AI in Toronto

About The Company

Headstart is built for people who want to think like founders. We work inside real enterprises ($100M+ ARR), shipping production AI systems that change how they operate. Every engagement is a different industry, problem, and set of constraints. We're bootstrapped, cash-flow positive, and growing fast, and we're building our own platform to deliver truly agentic systems.

Why join us

Enterprise clients bring us messy, high-stakes problems, often with no clear picture of what the AI system should be. Our engineers work out what to build, build it, and run it in production. Most of the time, they're the experts in the room.

This role is part player, part coach, part staffing lead, part hiring engine. You'll start on a client engagement to learn the work and where engineers get stuck. Then you'll build and lead a team and help shape the company as we grow.

What You’ll Own

• Your team. Hold a high bar and grow each engineer through direct, actionable feedback. Develop senior engineers into tech leads. Give clear priorities and expectations without adding process before we understand the problem.
• 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. Raise trouble early, while it's cheap to fix.
• Closing the loop. Spot patterns across engagements and turn them into standing practice, reference implementations, and platform capabilities. Check that the next engagement is faster because of it.
• Staffing. Shape who works on which engagement, plan transitions ahead, and flag risks before they reach a client.
• Hiring. Run hiring for your team, from sourcing to onboarding. You define the bar.
• Partnerships. Work closely with product, client partners, and client stakeholders so each engagement lands.

Your background

• 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.
• Curious about agents, evals, and multi-agent systems, with a sense of where they're reliable and where a person needs to take the wheel.
• Fluent with AI coding tools. Depth matters more than prior title.
• Bonus: Management experience in a consulting, services, or forward deployed engineering organization.

How We Work

High trust, high agency, low ego. We push back when something isn't right and share what we learn, so good instincts spread fast. We are our first client. We built Friday, our coding agent, and Statum, our knowledge infrastructure, and we run them on ourselves. AI-first, human-accountable. Agents write nearly all our client code. Every output is reviewed, and the person is accountable. Partners, not a vendor. You're in the room when hard calls get made, and you're expected to have a point of view. Breadth that compounds. You'll see more industries and problems in a year than most people see in a career. Weekends are yours. Pay is transparent, and we don't confuse long hours with good work.

What To Expect

• Initial screen (30 min): with our recruiting partner.
• Technical screen (30 min): a short, real-world coding exercise with an engineer.
• Hiring manager interview (45 min): behavioral and past work.
• 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. No prep needed.

What we offer

• 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.

Compensation Range: $300K