Senior Engineering Manager, Applied AI
Headstart — Toronto, Ontario
Full-Time
Oct 3, 2026
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About This Position
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 …
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