Staff Product Manager

At Headstart our mission is to bring companies into the age of intelligence and automate software development. We are the team behind the coding agent Friday and are building frontier applied AI technologies including agent orchestration, memory, and more.

We specialize in solving problems with the latest LLM capabilities that deliver measurable outcomes and breakthrough results for organizations in many different industries. As the technology continues to advance at an unprecedented rate, we provide companies with custom software solutions and a suite of tools to stay ahead of the intelligence curve.

We are a lean, high-velocity team that ships breakthrough AI capabilities at startup speed. We work directly with our users, iterate rapidly, and measure success by the real-world impact we create for our clients. We believe that simplicity and product fundamentals are more important than ever in an AI driven world.

• Lead product strategy and execution across complex enterprise engagements, from discovery through multi-SOW roadmaps and long-term platform vision.

• Shape Headstart's cross-client product strategy by identifying patterns, building reusable frameworks, and scaling AI product delivery.

• Own AI product quality end-to-end, defining success metrics, evaluation frameworks, guardrails, and production-readiness standards alongside engineering and leadership.

• Turn delivery learnings into internal product IP, including telemetry standards, analytics boilerplates, and agentic curriculum.

• Navigate complex stakeholder dynamics, build executive relationships, drive SOW expansion, and push back when it improves outcomes.

• Lead 0→1 validation of AI products through rapid prototyping and fast iteration, advising senior client leaders on AI operating models and translating technical tradeoffs into business outcomes.

• 8+ years of product management in B2B SaaS, enterprise AI, or applied AI/ML, with a track record owning multi-phase, multi-stakeholder engagements from scoping through production.

• Platform-level operator who builds frameworks, standards, and reusable IP that outlast individual engagements.

• Comfortable working in AI/ML systems, including agent architectures, retrieval, evaluation pipelines, observability, LLM behavior, and the tradeoffs around model choice, latency, cost, and safety.

• Strong judgment for AI product quality and readiness, with a track record defining success metrics and measurable business outcomes, not just shipping features.

• Exceptional writing skills, producing clear, durable strategy docs, client specs, and internal frameworks.

• Comfortable advising senior client leaders on AI operating models, investment priorities, and change management, translating technical complexity into business decisions.

Note: Even if you don't meet all the requirements, we still encourage you to apply. This role offers extensive benefits, a base salary of $265,000 USD plus competitive equity compensation, 401k with employer match, fully covered medical, dental, and vision premiums, monthly wellness stipend, free lunch everyday in our NYC office, Citi Bike + pre-tax commuter benefits, and 12 weeks parental leave with an optional 4-week ramp-up at a 50% schedule.

While this position is listed as hybrid in NYC or Toronto, we are open to considering fully remote candidates based in the US or Canada for the right fit.