Staff Product Manager

About the Role

• 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.

Your Background

• 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.

Pay and benefits

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.