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 01 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.
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 $240,000 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.
