Staff Product Manager

Headstart•New York, NY

3d•$240,000•Hybrid

About The Position

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.

Requirements

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.

Responsibilities

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.