Headstart

Staff Product Manager

Headstart

full-time

Posted on:

Location Type: Hybrid

Location: New York City • New York • United States

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Salary

💰 $240,000 per year

Job Level

Lead

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.

Requirements

  • 8+ years of product management in B2B SaaS, enterprise AI, or applied AI/ML
  • 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.
Benefits
  • 401k match
  • Competitive equity compensation
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
product managementB2B SaaSenterprise AIapplied AImachine learningAI product qualitysuccess metricsevaluation frameworksrapid prototypingAI operating models
Soft Skills
leadershipcommunicationjudgmentrelationship buildingchange managementwriting skillsstakeholder managementstrategic thinkingproblem solvingcollaboration