Staff Product Manager
New
H
HeadstartApplied AI
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.Full-TimeStaff
Salary$240K
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Job Details
- Experience
- 8+ years
- Required Skills
- Machine LearningProduct ManagementLLM
Requirements
- 8+ years of product management experience in B2B SaaS, enterprise AI, or applied AI/ML.
- Track record owning multi-phase, multi-stakeholder engagements from scoping through production.
- Experience building platform-level frameworks, standards, and reusable IP.
- Deep understanding of AI/ML systems including agent architectures, retrieval, evaluation pipelines, observability, and LLM behavior.
- Knowledge of tradeoffs around model choice, latency, cost, and safety.
- Ability to define success metrics and measurable business outcomes for AI products.
- Exceptional writing skills for strategy documentation and client specifications.
- Experience advising senior leadership on AI operating models, investment priorities, and change management.
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.
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