Product Manager at Headstart

Compensation

$240,000/yr

Setup: Remote, Hybrid
Location: New York, New York
Type: Full-time
Posted: Mar 12, 2026

Description

Headstart is seeking a Product Manager to lead product strategy and execution across complex enterprise engagements. The role involves shaping cross-client product strategy, ensuring AI product quality, and driving successful AI product delivery. The ideal candidate will have over 8 years of experience in B2B SaaS, enterprise AI, or applied AI/ML, with a strong background in platform operations and AI/ML systems.

Required Skills

Product Management
Enterprise AI
Applie AI/ML
Platform Operator
AI/ML Systems
Agent Architectures
Retrieval
Evaluation Pipelines
Observability
LLM Behavior
Model Choice
Latency
Cost
Safety
Writing Skills
Strategy Docs
Client Specs
Internal Frameworks

Additional Information

Required Previous Experiences: 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.
Preferred Qualifications: 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.