Staff Product Manager

Role Overview

Lead product strategy and execution across complex enterprise engagements, shape Headstart's cross-client product strategy, and own AI product quality end-to-end.

What You Will Do

Lead 0→1 validation of AI products through rapid prototyping and fast iteration, advise senior client leaders on AI operating models, and translate technical tradeoffs into business outcomes.

Why It Might Be a Fit

8+ years of product management experience in B2B SaaS, enterprise AI, or applied AI/ML, with a track record owning multi-phase, multi-stakeholder engagements from scoping through production.

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
• 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
• 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

Benefits

• Base salary of $200,000 USD
• 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
• 12 weeks parental leave with an optional 4-week ramp-up at a 50% schedule