Staff Product Manager

The role

You will lead product strategy and execution across enterprise engagements and shape cross-client product strategy. You will own AI product quality and turn delivery learnings into internal product IP.

What you will do

• Lead product strategy and execution across complex enterprise engagements
• Shape Headstart's cross-client product strategy
• Own AI product quality end-to-end
• Turn delivery learnings into internal product IP
• Navigate complex stakeholder dynamics and build executive relationships
• Lead 0 to 1 validation of AI products through rapid prototyping

Required qualifications

• 8+ years of product management in B2B SaaS, enterprise AI, or applied AI/ML
• Track record owning multi-phase, multi-stakeholder engagements from scoping through production
• 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 tradeoffs around model choice, latency, cost, and safety
• Strong judgment for AI product quality and readiness
• Exceptional writing skills

Benefits

• Base salary of $265,000 USD plus 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

About the company

Headstart aims to bring companies into the age of intelligence and automate software development. They are the team behind the coding agent Friday and build frontier applied AI technologies.