At Headstart our mission is to bring companies into the age of intelligence and automate software development. We are the team behind the coding agent Friday and are building frontier applied AI technologies including agent orchestration, memory, and more.
We specialize in solving problems with the latest LLM capabilities that deliver measurable outcomes and breakthrough results for organizations in many different industries. As the technology continues to advance at an unprecedented rate, we provide companies with custom software solutions and a suite of tools to stay ahead of the intelligence curve.
About the teamWe are a lean, high-velocity team that ships breakthrough AI capabilities at startup speed. We work directly with our users, iterate rapidly, and measure success by the real-world impact we create for our clients. We believe that simplicity and product fundamentals are more important than ever in an AI driven world.
About the roleLead 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.
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.
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.
Note: Even if you don't meet all the requirements, we still encourage you to apply. This role offers extensive benefits, a base salary of $240,000 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, and 12 weeks parental leave with an optional 4-week ramp-up at a 50% schedule.
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.
Skills Required
- 8+ years of product management in B2B SaaS, enterprise AI, or applied AI/ML
- Comfortable working in AI/ML systems, including agent architectures and LLM behavior
- Exceptional writing skills for strategy docs and client specs
What We Do
Often, AI work is either research, internal workflows, or slide decks for clients. We're none of those. We're inside different businesses, working with different industries, constraints, and problems, building systems that are actually used in production. That variety is rare. Most engineers spend years in one domain. Our employees develop a kind of range that's hard to get anywhere else. We built our own agent, Friday, which means we're not just implementing other people's tools, we're pushing on what's actually possible and eating our own cooking. We're bootstrapped and cash-flow positive, which means no outside pressure. We are deliberate about culture; pay is transparent, weekends are yours, and we don't confuse long hours with good work. The people who thrive here are the ones who think like founders, who want to understand how businesses actually work, not just how the code works. If that's interesting to you, you'll grow faster here than almost anywhere else.
Why Work With Us
Every engagement at Headstart is a different industry, a different problem set, a different business to understand deeply. We build and deploy AI systems, including our own coding agent, Friday, for companies that need it done right, not just done fast. Fully-bootstrapped and cash-flow positive, so we control our destiny.
