---
title: 'Staff Product Manager at Headstart'
canonical: 'https://feeny.ai/job/staff-product-manager-headstart-new-york-xs9wg7teftak'
type: 'job'
last_seen: '2026-09-07'
---

# Staff Product Manager at Headstart

- **Company:** Headstart
- **Location:** New York, NY
- **Compensation:** $265k
- **Employment:** full-time
- **Work type:** hybrid
- **Posted:** 2026-03-12
- **Last confirmed live:** 2026-09-07
- **Apply:** https://jobs.ashbyhq.com/headstart/5890a597-f72d-4968-9a54-397bff0c0c9b

## Job description

## ABOUT THE COMPANY

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 TEAM

We 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 ROLE

- 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.

## YOUR BACKGROUND

- 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 $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, 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.

## About Headstart

## Company Overview
- **One-liner**: Headstart partners with digitally native businesses to ship production AI systems that work, operating across different industries and building custom solutions, including their own coding agent, Friday.
- **Entity Type**: Private (Bootstrapped)
- **Headquarters**: New York, New York, USA
- **Founded**: 2022
- **Founders**: Nicole Hedley (Co-Founder & CEO), Chris Hedley (Co-Founder)

## Core Business
- **Primary industry/industries**: Software Development, Applied AI, AI Consulting
- **Target customers**: B2B; digitally native businesses and real enterprises ($100M+ ARR)
- **Mission or purpose statement**: To bring companies into the age of intelligence and automate software development.

## Products & Services
- **Friday (AI Coding Agent)**: Headstart's own proprietary coding agent that powers the majority of how they deliver client work. It represents a core internal tool and product differentiator.
- **Custom AI Production Systems**: End-to-end custom software solutions for clients, spanning ideation, technical discovery, architecture, deployment, and production. Each engagement targets a different industry, problem set, and set of constraints.
- **Headstart Platform**: Internal tooling and infrastructure investments that scale AI product delivery across client engagements, including reusable frameworks, telemetry standards, and agent orchestration capabilities.

## Market Standing
- **Valuation/Market Cap**: Not publicly available (bootstrapped)
- **Key Metric**: Bootstrapped and cash-flow positive; 22 total employees (as of July 2026)
- **Notable Investors/Partners**: No external investors (bootstrapped). Clients are real enterprises with $100M+ ARR.
- **Growth Signals**: Growing fast (5 active job postings as of July 2026); Quarterly job posting growth of +25.0%; LinkedIn follower count of 722 (monthly growth of +4.3%); expanding presence with offices in NYC and Spain.

## Competitive Advantages
- **Bootstrapped & Cash-Flow Positive**: No outside pressure from investors; full control over their destiny and culture.
- **Production-First AI**: Unlike many firms focused on research or internal workflows, Headstart builds and ships AI systems that are *actually used in production*.
- **Proprietary Agent (Friday)**: They aren't just implementing other people's tools; they built their own agent, pushing the frontier of what's possible and "eating their own cooking."
- **Cross-Industry Variety**: Engineers gain exposure to a wide range of industries, problems, and constraints, developing a breadth of experience rare in the industry.
- **Founder-Minded Culture**: The company deliberately hires and cultivates people who "think like founders" and want to understand how businesses work, not just how code works.

## Strategic Focus
- **Current priorities**: Scaling their delivery capacity through hiring (Staff and Senior Software Engineers, Staff Product Managers); deepening the capabilities of their proprietary agent (Friday) and the Headstart Platform; expanding client engagements across new industries and geographies (NYC, Toronto, Spain).
- **Direction for growth**: Moving from individual client engagements to a platform-level product strategy, building reusable IP, frameworks, and standards that can scale across multiple clients and industries.

## Why Work Here
- **Culture highlights**: Deliberate and transparent culture. Pay is transparent, weekends are yours, and they don't confuse long hours with good work. The company values founder-minded thinking and real-world impact over just shipping features.
- **Remote/hybrid/office policy**: Hybrid. They have a loft office in Soho, NYC, and are also open to fully remote candidates based in the US or Canada for the right fit. Typical time on-site is hybrid (employees work from physical offices but not daily).
- **Notable perks or engineering culture**: Free lunch every day in the NYC office; fully covered medical, dental, and vision premiums; 401k with employer match; monthly wellness stipend; Citi Bike + pre-tax commuter benefits; 12 weeks parental leave with an optional 4-week ramp-up at a 50% schedule. Base salary for Staff-level roles is $240,000 USD plus competitive equity compensation. The engineering culture emphasizes rapid prototyping, long-term reliability, and direct client interaction.

## Sources
1. [Built In NYC - Headstart AI Company Profile](https://www.builtinnyc.com/company/headstart-ai)
2. [Built In - Staff Software Engineer Job Posting](https://builtin.com/job/staff-software-engineer/7932081)
3. [Built In - Staff Product Manager Job Posting](https://builtin.com/job/staff-product-manager/8733930)
4. [LinkedIn - Headstart AI Company Page](https://www.linkedin.com/company/headstartai)
5. [Headstart - Careers Page (Ashby)](https://jobs.ashbyhq.com/Headstart)

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