---
title: 'Staff, Applied AI Engineer at Headstart'
canonical: 'https://feeny.ai/job/staff-applied-ai-engineer-headstart-new-york-38gmjjte70sc'
type: 'job'
last_seen: '2026-09-07'
---

# Staff, Applied AI Engineer at Headstart

- **Company:** Headstart
- **Location:** New York, NY
- **Compensation:** $265k
- **Employment:** full-time
- **Work type:** hybrid
- **Posted:** 2026-01-23
- **Last confirmed live:** 2026-09-07
- **Apply:** https://jobs.ashbyhq.com/headstart/a0f891b6-b05c-4724-90a3-601f5040df87

## Job description

## ABOUT THE COMPANY

Headstart https://www.headstart.nyc/ is built for people who want to think like founders. We work inside real enterprises ($100M+ ARR) shipping production AI systems that change how they operate. Every engagement is a different industry, a different problem, and a different set of constraints. You leave each one knowing that business deeply.

We've built our own agent Friday, which powers the majority of how we deliver. We're bootstrapped, cash-flow positive, and growing fast.

## WHY JOIN US

The engineers who thrive at Headstart are the ones who want to understand how businesses work, not just how code works. We work inside real enterprises, shipping production AI systems that change how they operate. We take the work seriously and the culture deliberately. Pay is transparent, weekends are yours, and we don't confuse long hours with good work.

## ABOUT THE ROLE

- Lead and own multiple client engagements end-to-end, from ideation and technical discovery through to production
- Prototype rapidly while ensuring long-term reliability, maintainability, and security
- Balance multiple concurrent engagements, context-switching between different technical stacks and business domains
- Contribute to the Headstart Platform roadmap by identifying and delivering the highest-leverage investments across our tooling and infrastructure
- Shape client strategy by reframing problems, influencing priorities, and defining what the right path forward looks like
- Be the technical authority in sales and scoping conversations
- Grow the engineers around you and raise the floor of every project you work on

## YOUR BACKGROUND

- 7+ years of professional software engineering experience with a track record of owning complex, high-stakes systems end-to-end
- Been the technical authority in rooms with executives and clients and have shaped what got built, not just built what you were told
- Experience creatively applying AI in the development lifecycle, and knowing when not to
- Enjoys a fast-paced and collaborative environment
- Have owned client relationships at the executive level: running discovery, navigating difficult conversations, and earning trust quickly
- Proven full-stack depth: backend services (Python), datastores, React/Next.js, optionally ML
- Experience designing distributed systems, APIs, data pipelines, or developer productivity infrastructure at scale
- Bonus if you’ve been a founding engineer or startup early hire, with history building production products from scratch
- Bonus if you’re NYC based — we have a loft office in Soho and provide lunch and snacks

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)

## Other roles at Headstart

- [Staff Product Manager](https://feeny.ai/job/staff-product-manager-headstart-new-york-xs9wg7teftak) — New York, NY