---
title: 'Engineering Manager, Applied AI at Headstart'
canonical: 'https://feeny.ai/job/engineering-manager-applied-ai-headstart-new-york-21phjhf8vbns'
type: 'job'
last_seen: '2026-10-19'
---

# Engineering Manager, Applied AI at Headstart

- **Company:** Headstart
- **Location:** New York, NY
- **Compensation:** $285k
- **Employment:** full-time
- **Work type:** hybrid
- **Posted:** 2026-09-29
- **Last confirmed live:** 2026-10-19
- **Apply:** https://jobs.ashbyhq.com/headstart/c66f9773-f82c-48a7-8c57-09c47b4324ba

## 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, problem, and set of constraints. We're bootstrapped, cash-flow positive, and growing fast, and we're building our own platform to deliver truly agentic systems.

## Why join us

Enterprise clients bring us messy, high-stakes problems, often with no clear picture of what the AI system should be. Our engineers work out what to build, build it, and run it in production. Most of the time, they're the experts in the room. This role is part player, part coach, part staffing partner. Most of your time stays on a client engagement, hands-on, close to the work and to where engineers get stuck. You'll manage a group of engineers across a few engagements and grow with the team as we do. Level: Reports to the Head of Engineering. You run a team inside our system: you apply the bar, keep your engineers growing, and stay close to the work.

## What you'll own

- Your engineers. Manage engineers up to senior, hold a high bar, and give direct, actionable feedback. Coach on execution and help strong engineers step up toward tech lead.
- Technical leadership. Review architecture, agent, prompt, and eval design on your engagements. Step into hard technical and client situations, like production regressions and unclear requirements, and make the call. Raise trouble early, while it's cheap to fix.
- Engagement delivery. Run the engagement-level relationship with clients and their stakeholders, alongside product and client partners, so each engagement lands.
- Staffing. Manage transitions on your team, plan ahead, and flag risks before they reach a client. Escalate conflicts across engagements to the Head of Engineering.
- Hiring. Interview, calibrate, close, and onboard new engineers against the bar the Head of Engineering sets.
- Practice. Follow the team's practices and tell us what isn't working. Bring patterns you see to the wider team so they can become standing practice, and make sure your engineers use what exists.

## Your background

- 3+ years managing engineers, with real experience giving feedback and developing people.
- 5+ years in software engineering, deep enough to review designs and challenge the team's approach. Hands-on with Python.
- Experience delivering software in real client environments.
- Curious about agents, evals, and multi-agent systems, with a sense of where they're reliable and where a person needs to take the wheel. Fluent with AI coding tools. Depth matters more than prior title.

Bonus: management experience in a consulting, services, or forward deployed engineering organization, or experience taking a team or practice from zero to one.

## How we work

High trust, high agency, low ego. We push back when something isn't right and share what we learn, so good instincts spread fast.

- We are our first client. We built Friday, our coding agent, and Statum, our knowledge infrastructure, and we run them on ourselves.
- AI-first, human-accountable. Agents write nearly all our client code. Every output is reviewed, and the person is accountable.
- Partners, not a vendor. You're in the room when hard calls get made, and you're expected to have a point of view.
- Breadth that compounds. You'll see more industries and problems in a year than most people see in a career.
- Weekends are yours. Pay is transparent, and we don't confuse long hours with good work.

What to expect

- Initial screen (30 min): with our recruiting partner.
- Technical screen (30 min): a short, real-world coding exercise with an engineer.
- Hiring manager interview (45 min): behavioral and past work.
- Technical interviews (2.5 hrs, two sessions): coding and systems design. Use AI tools in the coding interview, since it reflects how we work.
- Case study (75 min): a live, scenario-based discussion covering staffing, feedback, technical review, and closing the loop. No prep needed.

## What we offer

- Base salary of $285,000 USD plus competitive equity
- 401k with 4.5% employer match, and fully covered medical, dental, and vision premiums
- Monthly wellness stipend, Citi Bike, and pre-tax commuter benefits
- 12 weeks parental leave, with an optional 4-week ramp-up at 50%
- Loft office in Soho with lunch and snacks
- Hybrid in NYC. We're open to fully remote candidates in the US or Canada.

## 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

- [Senior Engineering Manager, Applied AI](https://feeny.ai/job/senior-engineering-manager-applied-ai-headstart-new-york-qxrwdehcpbam) — New York, NY
- [Staff Product Manager](https://feeny.ai/job/staff-product-manager-headstart-new-york-xs9wg7teftak) — New York, NY
- [Staff Engineer, Applied AI](https://feeny.ai/job/staff-engineer-applied-ai-headstart-new-york-38gmjjte70sc) — New York, NY
- [Engineering Manager, Applied AI](https://feeny.ai/job/engineering-manager-applied-ai-mercor-san-francisco-ve8jgbxp923w) — San Francisco, CA