Staff Engineer, Applied AI

About the role

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

WHY JOIN US

Engineers who thrive at Headstart are builders who want to understand both how businesses and code works. 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

- Operate as technical lead on complex and ambiguous client engagements end-to-end, from ideation and discovery through to production

- Be the technical authority in sales and scoping conversations: lead with clear recommendations, drive technical strategy forward, and keep the conversation focused on accomplishing engagement goals

- Shape client strategy by reframing problems, influencing priorities, and defining what the right path forward looks like

- Build 0 -> 1 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 by identifying and delivering high leverage investments across our tooling and infrastructure

- Grow the engineers around you and act as player-coach to 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

- Have owned client relationships at the executive level: running discovery, navigating difficult conversations, and earning trust quickly

- Communicates with structure: you answer the question that was asked, get to the point quickly, and can go deeper when someone asks without losing the thread

- Been the technical authority in rooms with executives and clients and have shaped what got built, not just built what you were told

- Have designed and shipped agentic systems to solve complex user challenges, and know when to lean on deterministic solutions

- Enjoys a fast-paced, transparent, and collaborative environment

- 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