Senior, Applied AI Engineer

Headstart•New York, NY

5d•$225,000 - $225,000•Hybrid

About The Position

Headstart 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. The engineers who thrive at Headstart are the ones who want to understand how businesses work, not just how 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. We have a sun-drenched loft office in NYC and a remote-friendly culture to support those outside of NYC. Own client engagements end-to-end, from technical discovery and scoping through to production. Work directly with enterprise clients, translating ambiguous business problems into concrete technical scope. Ship production AI systems across multiple domains and stacks: agents, LLM workflows, document processing, and the infrastructure that makes them reliable. Contribute to Friday and the Headstart Platform via patterns, skills, and infrastructure that compound across every engagement. Raise the bar for the engineers around you through code review, pairing, and shared standards.

Requirements

5+ years of engineering experience with a track record of owning systems end-to-end
Comfortable in client-facing situations, running discovery, earning trust quickly, and shaping what gets built
Your instincts and standards are contagious and teammates adopt them naturally
You use AI tools constantly, creatively, and with good judgment about when not to
Proven full-stack depth: backend services (Python), datastores (SQL/NoSQL), optionally React/Next.js
Experience designing distributed systems, APIs, data pipelines, or developer productivity infrastructure at scale

Nice To Haves

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

Responsibilities

Own client engagements end-to-end, from technical discovery and scoping through to production
Work directly with enterprise clients, translating ambiguous business problems into concrete technical scope
Ship production AI systems across multiple domains and stacks: agents, LLM workflows, document processing, and the infrastructure that makes them reliable
Contribute to Friday and the Headstart Platform via patterns, skills, and infrastructure that compound across every engagement
Raise the bar for the engineers around you through code review, pairing, and shared standards