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.
Why join usThe 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 for those outside of NYC.
About the roleOwn 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
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
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 $200,000 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.
Skills Required
- 5+ years of professional software engineering experience
- Proven track record owning full-stack systems
- Strong interest in leveraging AI in the development lifecycle
- Experience designing distributed systems, APIs, or data pipelines
What We Do
Often, AI work is either research, internal workflows, or slide decks for clients. We're none of those. We're inside different businesses, working with different industries, constraints, and problems, building systems that are actually used in production. That variety is rare. Most engineers spend years in one domain. Our employees develop a kind of range that's hard to get anywhere else. We built our own agent, Friday, which means we're not just implementing other people's tools, we're pushing on what's actually possible and eating our own cooking. We're bootstrapped and cash-flow positive, which means no outside pressure. We are deliberate about culture; pay is transparent, weekends are yours, and we don't confuse long hours with good work. The people who thrive here are the ones who think like founders, who want to understand how businesses actually work, not just how the code works. If that's interesting to you, you'll grow faster here than almost anywhere else.
Why Work With Us
Every engagement at Headstart is a different industry, a different problem set, a different business to understand deeply. We build and deploy AI systems, including our own coding agent, Friday, for companies that need it done right, not just done fast. Fully-bootstrapped and cash-flow positive, so we control our destiny.
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