Senior, Applied AI Engineer

About The Company

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 us

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.

About The Role

• 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
  
  

Your background

• 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
  
  

What To Expect

• Initial screen (30 min): a conversation with our recruiting partner about your background, what you're looking for, and how we work.
• Technical screen (30 min): a short, real-world coding exercise with an engineer from our team.
• Hiring manager interview (45 min): behavioral and past work with a member of the team
• Technical interviews (2.5 hrs total, split across two sessions): a coding interview and a systems design interview. You're encouraged to use AI tools in the coding interview; it reflects how we work day to day.
  
  

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 $225,000 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.

Compensation Range: $225K

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