Staff Engineer, Applied AI

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 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

• 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

• 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 challengers, and knowing when to lean on deterministic solutions

• Enjoys a fast-paced 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

What to expect

1. Initial screen (30 min): a conversation with our recruiting partner about your background, what you're looking for, and how we work.

2. Technical screen (30 min): a short, real-world coding exercise with an engineer from our team.

3. Hiring manager interview (45 min): behavioral and past work with a member of the team

4. 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.

5. Project deep dive (1 hr): for Staff candidates only. A conversation with a fellow engineer about something significant you've built.

What we offer

This role offers extensive benefits, including:

• a base salary of $265,000 USD

• competitive equity compensation

• 401k with 4.5% employer match

• fully covered medical, dental, and vision premiums

• monthly wellness stipend

• Citi Bike + pre-tax commuter benefits

• 12 weeks parental leave with an optional 4-week ramp-up at a 50% schedule.

If you’re NYC based — we have a loft office in Soho and provide lunch and snacks

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.

Note: Even if you don't meet all the requirements, we still encourage you to apply.