About this Staff Engineer, Applied AI role at Headstart
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
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.
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.
