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
- 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.
- Project deep dive (1 hr): for Staff candidates only. A conversation with a fellow engineer about something significant you've built.
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 $265,000 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.
