Headstart
Staff Engineer, Applied AI
New York, NY, Remote. Posted 9 months ago
The role
You will act as a technical lead on complex client engagements from ideation to production. You will shape client strategy, build systems rapidly, and contribute to the Headstart Platform.
What you will do
- Operate as technical lead on complex and ambiguous client engagements end-to-end
- Be the technical authority in sales and scoping conversations
- Shape client strategy by reframing problems and influencing priorities
- Build 0 -> 1 rapidly while ensuring long-term reliability, maintainability, and security
- Balance multiple concurrent engagements across different technical stacks and business domains
- Contribute to the Headstart Platform by delivering high leverage investments
- Grow the engineers around you and act as player-coach
Required qualifications
- 7+ years of professional software engineering experience
- Owned client relationships at the executive level
- Communicates with structure
- Been the technical authority in rooms with executives and clients
- Designed and shipped agentic systems to solve complex user challenges
- Full-stack depth: backend services (Python), datastores, React/Next.js
- Experience designing distributed systems, APIs, data pipelines, or developer productivity infrastructure at scale
Nice to have
- ML
- Founding engineer or startup early hire with history building production products from scratch
Benefits
- 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
- lunch and snacks if NYC based
Before you apply
- Initial screen (30 min)
- Technical screen (30 min) with a real-world coding exercise
- Hiring manager interview (45 min)
- Technical interviews (2.5 hrs total) including coding and systems design
- Project deep dive (1 hr) for Staff candidates
About the company
Headstart builds production AI systems for enterprises with $100M+ ARR. They are a bootstrapped, cash-flow positive company building their own platform and coding agent.