Senior Engineering Manager, Applied AI
Role Overview
The role combines engineering management, hands-on technical leadership, staffing, and hiring.
The manager starts on a client engagement, then builds and leads a team and contributes to company growth.
Key Skills for This Role
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About Headstart
Headstart delivers production AI systems for enterprise clients and is building a platform for agentic systems.
Client engagements involve varied industries, high-stakes problems, and evolving requirements.
Role overview
The role combines engineering management, hands-on technical leadership, staffing, and hiring.
The manager starts on a client engagement, then builds and leads a team and contributes to company growth.
What you will own
- Develop engineers through direct feedback, clear priorities, and expectations; help senior engineers become tech leads.
- Review architecture, agent, prompt, and evaluation designs; handle difficult technical and client situations.
- Spot patterns across engagements and create practices, reference implementations, and platform capabilities.
- Plan staffing and transitions, and identify risks before they reach clients.
- Lead team hiring from sourcing through onboarding and define hiring standards.
- Partner with product, client partners, and client stakeholders to deliver successful engagements.
Background
- 4+ years managing engineers, including senior and staff engineers, with hiring and development experience.
- 8+ years in software engineering and hands-on Python experience.
- Experience delivering software in client environments and taking a team, practice, or hiring process from zero to one.
- Curiosity about agents, evaluations, and multi-agent systems, and fluency with AI coding tools.
- Consulting, services, or forward-deployed engineering management experience is a bonus.
How the team works
The company emphasizes high trust, individual agency, low ego, and sharing lessons learned.
AI agents generate much of the client code, while engineers review outputs and remain accountable.
The manager is expected to engage with clients and contribute a point of view on important decisions.
Compensation
- Base salary is $300,000 USD plus competitive equity; monthly wellness stipend is also offered.
Workplace
- Hybrid in New York City and fully remote in the rest of the United States and Canada.
Benefits
- Benefits include 401(k) matching, covered medical, dental, and vision premiums, parental leave, and commuter benefits.
- A Soho office offers lunch and snacks.
Interview process
- The process includes recruiting and technical screens, a hiring manager interview, technical interviews, and a live case study.
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