Engineering Manager, Applied AI
Role Overview
This is a player-coach and staffing partner role reporting to the Head of Engineering.
The manager remains hands-on in a client engagement while managing engineers across multiple engagements.
Key Skills for This Role
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About Headstart
Headstart builds production AI systems for enterprise clients and is developing its own platform for agentic systems.
The company describes its work as high-trust, high-agency, and AI-first, with human review and accountability for AI-generated output.
Role overview
This is a player-coach and staffing partner role reporting to the Head of Engineering.
The manager remains hands-on in a client engagement while managing engineers across multiple engagements.
What you will own
- Manage and develop engineers up to senior level through a high performance bar, direct feedback, and coaching.
- Review architecture, agent, prompt, and evaluation designs; resolve difficult technical or client situations and raise risks early.
- Lead client and stakeholder relationships for engagements alongside product and client partners.
- Plan team transitions and staffing, identify risks, and escalate cross-engagement conflicts.
- Interview, calibrate, close, and onboard engineers.
- Follow team practices, identify improvements, share useful patterns, and ensure the team applies existing practices.
Required background
- 3+ years managing engineers, with experience giving feedback and developing people.
- 5+ years in software engineering, sufficient to review designs and challenge technical approaches.
- Hands-on Python experience and experience delivering software in client environments.
- Curiosity about agents, evaluations, and multi-agent systems, including understanding reliability and when human judgment is needed.
- Fluency with AI coding tools.
Bonus experience
- Management experience in consulting, services, or a forward-deployed engineering organization is a bonus.
- Experience taking a team or practice from zero to one is a bonus.
Work arrangement
- The company describes the role as hybrid in New York City and open to fully remote candidates in the United States or Canada.
Compensation and benefits
- Base salary is $285,000 USD plus competitive equity.
- Benefits include a 401(k) with 4.5% employer match, covered medical, dental, and vision premiums, wellness and commuter benefits, and 12 weeks of parental leave.
- The company offers an office in SoHo with lunch and snacks.
Interview process
- The process includes recruiting and technical screens, a hiring manager interview, technical interviews in coding and systems design, and a live case study.
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