Applied AI Engineering Manager — Enterprise Systems

Headstart AI; New York (NY); Hybrid; USD 242,000 - 328,000; Full time

Benefits offered by this job

Base salary $285,000 USD

401k with 4.5% employer match

Medical, dental, and vision premiums

Monthly wellness stipend

Citi Bike benefit

Pre-tax commuter benefits

12 weeks parental leave

Loft office in Soho

Hybrid in NYC / remote US/Canada

Job summary

Headstart AI in New York City is seeking a senior engineering leader to manage and grow a team delivering production AI systems for enterprise clients. You will lead engineers across multiple engagements, ensure high-quality technical outcomes, and maintain close client relationships to land engagements successfully.

The role requires 5+ years in software engineering and 3+ years of people management, with hands-on Python and a passion for agents, evals, and multi-agent systems.

Qualifications

• 3+ years managing engineers, with real experience giving feedback and developing people.
• 5+ years in software engineering, deep enough to review designs and challenge the team's approach. Hands-on with Python.
• Experience delivering software in real client environments.
• Curious about agents, evals, and multi‑agent systems, with a sense of where they're reliable and where a person needs to take the wheel. Fluent with AI coding tools. Depth matters more than prior title.

Responsibilities

• Your engineers. Manage engineers up to senior, hold a high bar, and give direct, actionable feedback. Coach on execution and help strong engineers step up toward tech lead.
• Technical leadership. Review architecture, agent, prompt, and eval design on your engagements. Step into hard technical and client situations, like production regressions and unclear requirements, and make the call. Raise trouble early, while it's cheap to fix.
• Engagement delivery. Run the engagement-level relationship with clients and their stakeholders, alongside product and client partners, so each engagement lands.
• Staffing. Manage transitions on your team, plan ahead, and flag risks before they reach a client. Escalate conflicts across engagements to the Head of Engineering.
• Hiring. Interview, calibrate, close, and onboard new engineers against the bar the Head of Engineering sets.
• Practice. Follow the team's practices and tell us what isn't working. Bring patterns you see to the wider team so they can become standing practice, and make sure your engineers use what exists.

Skills

People management

Software engineering

Client engagement

AI tooling familiarity

Tools

Python

Job description

Headstart AI in New York City is seeking a senior engineering leader to manage and grow a team delivering production AI systems for enterprise clients. You will lead engineers across multiple engagements, ensure high-quality technical outcomes, and maintain close client relationships to land engagements successfully.

The role requires 5+ years in software engineering and 3+ years of people management, with hands-on Python and a passion for agents, evals, and multi-agent systems.