Applied AI Engineering Manager — Remote/Hybrid

Headstart; New York (NY); Hybrid; USD 257,000 - 314,000; Full time

Benefits offered by this job

401k match

Medical dental vision

Wellness stipend

Parental leave 12 wks

Loft office Soho

Hybrid in NYC

Remote US/Canada allowed

Job summary

Headstart is building AI-powered systems for large enterprises, shipping production-grade agents and multi-agent workflows. We’re seeking a senior engineering leader who can mentor engineers, own engagements, and raise the bar on technical excellence.

You’ll guide architecture reviews, manage client relationships, and scale a growing team across multiple engagements, while staying hands-on with Python and system design.

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.
• Bonus: management experience in a consulting, services, or forward deployed engineering organization, or experience taking a team or practice from zero to one.

Responsibilities

• Your engineers: manage engineers up to senior, provide 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

Python

Software engineering

Code review

Client delivery experience

AI familiarity

Job description

Headstart is building AI-powered systems for large enterprises, shipping production-grade agents and multi-agent workflows. We’re seeking a senior engineering leader who can mentor engineers, own engagements, and raise the bar on technical excellence.

You’ll guide architecture reviews, manage client relationships, and scale a growing team across multiple engagements, while staying hands-on with Python and system design.