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Engineering Manager, Applied AI

HeadstartNew York, NYEngineering
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Salary
$285K
Job type
Full-time
Work mode
Remote
Experience
Senior · 3+ yrs
Posted
29 Sept 2026
Status
Open · checked 7d ago

About this role

The Engineering Manager, Applied AI position at Headstart in New York, NY (or remote within the US or Canada) suits an experienced software leader with a background in engineering management and client delivery who wants to build production AI systems for major enterprises. This professional splits time between hands-on client engagements and managing a team of software engineers.

Role Overview

The Engineering Manager, Applied AI reports to the Head of Engineering and leads a group of engineers across multiple client projects. The position involves maintaining high technical standards, mentoring direct reports, steering engagement delivery, and participating in hiring. Team members work directly with large enterprises to solve complex operational challenges using production artificial intelligence systems.

Key Responsibilities

Manage software engineers up to senior level, delivering direct feedback and coaching individuals toward tech lead paths.
Oversee technical execution by reviewing architecture, agent designs, prompt structures, and evaluation frameworks.
Lead engagement-level relationships with client stakeholders alongside product and client partners.
Handle team staffing, plan transitions, and flag potential delivery risks early.
Interview, calibrate, close, and onboard incoming engineering talent.
Share recurring patterns with the broader team to establish standing internal practices.

Requirements

Minimum of 3 years of experience managing software engineers, including people development and performance feedback.
At least 5 years of professional software engineering experience with hands-on proficiency in Python.
Prior background delivering software solutions within real client environments.
Familiarity with agents, evaluations, multi-agent systems, and AI coding tools.

Nice to Have

Management experience within a consulting, professional services, or forward-deployed engineering organization.
Experience building a team or practice from the ground up.

Skills and Tools

Python
AI coding tools
Agent systems
Evaluation frameworks

Salary and Benefits

Base salary of $285,000 USD accompanied by competitive equity.
401(k) plan featuring a 4.5% employer match.
Fully covered medical, dental, and vision insurance premiums.
Monthly wellness stipend, Citi Bike membership, and pre-tax commuter benefits.
12 weeks of parental leave with an optional 4-week ramp-up period at 50% time.
Access to a loft office in Soho featuring provided lunch and snacks for hybrid staff in New York City.

About the Company

Headstart creates production artificial intelligence systems for enterprises operating at $100M+ in ARR across various industries. The organization is bootstrapped, cash-flow positive, and scaling rapidly while developing its proprietary platform for agentic systems.

How to Apply

Interested candidates should apply on the official company careers page.

Skills and tech stack

Questions candidates ask

Where is this job located?

This role is based in a Soho loft office in New York, NY with a hybrid schedule, or open to fully remote candidates located in the US or Canada.

How many years of management experience are required?

Candidates must have at least 3 years of experience managing software engineers.

What programming language is required for this role?

Hands-on experience with Python is required.

What are the salary and financial compensation details?

The base salary is $285,000 USD, plus competitive equity and a 401(k) with a 4.5% employer match.

What does the interview process involve?

The process includes an initial recruiting screen, a technical coding screen, a hiring manager interview, two technical interviews covering coding and systems design, and a final case study discussion.

Ready to apply?

The application is on the official Headstart careers page.

Apply on company site