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Senior Engineering Manager, Applied AI

HeadstartNew York, NYEngineering
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Salary
$300K
Job type
Full-time
Work mode
Remote
Experience
Senior · 8+ yrs
Posted
29 Sept 2026
Status
Open · checked 7d ago

About this role

This Senior Engineering Manager role suits an experienced software leader with a background in management and client environments who wants to build production AI systems in New York, NY or remotely across the US and Canada. Headstart seeks a leader to guide engineering teams, deliver client solutions, and drive hiring for applied artificial intelligence initiatives.

Role Overview

Headstart is hiring a Senior Engineering Manager, Applied AI for a hybrid position based in New York, NY or fully remote across the United States and Canada. The person in this position begins on a client engagement to understand workflows before building and leading a team. The company operates as a bootstrapped, cash-flow-positive enterprise focused on deploying production artificial intelligence systems into real businesses.

Key Responsibilities

Build and lead a team while providing direct feedback and growing senior engineers into tech leads.
Review architecture, agent designs, prompts, and evaluations while navigating difficult technical situations.
Turn patterns from client engagements into standing practices, reference implementations, and platform capabilities.
Manage staffing, plan project transitions, and direct hiring from sourcing to onboarding.
Partner closely with product teams, client partners, and client stakeholders.

Requirements

Minimum of 4 years of experience managing engineers, including senior and staff levels, with a track record of hiring and professional development.
Minimum of 8 years of professional software engineering experience with hands-on Python proficiency.
Experience delivering software within real client environments and taking initiatives from zero to one.
Familiarity with AI coding tools, agents, evaluations, and multi-agent systems.

Nice to Have

Management experience within a consulting, services, or forward deployed engineering organization.

Skills and Tools

Python
AI coding tools
Agents
Evaluations
Multi-agent systems
Friday (coding agent)
Statum (knowledge infrastructure)

Salary and Benefits

Base salary of $300,000 USD with competitive equity.
401(k) with a 4.5% employer match.
Fully covered medical, dental, and vision premiums.
Monthly wellness stipend, Citi Bike membership, and pre-tax commuter benefits.
12 weeks of parental leave with an optional 4-week ramp-up at 50%.
Loft office access in Soho featuring provided lunch and snacks.

About the Company

Headstart builds production artificial intelligence systems for enterprises with over $100 million in Annual Recurring Revenue. The organization is bootstrapped, cash-flow positive, and develops its own platform to deliver agentic systems. Team members work across diverse industries and complex enterprise constraints.

How to Apply

Candidates should apply on the official company careers page.

Skills and tech stack

Questions candidates ask

Where is the Senior Engineering Manager, Applied AI position located?

The role offers hybrid work in a Soho loft office in New York, NY, or fully remote work across the rest of the United States and Canada.

What is the base salary for this position?

The base salary is $300,000 USD, supplemented by competitive equity.

What level of experience is required for this role?

Candidates need at least 8 years of software engineering experience and 4 or more years of management experience overseeing engineers.

What does the interview process look like?

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

What benefits are included with employment?

Benefits include fully covered medical, dental, and vision insurance, a 401(k) with a 4.5% match, a monthly wellness stipend, pre-tax commuter benefits, Citi Bike access, and 12 weeks of parental leave.

Ready to apply?

The application is on the official Headstart careers page.

Apply on company site