Senior Engineering Manager — Lead AI Teams (Remote)

Headstart; New York (NY); Hybrid; USD 270,000 - 330,000; Full time

Benefits offered by this job

401k match

Medical coverage

Dental coverage

Vision coverage

Wellness stipend

Citi Bike usage

Job summary

Headstart is seeking a seasoned engineering leader in NYC to guide cross-functional teams delivering production AI systems for enterprise clients. You will mentor engineers, drive architecture decisions, and shape how engagements scale across industries.

You will own staffing, hiring, and partnerships, ensuring high-quality delivery while maintaining a strong client-focused mindset. Hybrid role with onsite NYC presence and remote options across the US/Canada.

Qualifications

• 4+ years managing engineers, including senior and staff.
• 8+ years in software engineering, hands-on with Python.
• Experience delivering software in real client environments and taking something from zero to one.
• Curious about agents, evals, and multi-agent systems, with a sense of reliability and when a person should lead.

Responsibilities

• Lead your team with high standards and growth focus; provide direct, actionable feedback.
• Provide technical leadership: review architecture, agent, prompt, and eval design; handle tough client scenarios.
• Identify patterns across engagements and turn them into reusable practices and platform capabilities.
• Shape who works on which engagement, plan transitions, and flag risks before they reach a client.
• Run hiring for your team, from sourcing to onboarding; define the bar.
• Collaborate with product, client partners, and stakeholders so each engagement lands.

Skills

Engineering leadership

Python

Client delivery experience

AI tooling

Job description

Headstart is seeking a seasoned engineering leader in NYC to guide cross-functional teams delivering production AI systems for enterprise clients. You will mentor engineers, drive architecture decisions, and shape how engagements scale across industries.

You will own staffing, hiring, and partnerships, ensuring high-quality delivery while maintaining a strong client-focused mindset. Hybrid role with onsite NYC presence and remote options across the US/Canada.