Staff Engineer, Applied AI — Lead End-to-End AI Systems

Headstart; New York (NY); Hybrid; USD 239,000 - 292,000; Full time

Benefits offered by this job

Equity compensation

401k with employer match

Medical, dental, and vision benefits

Wellness stipend

Pre-tax commuter benefits

Job summary

Headstart is seeking an accomplished software leader to own end-to-end client engagements, guiding architecture, scope, and delivery. You will serve as the technical authority in executive conversations and drive the platform forward with high-leverage investments in tooling and infrastructure.

You will grow and coach engineers, balance multiple engagements, and design distributed systems at scale. This role favors founders’ mindset and startup experience, with a heavy emphasis on reliability,

Qualifications

• 7+ years of professional software engineering experience with a track record of owning complex, high-stakes systems end-to-end.
• Have owned client relationships at the executive level: running discovery, navigating difficult conversations, and earning trust quickly.
• Been the technical authority in rooms with executives and clients and have shaped what got built, not just built what you were told.
• Have designed and shipped agentic systems to solve complex user challengers, and knowing when to lean on deterministic solutions.

Responsibilities

• Operate as technical lead on complex and ambiguous client engagements end-to-end, from ideation and discovery through to production.
• Be the technical authority in sales and scoping conversations.
• Shape client strategy by reframing problems, influencing priorities, and defining what the right path forward looks like.
• Build 0 -> 1 rapidly while ensuring long-term reliability, maintainability, and security.
• Balance multiple concurrent engagements, context-switching between different technical stacks and business domains.
• Contribute to the Headstart Platform by identifying and delivering high leverage investments across our tooling and infrastructure.
• Grow the engineers around you and act as player-coach to raise the floor of every project you work on.

Skills

Software engineering

Executive stakeholder management

Systems design

Distributed systems

Full-stack development

Tools

Python

React

Next.js

ML (optional)

Job description

Headstart is seeking an accomplished software leader to own end-to-end client engagements, guiding architecture, scope, and delivery. You will serve as the technical authority in executive conversations and drive the platform forward with high-leverage investments in tooling and infrastructure.

You will grow and coach engineers, balance multiple engagements, and design distributed systems at scale. This role favors founders’ mindset and startup experience, with a heavy emphasis on reliability,