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Head of Engineering (backed by Y Combinator, $5M+ ARR, $23M+ raised)

legionhealthSan FranciscoEngineering
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Salary
$250K – $400K
Job type
Full-time
Experience
Senior · 10+ yrs
Posted
16 Sept 2026
Status
Open · checked 7d ago

About this role

This role suits an experienced engineer who thrives on owning entire complex problem spaces independently and shipping production systems at high velocity in San Francisco. Head of Engineering at Legion Health is a principal-level position responsible for building autonomous medical care infrastructure and scaling engineering operations.

Role Overview

Legion Health is hiring a Head of Engineering in San Francisco to own critical architecture across their regulated clinical care platform. The position suits a hands-on technical leader with a staff-plus IC, chief-architect, or platform-consulting background who prefers building over managing and can take ambiguous, load-bearing problems from conception to completion.

Key Responsibilities

Own the factory spine by scaling merge gates, migration safety, canary deployments, and rollbacks to support high-volume PR merges.
Manage the clinical work spine, maintaining an event-sourced system of record for orders, tasks, and commands with auditability and fail-closed checks.
Direct production agent operations, establishing how LLM agent autonomy expands and safely handles clinical-adjacent tasks.
Oversee the data and analytics estate, including the warehouse, analytics platform, and pipelines.
Partner directly with leadership on architecture synchronization, making domain calls and communicating decisions clearly.

Requirements

Experience owning architecture across multiple companies or codebases in a staff-plus IC, chief-architect, or platform-consulting capacity.
Demonstrated ability to ship daily at high volume using a fleet of AI agents with unsupervised workflows.
Track record of taking ambiguous and load-bearing problems whole, building solutions, and documenting them independently.
Strong proactive written communication habits.
Ability to maintain clinical-grade correctness, auditability, HIPAA compliance, and fail-closed defaults without sacrificing speed.

Skills and Tools

TypeScript
Node.js
Postgres
Next.js on Vercel
AWS
Production LLM agent orchestration and bespoke harnesses
EHR and e-prescribing integrations
PHI-grade security and audit trails

Salary and Benefits

Salary range of $250,000 to $400,000 depending on experience
Early-stage equity
Medical, dental, and vision health insurance benefits
Meal stipends and in-person retreats
Flexible, unlimited vacation policy

About the Company

Legion Health is building autonomous medical care, starting with psychiatry, backed by Y Combinator and prominent venture capital firms and founders. The company provides a regulated clinical product that e-prescribes controlled substances, operating with an AI-native care-delivery platform that automates administrative work and lowers clinical labor costs.

How to Apply

Apply on the official company careers page.

Skills and tech stack

Questions candidates ask

Where is the Head of Engineering role located?

The role is based in-person at the San Francisco headquarters, though partial remote work may be considered for exceptional candidates.

What is the salary and compensation structure?

The salary ranges from $250,000 to $400,000 depending on experience, and includes early-stage equity, medical, dental, and vision insurance, meal stipends, and unlimited vacation.

Is visa sponsorship available for this position?

Yes, US visa sponsorship is available.

What technical stack does Legion Health use?

The tech stack includes TypeScript, Node.js, Postgres, Next.js on Vercel, AWS, production LLM agent orchestration, EHR integrations, and PHI-grade security tools.

Is this a management role?

No, this is a senior individual contributor seat focused on building rather than managing, intended for someone who takes on entire problem spaces independently.

Ready to apply?

The application is on the official legionhealth careers page.

Apply on company site