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

Legion Health • San Francisco, CA

26d • $250,000 - $400,000 • Hybrid

About The Position

Legion Health is building the AI infrastructure to deliver fast, affordable, and world-class healthcare, starting with psychiatry. Their AI-native care-delivery platform automates 95% of administrative work and has received regulatory authorization for AI to prescribe psychiatric medications. They combine rich data, production AI, doctors in the loop, and end-to-end care operations to deliver measurably better care. Legion Health is backed by Y Combinator and other leading venture capital firms.

Requirements

• Owned architecture across multiple companies or many codebases (staff-plus IC, chief-architect, or platform-consulting background).
• Experience shipping daily at high volume with a fleet of AI agents.
• Instinct to take whole ambiguous, ugly, load-bearing problems: read everything, decide, build, write the doc, and communicate decisions.
• Proactive written communication skills.
• Ability to hold clinical-grade correctness (auditability, HIPAA, fail-closed defaults, invariants) without losing speed.
• Typically 10+ years of experience and multiple systems owned end to end.
• Experience with regulated clinical products and event-driven TypeScript platforms.
• Experience with LLM agent orchestration and bespoke harnesses, tools, CLIs, skills, evals and observability.
• Experience with EHR and e-prescribing integrations.
• Experience with PHI-grade security and audit trails.

Nice To Haves

• Experience in a fast-paced startup environment.
• Experience with TypeScript, Node.js, Postgres, Next.js on Vercel, AWS.

Responsibilities

• Own the hardest systems in our care platform, entire problem spaces, from 'this is a mess' to 'this is done and here's the doc.'
• Own the factory spine, focusing on how to get maximum leverage in the era of agentic engineering and moving towards shipping 10,000 PRs a month while maintaining quality and rigor.
• Own the clinical work spine, the event-sourced system of record for clinical work, ensuring auditability and fail-closed checks for AI agents and humans.
• Own agent operations in production, deciding how autonomy expands and ratchets upwards as proof accumulates, and managing the agent harness for prescribing psychiatric medication.
• Own the data and metrics estate, including the warehouse, analytics platform, and pipelines.
• Conduct architecture syncs with the CTO, having the authority to disagree, make calls within their domain, and unpack decisions for the team.

Benefits

• Medical, dental, and vision benefits
• In-person retreats
• Meal stipends
• Flexible, unlimited vacation policy
• Meaningful early-stage equity
• Ownership over projects with freedom to set priorities, shape processes, and drive outcomes end-to-end.
• Opportunities to step into expanded roles and join the executive leadership team as the company scales.

What This Job Offers

• Job Type: Full-time
• Career Level: Principal
• Education Level: No Education Listed