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

At Legion Health we believe everyone deserves fast affordable and world-class health care and were developing the AI infrastructure to deliver it ourselves at world scale.

Legion is building autonomous medical care (the AI doctor) starting with psychiatry. Our AI-native care-delivery platform currently automates 95% of the administrative work required for us to deliver direct patient care. We also recently became the first company ever to receive regulatory authorization to let AI prescribe psychiatric medications allowing us to not only collapse health cares admin costs but also its clinical labor costsshifting this industrys economics from humans to tokens.

Our technical moat is hard to copywe combine rich data production AI doctors in the loop and end-to-end care operations to deliver measurably better care to a clinically complex patient population. This has helped us produce tens of thousands of total visits in just 2 years all while holding ops costs flat and achieving industry-leading patient NPS and retention. While the last generation of healthcare startups made the existing system incrementally more efficient Legion is rebuilding full-stack care delivery from first principles. Our vision A 10X better patient experience thats higher quality less expensive and more scalable than ever before. And a 10X better clinician experience that frees our providers to focus on what matters most: caring for patients.

Legion Health is backed by Y Combinator leading venture capital firms and founders from Function Health Modern Health Everly Health Trusted Health Clipboard Health PatientPing Sesame Care Faire EasyPost and fuboTV.

Join us as we build the future of health care: faster higher-quality and more affordable powered by doctors and AI working together.

Hey Im Daniel G Wilson co-founder and CTO at Legion. I studied applied math and CS at Princeton led the Office Scripts and Power Automate integration at Microsoft and did deep learning and RL research before that. GitHub: hiring a principal-level engineer to own the hardest systems in our care platform whole. Not tickets not a lane inside someone elses architecture: entire problem spaces from this is a mess to this is done and heres the doc.

Heres the honest shape of the job. We run a regulated clinical product (we e-prescribe controlled substances) on an event-driven TypeScript platform and we ship at unusual velocity with heavy agent leverage. The engineers who have thrived here share one behavior: I hand them a gnarly domain they disappear into it and they come back with it working documented and theirs. I dont need to check their work or meddle because checking isnt unnecessary. Thats the seat. The people who have struggled here waited for scoped tickets to tell them what to dobut thats what we have agents for.

Real domains picked together in week one from this list with written authority over them:

• The factory spine. Own the question of how we get maximum leverage in the era of agentic engineering. We shipPRs a month with a lean team. Merge gates migration safety canary and rollback on a system where a bad deploy can touch patient carethis all works today. Your job will be to move us towards 10000 while maintaining quality and rigor.

• The clinical work spine. Our event-sourced system of record for clinical work (orders tasks commands receipts): the layer that lets AI agents and humans act on patient care with auditability and fail-closed checks. Youll own the guardrails that ensure agents can safely provide broader and broader components of care.

• Agent operations in production. LLM agents doing real clinical-adjacent work with tool use checks and receipts. You decide how autonomy expands and ratchets upwards as proof accumulates. Your agent harness will help prescribe psychiatric medication legally at the second company ever allowed to.

• The data and metrics estate. Warehouse analytics platform and the pipelines that tell us what actually happened.

• Architecture syncs with me. Youll have the standing I give someone who has seen more systems than I have: disagree with me make the call in your domain unpack it for the team when asked.

• Youve owned architecture across multiple companies or many codebases: staff-plus IC chief-architect or platform-consulting background. Youve seen a dozen ways teams ship and you have opinions with scars behind them.

• You ship daily at high volume with a fleet of AI agents. Thats table the interview well ask to see your actual setup and what you let it do unsupervised. I use Copilot sometimes is not this.

• When handed an ambiguous ugly load-bearing problem your instinct is to take it whole: read everything decide build write the doc tell us what you decided. Not to schedule a meeting about scope.

• You communicate proactively in writing. The pattern we love: a Sunday text that says took care of it heres the PR and what I changed.

• You hold clinical-grade correctness without losing speed: auditability HIPAA fail-closed defaults invariants over vibes.

This is a senior seat. Typically that means 10 years and multiple systems owned end to end but we care about the scars not the number. We have separate openings for earlier-career engineers; this is not that. We need someone whos seen some shit.

This role is not for you if you want to manage instead of build you need well-scoped tickets to be productive or big-company pace feels normal to you.

• TypeScript Postgres on Vercel AWS production LLM agent orchestration and bespoke harnesses tools CLIs skills evals and observability EHR and e-prescribing integrations PHI-grade security and audit trails.

• Job type: Full-time

• Role type: Engineering

• US Visa Sponsorship: Yes

• Salary: $250000 to $400000 depending on experience plus meaningful early-stage equity.

• Health Insurance: Medical dental and vision benefits

• Additional Perks: In-person retreats meal stipends etc.

• Time Off: Flexible unlimited vacation policy

• Work hours: flexible but demandingbecause we are (literally) saving lives.

• Work Setup: In-person @ San Francisco HQ; partial remote considered for exceptional candidates (our track record includes both).

• Impact: Work on something that truly matters to millions of patients and families.

• Autonomy and Learning: Ownership over your projects with the freedom to set priorities shape processes and drive outcomes end-to-end.

• Growth Opportunities: As we scale we envision our top performers stepping into expanded roles and joining our executive leadership team.

Legion Health is proud to be an Equal Opportunity Employer. We celebrate diversity and are committed to creating an inclusive environment for all employees contractors and applicants without regard to race color religion sex sexual orientation gender identity or expression national origin age disability veteran status genetic information or any other protected characteristic under applicable law. We encourage applicants from all backgrounds to apply.

Required Experience:

Director