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

Legion is hiring a Head of Product to own the consumer product experience that turns AI-native care delivery into something patients can understand, trust, use, and return to.

This is not a technical program management role, an enterprise roadmap coordinator role, or a “growth PM” role with healthcare language added on top. You will own real product surface area across Legion’s patient journey: onboarding, intake, eligibility, scheduling, visit prep, provider matching, care-plan clarity, medication workflows, follow-up, renewals, messaging, reactivation, and the moments that make a patient feel safe enough to come back.

The right person is technical enough to reason through APIs, data models, event instrumentation, AI workflows, edge cases, system constraints, and engineering tradeoffs, but consumer-minded enough to know that the best product often feels obvious, calm, and human. You should be able to sit with a patient problem, map the underlying clinical and operational workflow, write a crisp product spec, prototype the interaction, instrument the funnel, partner deeply with engineering and design, ship the feature, and decide whether it actually improved care.

Legion is a modern consumer AI software company that happens to deliver medical care. That means the product bar is closer to Anthropic, OpenAI, Character.AI http://Character.AI, Replit, Oura, WHOOP, Duolingo, Chime, Monarch, and the best consumer health companies than to traditional healthcare software. We need someone who can bring that level of product taste, technical speed, and retention thinking into a regulated, high-trust category where quality and safety matter.

This is a high-ownership IC role with founder-level visibility and a direct path to management of a large product organization. You will work directly with engineering, design, clinical, operations, growth, data, compliance, and the founders to turn messy real-world care delivery into simple, powerful product experiences.

Responsibilities and deliverables

• Own core patient-facing product surfaces across the full consumer journey: discovery, onboarding, intake, insurance/payment clarity, scheduling, provider fit, visit prep, visit completion, follow-up, care-plan adherence, refills, renewals, messaging, support, retention, and reactivation.
• Translate complex clinical, operational, regulatory, and AI workflows into simple consumer experiences that reduce anxiety, increase clarity, and help patients know exactly what to do next.
• Build durable product systems, not one-off features: patient timeline, care status, tasking, reminders, notifications, escalation paths, asynchronous messaging, support deflection, eligibility logic, provider availability, and follow-up workflows.
• Partner with engineering to scope and ship technically sound products across web, mobile-responsive experiences, backend workflows, APIs, third-party integrations, event pipelines, data models, and AI-assisted workflows.
• Define and own product metrics for your surface area, including activation, intake completion, scheduling conversion, first-visit completion, time to care, repeat-visit rate, renewal completion, retention, NPS/CSAT, patient confusion, support burden, no-shows, and ops cost per visit.
• Use PostHog, SQL, analytics tools, customer support data, operational dashboards, and qualitative research to identify patient friction, prioritize product bets, and measure whether shipped work moved the right metrics.
• Design and run structured experiments where appropriate, while knowing when a healthcare product needs principled product judgment, clinical input, and quality thresholds instead of pure A/B testing.
• Own product specs, user stories, acceptance criteria, rollout plans, QA checklists, experiment plans, metric definitions, launch notes, and post-launch readouts with enough clarity that engineering, clinical, ops, and growth can all execute cleanly.
• Prototype quickly using Figma, v0, Lovable, Replit, Cursor, Codex, Claude Code, lightweight scripts, no-code tools, or whatever helps you make product ideas concrete before engineering invests real cycles.
• Ship production PRs regularly. This is a product role—not a software-engineering role—but you are expected to work directly in the codebase and open production-quality PRs for well-scoped changes such as instrumentation, internal tools, workflow logic, UI and copy improvements, prototypes, and small fixes. You should be comfortable testing, reviewing, and safely rolling out your work in close partnership with engineering.
• Partner with clinical and operations teams to deeply understand real patient and provider workflows, including edge cases: missed appointments, medication refill timing, insurance confusion, state/provider availability, pharmacies, clinical escalations, patient safety concerns, handoffs, and support loops.
• Partner with compliance, legal, privacy, and clinical leadership to design AI-enabled product experiences with appropriate safeguards, human review, auditability, expectation-setting, and patient trust.
• Improve Legion’s AI product layer: patient-facing AI interactions, AI-assisted intake, personalization, care navigation, workflow automation, internal copilots, clinical/ops review queues, and evaluation loops that make automation safer and more useful over time.
• Create product feedback loops from patient conversations, support tickets, provider feedback, drop-off data, session recordings, funnel analytics, and clinical/ops metrics so the roadmap is grounded in real behavior, not vibes.
• Work with growth and brand to ensure acquisition promises match the actual product experience, so the patients we bring in understand what Legion does, feel properly oriented, and are more likely to stay in care.
• Raise the product craft bar across Legion: clearer flows, better defaults, fewer dead ends, tighter copy, sharper state handling, cleaner mobile experiences, stronger instrumentation, faster iteration, and more rigorous launch quality.

You’ll be successful if you

• Make Legion’s patient experience feel consumer-grade: fast, clear, calm, trustworthy, and easy to return to.
• Improve the core retention loop of care: more patients complete intake, make it to their first visit, understand the next step, follow through on care plans, complete renewals when eligible, and come back when they need help.
• Turn messy clinical and operational workflows into product systems that scale without making patients feel like they are navigating a maze.
• Ship AI-enabled experiences that feel useful and safe, with clear boundaries around what AI does, what doctors do, and when humans review or intervene.
• Build a measurement system that makes the patient journey legible: every meaningful step has an owner, a metric, and a path to improvement.
• Reduce patient confusion and support burden by improving the product itself, not just by adding more manual operations.
• Help Legion move faster without becoming sloppy: strong specs, smart scoping, crisp decisions, high-quality launches, and honest post-launch learning.
• Earn trust from engineering because you understand technical constraints and tradeoffs, and from clinical/ops teams because you understand the reality of care delivery.
• Create product experiences that are emotionally intelligent without being soft, technically sophisticated without being confusing, and ambitious without being reckless.
• Help build the product foundation for a company that can deliver world-class medical care at dramatically lower cost.

• 5+ years of product management, product engineering, technical founder, or equivalent experience, with meaningful ownership of consumer-facing web or mobile products.
• Strong consumer product instincts. You have shipped products that people actually use, understand, trust, and return to, not just internal tools or enterprise workflows.
• Technical fluency across software product development. You can reason through APIs, data models, event instrumentation, backend workflows, frontend states, AI workflows, latency, failure modes, privacy constraints, and engineering tradeoffs.
• Hands-on technical curiosity. You can navigate API docs, logs, event payloads, session recordings, agent traces, and enough of a codebase to understand what is really happening without pulling engineers into every first-pass investigation.
• Experience partnering deeply with engineering and design from problem definition through launch: discovery, PRDs/specs, UX flows, technical scoping, sprint planning, QA, rollout, metric tracking, and iteration.
• Strong analytical ability. You are comfortable with SQL or equivalent data exploration, product analytics tools such as PostHog, Amplitude, Mixpanel, Looker, Hex, or Mode, and you can define useful metrics without waiting for someone else to hand you a dashboard.
• Track record improving engagement, retention, activation, conversion, habit formation, lifecycle, or core experience metrics in a consumer product.
• High product taste and UX judgment. You care about copy, information architecture, interaction design, empty states, error states, mobile responsiveness, notification timing, trust cues, and the emotional texture of the user experience.
• AI-native working style. You already use tools like Codex, Claude Code, Cursor, Replit, Lovable, v0, ChatGPT, Claude, Figma AI, or similar tools to prototype, analyze, write, synthesize, debug, and move faster.
• Comfort working on AI-enabled products where the PM must think about prompt behavior, user expectations, evaluation, quality thresholds, fallback paths, human review, auditability, and safety.
• Healthcare experience is a strong plus but not required. Experience in another trust-sensitive consumer category such as fintech, insurance, family/kids, identity, privacy, marketplaces, wellness, or regulated consumer products is also valuable.
• Startup operating mode: high agency, low ego, high urgency, strong writing, strong judgment, strong follow-through. You can create clarity without waiting for a perfect org chart.
• Ability to work cross-functionally with clinical, operations, support, compliance, legal, growth, data, design, engineering, and founders without losing the thread of the user problem.
• Excellent writing. You can write crisp strategy docs, product specs, launch plans, decision memos, patient-facing copy, and post-launch analyses.

• Job Type: Full-Time
• Role Type: Product / Technical Product Management / Consumer AI / Patient Experience / Retention
• Ideal Experience Level: 5+ years
• Location: San Francisco
• US Visa Sponsorship: Yes

• Apply here: https://jobs.ashbyhq.com/legionhealth/0ffded39-1242-4a35-9bc3-0e5b0ce22276
• Overview of our hiring process:
• Resume + Application Screen
• Founder / Product Interview
• Technical Product Deep Dive
• Cross-Functional Interviews with Engineering, Design, Clinical/Ops, Growth, and Founders
• Professional Reference Checks
• Estimated time-to-hire: 2 weeks
• Start date: ASAP
• Hiring manager: Arthur MacWaters

• Salary: $190,000 – $330,000
• Early-Stage Equity: Meaningful ownership in a category-defining company.
• Health Insurance: Medical, dental, and vision benefits
• Additional Perks: In-person retreats, meal stipends, AI/product tooling budget, learning stipend, home office support
• Time Off: Flexible, unlimited vacation policy
• Work Hours: Flexible
• Work Setup: In-person in San Francisco
• Impact: Build the product layer for a company trying to change health care forever.
• Autonomy and Learning: Own major patient-facing product surfaces end-to-end, from product strategy through technical scoping, launch, measurement, and iteration.
• Growth Opportunities: As we scale, this role can grow into Chief Product Officer.

At Legion Health https://legionhealth.com/, we believe everyone deserves fast, affordable, and world-class health care, and we’re 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 https://nypost.com/2026/03/27/business/artificial-intelligence-can-now-prescribe-mental-health-drugs/, allowing us to not only collapse health care’s admin costs but also its clinical labor costs—shifting this industry’s economics from humans to tokens.

Our technical moat is hard to copy—we 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 that’s 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.