5 Headway Doctors Jobs Hiring Near You

At Legion Health, 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, 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.

• Job Type: Full-Time

• Role Type: Lifecycle Marketing / CRM / AI-Native Patient Engagement / Retention / Growth

• Ideal Experience Level: 6+ years, including 3+ years owning lifecycle, CRM, retention, or owned-channel growth

• Location: In-Person in San Francisco, CA

• US Visa Sponsorship: Yes

Legion is hiring an AI Lifecycle Product and Marketing Leader to build the AI-native patient communication engine that helps people start care, stay in care, come back when they lapse, and feel personally supported across months and years of treatment.

This is not a typical lifecycle marketing job. We are not looking for someone to manage a static email calendar, build a few drip campaigns, and optimize subject lines. Legion has rich patient data, production AI, clinical workflows, scheduling events, insurance data, intake behavior, appointment history, medication renewal patterns, and care operations all inside one vertically integrated system. That means we can build something far more powerful: a personalized, proactive communication engine that knows where each patient is in their journey and automatically helps move them to the next right step.

You will build the system that makes Legion feel impossibly responsive. A patient who stalls in intake should get the right nudge. A patient who books but does not complete prep should get the right reminder. A patient at risk of missing follow-up should be guided before they lapse. A patient due for renewal should understand what to do next. A patient who churned should receive a thoughtful, relevant path back. Over time, the engine should become more intelligent, more personalized, and more autonomous.

The right person combines the lifecycle rigor of DoorDash, Instacart, Airbnb, or Sephora; the patient-journey discipline of Hims, Thirty Madison, Headway, or Talkiatry; the retention instincts of Noom, Peloton, WHOOP, or Duolingo; and the AI-native curiosity required to build communication systems that can generate, personalize, test, and improve patient journeys at scale.

This is a founding systems-builder role. You should be comfortable designing lifecycle strategy, mapping patient states, writing copy, building CRM logic, creating segments, using AI tools, QAing flows, debugging event data, launching experiments, and partnering with product, engineering, data, ops, and clinical teams to create an engine that increasingly works on its own.

• Build Legion's AI-native lifecycle engine across activation, booking, visit completion, follow-up adherence, medication renewal support, retention, reactivation, and winback.

• Design the patient communication system across email, SMS, push, in-app, transactional reminders, AI-assisted outreach, and future owned channels.

• Map the full patient journey into clear lifecycle states, triggers, audiences, suppressions, escalation rules, personalization rules, and next-best-action logic.

• Use Legion's patient data to create highly personalized journeys based on intake status, appointment behavior, insurance status, treatment stage, follow-up cadence, renewal needs, engagement, risk of lapse, and communication preferences.

• Partner with product, engineering, and data to instrument the events, properties, data models, and workflows needed for intelligent lifecycle automation.

• Build AI-assisted communication workflows that can draft, personalize, route, test, and optimize messages while staying within approved clinical, compliance, and brand guardrails.

• Create proactive flows for abandoned intake, incomplete booking, pre-visit preparation, appointment reminders, no-show prevention, post-visit follow-up, refill and renewal nudges, reactivation, churn recovery, and long-term engagement.

• Build segmentation and personalization systems that can support thousands of patient-specific journeys instead of one-size-fits-all campaigns.

• Partner with clinical operations to ensure every message reflects real care workflows, scheduling capacity, prescribing boundaries, refill policies, escalation paths, and patient support processes.

• Own lifecycle experimentation across A/B tests, holdouts, incrementality tests, send-time tests, cadence tests, channel-mix tests, AI-personalization tests, and journey-level optimization.

• Improve core funnel and retention metrics, including intake completion, booking conversion, visit completion, no-show rate, follow-up adherence, reactivation rate, churn, LTV, and patient satisfaction.

• Build the QA, approval, deliverability, consent, and compliance processes required for high-volume, AI-assisted healthcare communication.

• Ensure HIPAA, TCPA, CAN-SPAM, consent management, PHI handling, opt-outs, quiet hours, clinical accuracy, and patient trust are treated as product requirements.

• Create lifecycle dashboards and weekly reporting that show where patients are getting stuck, which journeys are working, and where AI or automation can remove manual work.

• Evaluate and operate tools such as Braze, Iterable, Customer.io, HubSpot, Klaviyo, Twilio, SendGrid, PostHog, Hightouch, Segment, RudderStack, Census, OpenAI, Claude, internal AI agents, or similar.

• Build repeatable lifecycle playbooks that can scale across states, payers, patient segments, care pathways, and future service lines.

• Build a lifecycle engine that feels less like marketing automation and more like an intelligent patient guidance system.

• Turn Legion's data into personalized, proactive communication that helps patients take the right next action.

• Meaningfully improve intake completion, booking conversion, kept visits, follow-up adherence, renewal completion, reactivation, and retention.

• Reduce manual ops work by automating the right nudges, reminders, escalations, and follow-ups before patients fall through the cracks.

• Make patients feel guided, cared for, and understood, not blasted by generic campaigns.

• Build event-triggered journeys that move real patient behavior instead of static campaign calendars that sit inside a CRM tool.

• Create AI-assisted workflows that are useful, accurate, safe, and compliant.

• Build a testing culture where lifecycle performance improves every week.

• Maintain extremely high QA standards so messages are accurate, well-timed, correctly personalized, and safe.

• Help Legion understand which patients are stuck, likely to lapse, ready to return, due for follow-up, or likely to need additional support before the problem becomes manual.

• 6+ years in lifecycle marketing, CRM, retention, engagement, growth marketing, patient engagement, consumer communications, or owned-channel marketing.

• 3+ years directly owning lifecycle programs across email, SMS, push, in-app, transactional messaging, or direct mail.

• Strong preference for experience in consumer healthcare, marketplaces, subscriptions, mobile apps, fintech, consumer services, e-commerce, or other high-volume consumer businesses.

• Experience building event-triggered journeys, segmentation systems, personalization logic, suppression rules, send calendars, experimentation roadmaps, and lifecycle reporting.

• Hands-on fluency with CRM / marketing automation platforms such as Braze, Iterable, Customer.io, Klaviyo, HubSpot, Salesforce Marketing Cloud, or similar.

• Strong AI-native operating ability. You should be excited to use LLMs, agents, data, and automation to generate better patient journeys, not just make existing workflows slightly faster.

• Strong analytical judgment: funnel analysis, cohort analysis, retention curves, A/B tests, holdouts, incrementality, attribution, LTV, churn, and reactivation.

• Comfort working with data and technical teams. You do not need to be an engineer, but you should understand events, properties, audiences, data quality, QA, and basic SQL or SQL-adjacent analysis.

• Excellent patient-facing writing judgment. You can make a message clear, warm, action-oriented, personalized, and clinically careful without sounding robotic or promotional.

• Strong product sense. You understand that lifecycle is not just marketing; it is part of the patient experience, product experience, and operations system.

• Strong operational rigor around QA, deliverability, consent, localization, link checking, dynamic content, approvals, and launch readiness.

• Healthcare judgment. You understand that messages about psychiatric care, medication, insurance, no-shows, refills, and follow-up must be handled with real care.

• Experience partnering cross-functionally with product, engineering, data, clinical operations, customer support, compliance, legal, design, and growth.

• Low ego, high ownership, and startup intensity. You can define the strategy on Monday, build the segment Tuesday, write the copy Wednesday, QA the flow Thursday, and read the results Friday.

• Bonus: experience with HIPAA, TCPA, PHI handling, patient engagement, appointment reminders, medication adherence, healthcare CRM, telehealth, LLMs, AI agents, or regulated consumer products.

• Salary: $140,000 - $260,000, based on experience

• Early-Stage Equity: Competitive

• Health Insurance: Medical, dental, and vision benefits

• Additional Perks: In-person retreats, meal stipends, lifecycle/CRM tooling budget, learning stipend, AI tooling budget

• Time Off: Flexible, unlimited vacation policy

• Work Hours: Flexible, with responsiveness around high-impact launches or patient communication issues

• Work Setup: In-Person in San Francisco, CA

• Impact: Build the AI-native communication system that helps patients access and stay in high-quality psychiatric care.

• Autonomy and Learning: Own lifecycle strategy, CRM infrastructure, patient journeys, AI-assisted personalization, experimentation, reporting, and retention systems end-to-end.

• Growth Opportunities: As Legion scales, this role can grow into Head of Lifecycle, Head of CRM, Head of Patient Engagement, or a broader growth leadership role.

• Apply here: https://jobs.ashbyhq.com/legionhealth/3a007cb1-faad-4854-a847-e4b77eaf3a42

• Overview of our hiring process:

  1. Resume + Application Screen

  2. Founder Interview

  3. Lifecycle + AI Systems Deep Dive

  4. Professional Reference Checks

• Estimated time-to-hire: 2 weeks

• Start date: ASAP

• Hiring manager: Arthur MacWaters

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.