Consumer AI Lifecycle Product and Marketing Leader (backed by Y Combinator, $5M+ ARR, $20M+ raised)

Role Logistics

• 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

The Opportunity

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.

• Responsibilities and Deliverables

• 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.

You'll Be Successful If You...

• 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.

🧰 Ideal Background and Skills

• 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.

Compensation & Benefits

• 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.

How to Apply and Hiring Process

• 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