Head of Engagement

Level: Senior / Head

Location: San Francisco, CA | Remote

Working Hours: Full-time

About the Role: We're partnering with an early-stage health technology company making preventive, longevity-focused care accessible to everyday patients—covered by insurance. Their AI platform supports patients between clinical visits, helping them understand their risks and build healthier habits over time. They're hiring a Head of Engagement to own the most critical driver of their entire model: whether patients actually show up, day after day, and change their behavior.

What You'll Do

• Own the patient experience and the engagement engine behind it: activation in the first week, daily habit loop design, AI coach outreach logic, and long-term retention across months—not days
• Define the engagement metrics the company steers by—activation, adherence, retention—and move them
• Design the behavior-change layer: habit formation, motivation, progression, and the timing logic behind every nudge
• Own the conversational product surface patients interact with daily
• Build an experimentation system that generates learning in days rather than waiting on quarterly clinical outcomes
• Engineer engagement for durable, healthy habit change—not extraction

What Success Looks Like

• Patients build durable health habits that outlast the program
• Engagement becomes something designed and measured, not hoped for
• Activation, adherence, and retention metrics are clearly owned and consistently improving

What You Are

• Someone who has owned a retention or engagement metric on a consumer product and measurably moved it
• Fluent in behavioral science and habit formation, and able to translate it into shipped product
• Experienced in consumer product leadership, ideally with a background in free-to-play games, gamified habit apps, or similar engagement-driven products
• A rigorous experimenter: cohorts, funnels, retention curves, ship-or-kill decision-making
• Someone who knows the difference between a habit and a dark pattern—and wants to point that skill at people's health instead of their screen time



Additional Details

• Bonus background: designing for older adults or accessibility; healthcare, digital therapeutics, or regulated-product experience; conversational or messaging-based product design (SMS/RCS, chat, voice)
• Competitive salary plus meaningful equity reflecting early-stage impact
• To apply: share a note about a product experience you built that got people to come back—what you changed, and how you knew it worked