Head of Product Growth

About Dearest Care

Navigating healthcare alone is quickly becoming a thing of the past, just as representing yourself in court would seem unthinkable today. For decades, only those with resources could confidently navigate the healthcare system, supported by private assistance to interpret plans, contact doctors, follow up on referrals, decipher bills, and ensure nothing was missed. Most people were left with automated phone trees, complex portals, and overwhelming paperwork. Dearest Care is changing that. We equip every patient with a dedicated advocate who helps them unlock and utilize the healthcare support available to them — coordinating care, removing barriers, explaining benefits, managing next steps, and providing ongoing support. We're not replacing the human relationship with software; we're building the scalable platform that enables it. Our advocates are empowered by AI tools, clinical workflows, and operational systems, helping them deliver care with speed, empathy, and consistency. Patients need advocates. Advocates need tools. Health plans need outcomes. We're engineering the infrastructure that brings all three together. We're a mission-driven, fast-paced team committed to creating a new, essential category in American healthcare. We believe that in twenty years, having a patient advocate will be standard — and we're focused on serving the people who need one most.

About the Role

Dearest Care is hiring a Growth Operator to own our activation and conversion funnel end-to-end — from the moment a prospective patient lands on our site to the moment they show up for their first advocate intro call. This is not a channel role and not a strategy role. You will own a single number — qualified patients showing to their advocate intro — and everything between the click and that call: landing pages, eligibility and intake flows, booking, reminders, show-rate operations, and the lifecycle messaging that holds it all together. You'll also own what happens after the first call: referrals, reactivation, and the conversion of today's patients into longer-term, higher-LTV relationships. You'll work directly with the founders, a performance marketing lead driving top-of-funnel demand, and a lean engineering team. That last part matters: engineering capacity is constrained, so you need to be someone who ships experiments yourself — with landing page builders, lifecycle tools, scripts, and scrappy workarounds — rather than waiting in a ticket queue. Our funnel has real, unusual complexity: Medicare eligibility verification, MBI entry, insurance-driven drop-off points, and compliance constraints. You don't need to know Medicare on day one, but you need to be the kind of person who gets into that level of detail quickly and never lets an eligibility nuance catch the team off guard again. This is a hands-on, execution-heavy role with no team to start. You'll run a high-velocity experimentation program: forming hypotheses, shipping tests weekly, reading the data yourself, and compounding wins.

What You'll Do

• Own the full activation-to-show funnel: landing page → eligibility check → intake → booking → confirmed show to advocate intro call.
• Run a weekly experimentation cadence: prioritize hypotheses, ship tests, analyze results, document learnings, and kill or scale fast.
• Build and optimize lifecycle flows (email/SMS) in Customer.io to drive bookings, reduce no-shows, and re-engage drop-offs.
• Fix the leaks: diagnose drop-off at every funnel step (eligibility entry, MBI input, booking flow, show rates) and ship targeted improvements.
• Own funnel measurement: clean event tracking, consistent step definitions, dashboards the whole company trusts, and proactive reporting so leadership is never surprised by a trend.
• Stand up a referral motion: turn happy patients into a repeatable source of new eligible patients, friends-and-family invites, and word of mouth.
• Improve retention and revenue per patient: identify and test paths from first call to long-term engagement.
• Partner tightly with performance marketing on lead quality and message-to-funnel continuity, and with operations on advocate scheduling and capacity.
• Communicate clearly and constantly: what changed, what moved, what's next.

What You Bring

• 3–7 years in growth, with direct ownership of a consumer funnel from landing page through a booked-and-showed appointment, call, or equivalent high-consideration conversion.
• A track record of moving activation, booking, or show-rate metrics that you can walk through in detail — what you tested, what worked, what failed, and why.
• Hands-on lifecycle experience: you've personally built flows in Customer.io, Braze, Iterable, or similar.
• Analytics self-sufficiency: you pull and interpret your own data (SQL, GA4, Mixpanel, Amplitude, or similar) and don't need an analyst to know what's happening.
• Scrappy shipping ability: landing page tools, no-code/low-code, light scripting or AI tools — you find a way to test without engineering.
• Extreme bias to action: fast response times, short cycle times, and visible urgency. When something breaks, you're on it in minutes, not days.
• Clear written communication and the judgment to flag problems early rather than letting them surface downstream.

Preferred: experience in Medicare, healthcare, insurance, benefits, or other trust-heavy, compliance-constrained consumer categories.

Preferred: experience marketing to older adults, caregivers, or families navigating healthcare.

Bonus: you've built a referral program or organic/word-of-mouth loop that worked.

Why Join Us

Dearest Care is building the infrastructure that makes patient advocacy accessible at scale. Historically, only the wealthy had support navigating healthcare. That's changing: new reimbursement models and AI-driven operations make high-quality human advocacy possible for all — without sacrificing the human connection that makes advocacy work. Every percentage point you add to activation or show rate is a real person who gets an advocate instead of giving up at a phone tree. Few growth roles connect the metric to the mission this directly. You'll own a critical part of the business end to end, work directly with the founders, and help define the playbook for a category-defining healthcare company.

Applicants must be based in the United States.