Head of Member Growth and Retention

Pomelo Care is the leading virtual medical practice for women and children, providing care across pregnancy, postpartum, pediatrics, menopause, and perimenopause. We combine proactive, 24/7 clinical care with technology that helps us reach patients earlier, identify risks sooner, and deliver personalized care throughout their journey. Our team includes clinicians, technologists, operators, and problem-solvers working together to make high-quality care more accessible for families nationwide.

About The Role:

As the Head of Member Growth and Retention, you will serve as the primary architect and operator of our revenue engine, owning the entire member lifecycle from lead identification through long-term retention. We are looking for a leader who balances the tactical precision needed to hit monthly revenue targets with the strategic vision to re-engineer our enrollment and retention journeys.

In this role, you will collaborate across marketing, tech, and operations to unlock step-change improvements in performance and build a world-class member growth and engagement organization.

What You'll Do:

• Orchestrate the end-to-end member growth and retention strategy, aligning cross-functional roadmaps to drive step-change improvements in business performance.
• Own the P&L-defining metrics of the business, including Enrollment Rate, LTV:CAC, and Monthly Retention.
• Partner with Strategic Finance to model performance inputs and establish long-term enrollment and engagement targets.
• Architect the end-to-end member journey, identifying high-impact engagement touchpoints and implementing automated interventions to mitigate churn.
• Translate annual financial goals into rigorous monthly and weekly operational plans to ensure the business is always paced to exceed revenue targets.
• Maintain a high-fidelity feedback loop with the executive team, providing transparent reporting on KPIs, campaign performance, and revenue pacing.
• Directly oversee a multi-disciplinary team across Outreach, Lifecycle Marketing, and Marketing Operations to foster a high-performance, data-driven culture.
• Identify and diagnose performance gaps in real-time, deploying rapid-response tactics to protect in-month revenue and retention targets.
• Influence the technical roadmap for CRM and marketing automation to ensure the organization has the precision instrumentation required for scale.
• Partner with Product and Engineering to co-author roadmaps and define KRs, ensuring technical resources are prioritized against commercial impact and that teams are held accountable for moving the needle on growth and retention metrics.
• Who You Are: 12+ years of experience in Member Growth and Engagement in a regulated industry with at least 4 years in senior leadership within subscription models, operating with a P&L owner’s mindset and total bottom-line accountability.
• Experience managing a large-scale, multi-functional organization (30+ team members).
• Ability to quantify every action, treating a 1% shift in retention as a critical financial lever rather than just a marketing metric.
• Possess the technical depth to partner with Product and Engineering to architect the infrastructure your revenue engine requires.
• Ability to move fluidly between high-level strategy and granular data, diagnosing root causes quickly and doing the math to ensure goals are reachable.
• A proven leader of multi-disciplinary teams who influences cross-functional roadmaps to unlock step-change growth.
• Ability to thrive on owning a number and proactively deploy tactics to close performance gaps before they impact the quarter.
• Comfortable balancing growth-hungry urgency with a deep respect for product integrity and the long-term member experience.
• Why you should join our team
• By joining Pomelo, you will get in on the ground floor of a fast-moving, well-funded, and mission-driven startup that always puts the patient first. You will learn, grow and be challenged, and have fun with your team while doing it.
• We strive to create an environment where employees from all backgrounds are respected. We value working across disciplines, moving fast, data-driven decision making, learning, and always putting the patient first.