Head of Member Growth and Retention

About us 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. Benefits and Perks: Comprehensive Health, Dental, and Vision coverage for employees and their families High deductible Health Plans with Health Savings Account (HSA) options Flexible Spending Account (FSA) Equity grant participation 401(k) program Competitive vacation policy 16 weeks paid parental leave Fully remote work flexibility (within the US) At Pomelo, we are committed to hiring the best team to improve outcomes for all mothers and babies, regardless of their background. We need diverse perspectives to reflect the diversity of problems we face and the population we serve. We look to hire people from a variety of backgrounds, including but not limited to race, age, sexual orientation, gender identity and expression, national origin, religion, disability, and veteran status. Compensation The expected base salary range offered for this role is $225,000-$250,000. This role is also eligible for an annual performance bonus and equity, giving you an ownership stake in Pomelo’s mission. Actual compensation may vary based on relevant experience, skills, competencies, and certifications. Potential Fraud Warning Please be cautious of potential recruitment fraud. With the increase of remote work and digital hiring, phishing and job scams are on the rise with malicious actors impersonating real employees and sending fake job offers in an effort to collect personal or financial information. Pomelo Care will never ask you to pay a fee or download software as part of the interview process with our company. Pomelo Care will also never ask for your personal banking or other financial information until after you have signed an offer of employment and completed onboarding paperwork that is provided by our People Operations team. All official communication with Pomelo Care People Operations team will come from domain email addresses ending in @pomelocare.com. If you receive a message that seems suspicious, we encourage you to pause communication and contact us directly at careers@pomelocare.com to confirm its legitimacy. For your safety, we also recommend applying only through our official Careers page. If you believe you have been the victim of a scam or identity theft, please contact your local law enforcement agency or another trusted authority for guidance.