Head of Retention

Company Overview At Rosabella, we're dedicated to helping women feel their best through every chapter of their wellness journey. Inspired by a personal story, we set out to create thoughtfully formulated supplements that provide meaningful nutritional support during menopause and beyond. By combining carefully selected ingredients with a commitment to quality and transparency, we're making it easier for women to prioritize their health with products they can trust. Position Summary The Head of Retention owns everything that happens after the first purchase: subscription retention, churn reduction, win-back, lifecycle email and SMS, and loyalty. This role is responsible for turning one-time buyers into long-term customers and measurably improving lifetime value. This is a builder role. Retention is being stood up as its own dedicated function, so you'll be building the strategy, flows, and systems largely from scratch. You work directly with the Founder / CEO and have full ownership of retention strategy and execution. Key Responsibilities Subscription Retention: Own subscription churn reduction, cancellation flow optimization, and save offers. Lifecycle Marketing: Own email and SMS lifecycle campaigns, including welcome series, post-purchase, replenishment, and win-back flows. LTV & Cohort Analysis: Analyze lifetime value, repeat purchase rate, and cohort retention trends to identify what's driving or hurting retention. Win-Back & Reactivation: Build and run win-back campaigns for lapsed and canceled customers. Loyalty & Rewards: Evaluate and potentially launch a loyalty or rewards program. Segmentation & Personalization: Build customer segments and personalized lifecycle journeys based on purchase behavior. Cross-Functional Coordination: Partner with the Creative team on retention-focused content, and with Customer Service leadership on churn signals surfaced through support tickets. Reporting: Report on retention KPIs, including churn rate, LTV, and repeat purchase rate, to leadership. Qualifications Required: Experience owning retention or lifecycle marketing at a DTC subscription brand. Deep, hands-on experience with Klaviyo or a similar lifecycle marketing platform. Strong understanding of subscription mechanics, including churn, save flows, and failed-payment recovery. Analytical, data-driven approach to LTV and cohort analysis. Track record of measurably improving retention or reducing churn. Preferred: Experience in the supplement, wellness, or subscription health category. Experience with loyalty program platforms. Familiarity with SMS marketing platforms such as Postscript or Attentive. Who This Role Is Not For This is not for people who only think in terms of acquisition. This role lives entirely in the post-purchase relationship. This is not for people who need mature systems and settled processes already in place. You'll be building this function largely from the ground up. This is not for people uncomfortable owning KPIs directly and being accountable for them. This is not for people who are resistant to direct, frequent feedback or unwilling to work closely with AI tools and offshore virtual assistants. We rely heavily on both. Work Environment Fully remote position with flexible working hours. Direct access to and regular collaboration with the Founder / CEO. Fast-paced, high-ownership environment with minimal approval layers between decision and execution. Performance and outcomes are prioritized over hours worked or process. What We Value Output-Focused: We prioritize and reward results. Accountability: Team members own their decisions, mistakes, and outcomes. Thirst for Knowledge: We learn continuously from data, customers, and each other. Hiring Process Application review. Interview with recruiter. Interview with Founder / CEO. Study: a scoped retention strategy case study.