Director of Retention

As a Director of Retention focused on Activation & Retention, you will own the full patient journey from signup through long-term care continuity. You'll be the person who ensures a new patient successfully onboards, receives their first medication on time, and stays engaged with their care plan for the long haul. This is a high-ownership, high-impact role with a direct line of sight to company growth.

• Own end-to-end activation rates defined as a patient successfully completing onboarding, converting to a paid billing cycle, and receiving their first medication shipment on time
• Build, monitor and continuously optimize automated onboarding sequences across email, SMS, and in-app channels
• Identify and eliminate friction points in the activation funnel through rigorous data analysis and A/B testing
• Partner with Product, Clinical Ops, and Fulfillment to resolve cross-functional blockers that impact on-time medication delivery
• Own activation KPIs, set baselines, establish benchmarks, and report on performance weekly

• Maintain a living dashboard tracking activation cohorts, drop-off points, time-to-activation, and conversion by acquisition channel
• Conduct regular funnel audits to surface where patients are stalling and why to quantify the revenue impact of each gap
• Run structured experiments (message content, timing, channel mix, sequencing) to improve activation rates incrementally
• Develop patient segmentation frameworks to deliver more personalized activation journeys by diagnosis category, plan type, or acquisition source
• Present activation findings and recommendations to senior leadership on a regular cadence

• Own retention rate as a primary KPI, including early churn prevention, mid-tenure re-engagement, and long-term loyalty
• Design and execute multi-channel retention programs (email, SMS, push, direct mail) tailored to patient lifecycle stage
• Build churn prediction models in partnership with Data Science to identify at-risk patients before they cancel
• Develop win-back campaigns for lapsed patients; measure and optimize reactivation rates
• Leverage patient health milestones, refill cadences, and clinical signals to trigger meaningful, timely retention touchpoints
• Work closely with Patient Success and Clinical teams to align retention messaging with care quality and outcomes
• Own the full retention P&L view: understand LTV, CAC payback, and the financial impact of every retention initiative

• 5-7 years of lifecycle, CRM, or retention marketing experience ideally at a D2C, subscription, or consumer healthcare company
• Deep fluency in lifecycle metrics: activation rate, Day 7/30/90 retention, churn rate, LTV, reactivation rate
• Hands-on experience with a ESP/CRM platform (Iterable, Braze, Klaviyo, or equivalent)
• Strong analytical skills with SQL or BI tools (Looker, Mode, Amplitude, etc.) to pull your own data
• Proven track record of running A/B and multivariate tests and translating results into roadmap decisions
• Excellent cross-functional collaborator with technical and non-technical teams
• Clear communicator who can distill complex performance data into executive ready narratives

• Experience with predictive churn modeling or working alongside a Data Science team
• Background in subscription or recurring-revenue business models