Director of Retention

Thirty Madison is now part of Remedy! You can read more about the acquisition here. We are excited to join forces and continue to revolutionize healthcare accessibility! 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. Comp | Perks | Benefits The base pay range for this position is $130,000 - $155,000 per year** Robust and affordable Medical, Dental, and Vision plan options Flexible time off policy **Base pay offered may vary depending on job-related knowledge, skills, and experience. An annual incentive plan and stock options may be provided as part of the compensation package, in addition to a full range of medical, financial, and/or other benefits, dependent on the position offered. What you get to do every day Patient Activation: 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 Activation Analytics and Optimization: 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 Patient Retention: 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 What you bring to the role 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 Bonus points Experience with predictive churn modeling or working alongside a Data Science team Background in subscription or recurring-revenue business models All Company policies and procedures are subject to change without notice based on business needs. This includes, but is not limited to, the locations where we hire remote, hybrid, or onsite employees. U.S. Applicants Only Don’t meet every single requirement? Studies have shown that women and people of color are less likely to apply to jobs unless they meet every single qualification. At Thirty Madison we are dedicated to building a diverse, inclusive and authentic workplace, so if you’re excited about this role but your past experience doesn’t align perfectly with every qualification in the job description, we encourage you to apply anyways. You may be just the right candidate for this or other roles. We will ensure that individuals with disabilities are provided reasonable accommodation to participate in the job application or interview process, to perform essential job functions. Contact us at View email address on click.appcast.io to request accommodation.

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