Director of Retention

Role Description

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.

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.

Qualifications

• 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 an 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.

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.