Director of Retention

thirtymadison

Remote, US · Remote · United States

Posted Jun 15, 2026

Other
Remote
Marketing

Job description

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 recruiting@thirtymadison.com to request accommodation.

*This employer participates in E-Verify and will provide the federal government with your I-9 Form information to confirm that you are authorized to work in the U.S.*

*Please be aware that there are fraudulent entities who are falsely claiming to be or represent Remedy in order to solicit sensitive personal information or payment. Remedy is not in any way associated with these entities or practices. The safety and integrity of those seeking employment with us is of the utmost importance and we actively work with our legal and security teams to prevent future incidents.

Remedy will never ask for sensitive information or payment when engaging with job seekers. The entities use many methods to perpetuate these scams, including but not limited to: participating in a text-only interview, using Thirty Madison’s trademarks on their correspondence, or providing you with a seemingly legitimate offer letter. If you suspect you are a victim of this scamming, we encourage you to cease further contact and report the crime to The Federal Trade Commission.