Lead of Retention

About the Role
As our Lead of Retention, you will own retention performance across our portfolio of DTC e-commerce brands, turning customer behavior, lifecycle data, and subscription insights into strategies that increase customer lifetime value, reduce churn, and drive repeat and recurring revenue.
This is a highly hands-on role with ownership across email, SMS, subscriptions, rebills, winback, and reactivation. You’ll also lead the transition of our retention operation from an external agency to an in-house model, building a scalable, measurable retention engine while partnering closely with Creative, CRO, Media Buying, Customer Experience, and Payments.

What You’ll Own

Own retention performance across our portfolio of DTC brands, with clear accountability for LTV, churn, repeat purchase, subscription retention, and recurring revenue.

Lead the transition of our email and SMS operation from an external agency to an in-house model, maintaining performance and revenue throughout the transition.

Own and continuously optimize email and SMS across the customer lifecycle, including flows, campaigns, segmentation, testing, and performance optimization.

Ensure lifecycle flows are correctly mapped across offers and brands, continuously identifying gaps and opportunities to improve the customer journey.

Improve subscription and rebill performance, including retry strategies, soft-decline recovery, card updates, churn prevention, and overall rebill health.

Build and optimize winback and reactivation programs using cohort analysis and incremental performance measurement.

Own deliverability and list health across operators and regions, proactively identifying and resolving performance issues.

Build a structured retention experimentation roadmap across messaging, offers, timing, segmentation, lifecycle journeys, and subscription experiences.

Analyze retention performance across revenue per recipient, LTV, cohorts, and voluntary vs. involuntary churn to identify opportunities and determine what to test next.

Partner closely with Creative, CRO, Media Buying, Customer Experience, and Payments to connect retention insights with the broader customer journey.

Build scalable processes, documentation, and best practices so retention becomes a repeatable system rather than knowledge living with individual people.

What you bring

Strong hands-on experience owning retention within a high-volume DTC e-commerce business.

Experience owning email end-to-end for an e-commerce brand generating eight figures or more in annual revenue.

Strong hands-on experience across both email and SMS, including flows, campaigns, segmentation, testing, and optimization.

Real experience with subscription and rebill performance, including retry strategies, soft-decline recovery, card updates, and involuntary churn.

Deep understanding of lifecycle marketing, segmentation, deliverability, winback, reactivation, and subscription retention.

Strong analytical skills and experience working with revenue per recipient, cohort analysis, LTV, churn, and incremental performance.

Hands-on experience with Klaviyo or similar email and SMS platforms.

Experience building and optimizing flows directly, with the ability to move from strategy and hypothesis into execution.

Experience partnering cross-functionally with Creative, CRO, Media Buying, Customer Experience, and Payments teams.

A highly proactive and autonomous approach. You’re comfortable taking ownership, solving problems, and moving quickly without requiring detailed direction.

Strong communication and organizational skills, with the ability to turn performance insights into clear actions and build scalable, well-documented ways of working.