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.