Director of Retention

Email, SMS, Direct Mail

• Fully own Klaviyo—segmentation, flows, deliverability, testing, performance reporting, optimization.
• Build and manage email + SMS campaign and flow calendars across product launches, educational campaigns, promos, and retention themes, sending 20-30 campaigns a month.
• Oversee voice memo SMS campaigns from founders and consistently test new formats that strengthen connection and loyalty.
• Partner with contractors to brief, load, QA, and deploy campaigns and be able to use AI tooling to 10x this with automated systems.
• Cook up strategy and design for direct mail campaigns.
• Ensure a high bar for brand alignment, clarity, performance, and customer relevance.

Subscription Strategy & Growth

• Own subscription retention and growth: pricing strategy, churn mitigation, personalization, win backs, plan upgrades, save strategies, and promotion tactics and manage everything in Skio.
• Drive sub attach rate without using scammy gray hat tactics for both new customer and one time to sub, dependent on product and acquisition source.
• Be obsessed with NRR and always look at this number, trying to drive over 100%.
• Work closely with the Director of Marketing to refine subscription offerings, test new retention mechanisms, and optimize onboarding.
• Use cohort analysis, predictive modeling, and customer behavior data to build long-term strategies on increasing LTV across segments.

Customer Lifecycle Architecture

• Architect personalized journeys across channels: onboarding, activation, loyalty, replenishment, reactivation, and advocacy.
• Obsess over first order to repeat purchase data, time to second purchase, and strategies to improve these metrics to best in class retention by cohort.
• Own behavioral segmentation strategies that place customers into the optimal paths at the right time.
• Own experimentation frameworks—test messages, offers, timings, and flows across lifecycle stages and for our various personas.

Analysis, Insights & Reporting

• Track LTV, LTR, CAC payback periods, retention rate, churn drivers, cohort performance, deliverability, repeat rate, subscription health, and lifecycle lift.
• Obsess over the above numbers by acquisition source and entry SKU.
• Translate insights into action for marketing, growth, CX, and product departments.
• Identify risks, trends, and opportunities and then proactively solve problems with data driven solutions.

Cross-Functional Leadership

• Partner closely with marketing + growth leadership to align lifecycle strategy to acquisition and revenue targets.
• Work with CX, web, and product teams to inform messaging, merchandising, and UX improvements.
• Manage retention initiatives from hypothesis → scoping → testing → rollout, ensuring clarity and smooth collaboration across teams.