Director of Retention Strategy

Who We Are:

Stay AI helps high-growth ecommerce brands build, scale, and optimize subscription programs. We work with leading Shopify brands to drive subscriber growth, retention, and revenue through smarter lifecycle strategies.

As we scale, the biggest opportunity is going deeper with our highest-value customers—not just supporting them, but actively improving their retention performance

Our Culture:

We are dedicated to our work, but equally committed to celebrating our achievements. Collaboration is at the heart of everything we do, as we firmly believe in the power of teamwork. While we are remote-first as a company, we try to create opportunities to meet each other. That's why we organize annual offsite retreats in the beautiful setting of Park City or Mexico!

Who You Are:

We’re hiring a Director of Retention Strategy to lead and elevate how we serve our strategic customers.

This is not a traditional Customer Success leadership role. This is a retention marketing expert who will:

• Coach and up-level our Strategic CSM team

• Bring best-in-class lifecycle and subscription strategies to our customers

• Help turn Stay AI into a true retention growth partner, not just a platform

You’ll act as the in-house expert on retention marketing, working both internally (training the team) and externally (advising top brands).

What You’ll Do:

Elevate Retention Strategy Across Strategic Accounts

• Partner with top-tier ecommerce brands as a retention and lifecycle expert

• Act as a trusted advisor on:

  • Email & SMS lifecycle strategy (flows, campaigns, segmentation)

  • Subscription retention tactics (dunning, churn prevention, winbacks)

  • Offer strategy, bundling, and upsell/cross-sell mechanics

• Identify and drive improvements in LTV, retention, and subscriber growth

Build Retention Playbooks That Scale

• Define what “great” retention strategy looks like for Stay customers

• Create repeatable playbooks for:

  • Lifecycle flows

  • Subscription retention programs

  • Customer portal optimization

• Standardize how we identify and act on retention opportunities

What You’ll Bring:

• 5–7+ years in retention marketing, lifecycle marketing, or CRM

• Experience working at an ecommerce brand or retention/lifecycle agency

• Deep, hands-on experience with Klaviyo (must-have) and SMS platforms (Postscript, Attentive, etc.)

• Proven track record driving retention strategies, LTV, subscriber growth

• Strong understanding of subscription programs (dunning, churn prevention, winbacks)

• Fluent in ecommerce metrics (LTV, churn, cohort performance)

• Experience building flows, campaigns, and retention programs

• You can go from “here’s the strategy” → “here’s exactly how to execute it”

Why Join Us?:

• The opportunity to make a huge impact at a high-growth startup

• Working alongside Stayers who are fun and collaborative

• Contribute to the growth of our product as we scale quickly