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
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”
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
Top Skills
What We Do
Stay AI is the subscription management app that helps DTC brands on Shopify supercharge their growth. Elevate your subscription programs with innovative, new-to-market features to optimize for LTV and reduce churn with Stay. Power any time of subscription program — from trials, to dynamic bundles, to prepaid — with frictionless subscriber touch points. Boost growth and reduce churn with our proprietary ExperienceEngine, an experience builder delivering rewards and upsells with AI-powered personalization and comprehensive A/B testing. Reduce subscriber churn by 30% more than any other available solution with RetentionEngine, which delivers the most advanced passive and active churn reduction tools leveraging proprietary AI to improve outcomes. We offer seamless, white-glove migration so you can make the switch from other subscription apps with ease. Reach out for a personalized demo today, and find out why top brands like Vita Coco, Olipop, Bright Cellars, and hundreds more choose Stay
