Director of Retention Strategy
Role Overview
This senior-level role involves leading retention strategy for high-value ecommerce customers by coaching a Strategic CSM team and acting as an expert advisor on lifecycle marketing. Day-to-day responsibilities include partnering with top brands to develop email/SMS strategies, subscription retention tactics, and playbooks to improve LTV and subscriber growth. The hire will have a significant impact by transforming Stay AI into a retention growth partner and scaling best practices across strategic accounts.
Perks & Benefits
The role is fully remote with a remote-first company culture that emphasizes collaboration and teamwork, including annual offsite retreats in locations like Park City or Mexico. Career growth opportunities are strong, as the position allows for making a huge impact at a high-growth startup and contributing to product scaling. While time zone expectations are not explicitly stated, typical remote tech roles often involve flexibility with some overlap for team coordination.
Full Job Description
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
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