Job Overview
Location
Remote, USA
Job Type
Full-time
Category
Marketing
Date Posted
April 3, 2026
Full Job Description
đź“‹ Description
- • As Director of Retention Strategy at Stay AI, you will serve as the in-house expert on retention marketing, directly influencing how the company supports and elevates its highest-value ecommerce customers. This role is pivotal in transforming Stay AI from a subscription platform into a strategic retention growth partner by coaching the Strategic CSM team and advising top-tier brands on lifecycle optimization.
- • You will partner with leading Shopify-based ecommerce brands as a trusted advisor on email and SMS lifecycle strategy, subscription retention tactics (including dunning, churn prevention, and winbacks), and offer strategy such as bundling and upsell/cross-sell mechanics, driving measurable improvements in LTV, retention, and subscriber growth.
- • A core responsibility is building scalable retention playbooks that define what 'great' retention strategy looks like for Stay AI customers, including standardized lifecycle flows, subscription retention programs, and customer portal optimization to ensure consistent, high-impact execution across accounts.
- • You will coach and up-level the Strategic Customer Success Manager (CSM) team by sharing best-in-class retention marketing practices, enabling them to deliver more strategic, data-driven guidance to clients and elevating the overall service quality.
- • Working remotely with a collaborative, mission-driven team, you’ll contribute to product growth by feeding real-world retention insights back into Stay AI’s platform development, helping shape features that better serve evolving customer needs.
- • In this role, you’ll develop deep expertise in retention marketing at the intersection of ecommerce and subscription economics, gaining influence as a thought leader while helping shape the future of customer retention technology for high-growth brands.
🎯 Requirements
- • 5–7+ years of hands-on experience in retention marketing, lifecycle marketing, or CRM, with a proven track record of driving LTV, subscriber growth, and retention improvements
- • Deep expertise with Klaviyo (required) and experience with SMS platforms such as Postscript, Attentive, or similar tools used in ecommerce lifecycle marketing
- • Demonstrated experience working at an ecommerce brand or a retention/lifecycle agency, with strong understanding of subscription mechanics including dunning, churn prevention, winbacks, bundling, and upsell/cross-sell strategies
🏖️ Benefits
- • Opportunity to make a significant impact at a high-growth startup shaping the future of retention technology for ecommerce brands
- • Collaborative, fun, and dedicated team culture with annual offsite retreats in locations like Park City or Mexico to foster connection and celebration
- • Ability to contribute directly to product evolution by advising on feature development based on real-world retention challenges and opportunities faced by customers
Skills & Technologies
About Stay AI, Inc.
Stay AI provides an all-in-one subscription platform for Shopify brands, helping them secure recurring revenue, prevent churn, boost average order value, and improve customer experience. They serve a variety of industries, including beauty, CBD, food and beverage, and health and wellness. Stay AI focuses on providing user-friendly, no-code tools that allow teams to customize subscription programs without needing technical expertise. Merchants who switch to Stay AI have seen a 28% increase in recurring revenue and a 28% reduction in churn. Their platform leverages AI-powered tools and machine learning to optimize subscription growth and customer retention.
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