BREAKING Stay AI powers subscriptions for 500+ Shopify brands OLIPOP drove a 35% lift in subscriber revenue within 90 days on Stay $15.1M raised to build a retention-first subscription platform Over $150M in lost revenue saved for merchants in one year Founded 2021 by Gina Perrelli, Pierson Krass & Taylor Cawiezell BREAKING Stay AI powers subscriptions for 500+ Shopify brands OLIPOP drove a 35% lift in subscriber revenue within 90 days on Stay $15.1M raised to build a retention-first subscription platform Over $150M in lost revenue saved for merchants in one year Founded 2021 by Gina Perrelli, Pierson Krass & Taylor Cawiezell
Company Profile · Ecommerce · AI

Stay AI

The Shopify subscription platform built for retention - turning the second purchase into a growth channel, not just another invoice.

EST. 2021 NEW YORK, USA SERIES A · $15.1M ~80 EMPLOYEES 500+ MERCHANTS
Stay AI logo
THE MASTHEAD. Stay AI's wordmark, born in 2023 when the company - once called Retextion - rebranded around the machine learning that now anchors its product.
The Dispatch

A retention engine hiding inside a subscription app

What Stay AI actually does

Most subscription software was built to do one thing well: collect a recurring payment. Stay AI was built for the harder problem that starts the moment the charge goes through - keeping the customer around for the next one.

The company sells a Shopify-native platform that lets direct-to-consumer brands launch, run, and optimize subscription programs. On the surface that means a drag-and-drop customer portal, subscriber acquisition tools, and analytics dashboards. Underneath, it means machine learning that predicts who is about to cancel, automated flows that intervene before they do, and A/B testing that treats a subscription program the way a marketer treats a landing page.

It is a deliberate reframe. Stay AI's pitch to merchants is that a subscription is not a billing relationship but a performance channel - something you test, personalize, and grow.

"There were no tools in the market that allowed you to run A/B tests or market new products to subscribers."
- Gina Perrelli, Co-Founder & CEO

That gap is the origin story. Before Stay, its founders ran an ecommerce agency and watched brands scale subscription programs with tools that couldn't be steered by the people running them. The product they wished existed became the company they built.

By The Numbers

What merchants report after switching

28%
Recurring revenue lift
32%
Add-on revenue lift
28%
Churn reduction
39%
Fewer support tickets

Source: Stay AI merchant-reported figures. Individual results vary by brand and category.

The Problem

The 17% who leave right before renewal

Who its customers are, and the problem it solves

Roughly 17% of monthly subscribers cancel right around the time their next payment is due. For a brand that spent real money acquiring them, that is the single most expensive moment in the customer lifecycle - and the one legacy tools quietly ignore.

Stay AI's customers are the DTC and CPG brands living inside that math: beverage, supplement, food, and beauty companies where a subscriber's lifetime value can dwarf their first order. The platform's job is to catch subscribers in the cancellation window and give the brand a reason - and a mechanism - to keep them.

It does that with predictive churn scoring, dynamic cancellation surveys that adapt to why someone is leaving, smart dunning to recover failed payments, and win-back automation for the ones who slip away anyway.

Where subscription revenue leaks

ILLUSTRATIVE - THE CHURN WINDOW STAY AI TARGETS
Cancel near renewal
~17%
Failed payments
Dunning
Passive lapse
Winback
Recoverable w/ Stay
Target
Products & Services

The engines under the hood

A stack of named tools, each aimed at a stage of the lifecycle
Core Platform · 2021

Subscription Platform

All-in-one Shopify subscription management with a no-code, drag-and-drop customer portal, acquisition tools, and analytics.

Churn ML · 2022

RetentionEngine

Machine-learning churn tool that scores cancellation risk and runs adaptive cancel surveys. Born from the Bellwethr acquisition.

Journeys · 2023

ExperienceEngine

Journey-based promotion builder for personalized subscriber offers, gifts, and upsells - no developer time required.

Re-acquisition · 2024

WinbackEngine

Automated win-back campaigns that re-engage churned or paused subscribers before the relationship is gone for good.

AI Suite · 2024

AI Optimization

Predictive churn forecasting, smart dunning, self-optimizing surveys, and automated A/B testing across every touchpoint.

Growth · Ongoing

Boost AOV

Add-on strategies, cross-sell, and dynamic offers designed to grow average order value inside the subscription itself.

The Difference

Built by marketers, for marketers

In a crowded field - Recharge, Skio, Awtomic, Loop, Ordergroove, Smartrr - Stay AI's wedge is who it hands the controls to. Legacy platforms often route changes through developers. Stay puts A/B testing, portal design, and offer logic in the hands of the marketing and retention teams who own the numbers.

The second differentiator is the AI layer. Rather than bolting on generic automation, Stay's models were built around the specific question of churn - a focus reinforced when it acquired Bellwethr in 2022 and folded that technology into RetentionEngine.

"We want brands to treat their subscription program as a performance channel, not just a way to collect recurring payments."
- Stay AI

The business model

Stay AI is B2B SaaS. Merchants pay recurring subscription and usage fees to run their own subscription programs on the platform, which is listed in the Shopify App Store and integrates natively with Shopify checkout and data.

Where it fits in the market

It sits in the Shopify subscription-and-retention category, positioned at the retention-obsessed end - courting mid-market and larger DTC brands for whom lifetime value, not just sign-ups, is the metric that matters. Its customer roster of recognizable CPG names is itself the market signal.

The Roster

Who's running on Stay

A shelf of familiar DTC and CPG brands

More than 500 Shopify brands have migrated to the platform. A sampling of the names:

OLIPOPMagic SpoonMomofuku LemmeARMRAVita Coco CannBeekeeper's NaturalsTru Earth GhiaPromix NutritionSuper Coffee
The Cap Table

$15.1M to bet on retention

In a market addicted to acquisition spend, Stay AI raised to double down on the opposite - keeping the customers brands already have.

RoundAmountDateLead / Notable Investors
Seed / Pre-A$7.5M2022Watchfire Ventures; Nik Sharma (Sharma Brands); Adam Turner (Postscript)
Series A$8.6MJul 2023Telescope Partners; Boulder Food Group; Riverpark Ventures; Vanterra Capital
Total$15.1MDisclosed to date
The Founders

Operators before founders

Before Stay, the founding team built and bootstrapped the ecommerce agency Lunar Solar Group, scaling it from $0 to $12M in ARR in under four years and helping brands like OLIPOP and Vita Coco grow their subscription programs.

GP

Gina Perrelli

CO-FOUNDER & CEO
PK

Pierson Krass

CO-FOUNDER & PRESIDENT
TC

Taylor Cawiezell

CO-FOUNDER, INNOVATION
The Record

From agency to platform

2018

Lunar Solar Group launches

The founders build an award-winning ecommerce agency, scaling subscription programs for brands like OLIPOP and Vita Coco.

2021

Retextion is born

Frustrated by the lack of marketer-friendly subscription tools, the team launches a platform, initially named Retextion.

2022

Bellwethr acquisition

Stay acquires Bellwethr and folds its machine-learning technology into what becomes RetentionEngine.

2023

Rebrand and $15.1M

Retextion becomes Stay AI and announces $15.1M in total funding, including an $8.6M Series A led by Telescope Partners.

2024

AI feature expansion

Ships WinbackEngine and deepens AI-driven personalization, churn prediction, and automated optimization.

2025

500+ merchants

Crosses 500 migrated merchants and reports saving customers over $150M in lost subscription revenue in a year.

Watch & Listen

Demos and interviews

Product Demo

Stay AI on YouTube

Platform walkthroughs, feature demos, and retention playbooks from the Stay AI channel.

Search demos →
Founder Interview

Gina Perrelli talks retention

The CEO on rethinking subscriptions and building loyalty for CPG brands.

Watch interviews →
Marginalia

Things worth knowing

The Q&A

Frequently asked

What does Stay AI do?

It's a Shopify-native subscription and retention platform that helps DTC brands launch, scale, and optimize subscription programs with no-code tools and AI-driven churn prevention.

Who founded Stay AI?

Gina Perrelli (CEO), Pierson Krass (President), and Taylor Cawiezell founded it in 2021, after running the ecommerce agency Lunar Solar Group.

How much has it raised?

$15.1M in total, including an $8.6M Series A led by Telescope Partners announced in 2023, plus an earlier $7.5M round.

Which brands use Stay AI?

More than 500 Shopify brands, including OLIPOP, Magic Spoon, Momofuku, Lemme, ARMRA, and Vita Coco.

How is it different from other subscription apps?

It treats subscriptions as a performance channel, giving marketers no-code A/B testing, personalized offers, and AI-powered churn prediction rather than just recurring billing.

Connect

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