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Stay AI+Attentive SMS Playbook

Your guide to powering better subscription experiences—right from your SMS strategy.

Cecilia Wilbur avatar
Written by Cecilia Wilbur
Updated over a week ago

🔹 Overview & Objective

If you’re using Attentive for SMS, this playbook is your shortcut to making it work smarter for your subscription program. Whether you’re helping a customer skip an order, win back a canceled subscriber, or run a quick add-on campaign, we’ll show you how to do it—with clear steps, simple keyword automations, and zero need for bots.

This isn’t about reinventing your SMS strategy but enhancing it. Connecting Attentive’s powerful messaging tools with Stay AI’s quick actions will create a seamless experience for your subscribers that drives retention, boosts engagement, and keeps everything on one phone number with one clear voice.

We’ll walk you through proven use cases, setup tips, and messaging best practices so you can get started quickly and confidently scale.

🔹 What You’ll Get from This Playbook

Here’s what you’ll walk away with:

  • Clear use cases to turn SMS into a retention tool

  • Proven flows you can launch with Attentive + Stay AI

  • Messaging tips that drive clicks and conversions

  • Personalization tactics using dynamic variables

  • Guidance on setting up event triggers and journeys

  • A simpler way to boost LTV—without needing a chatbot


🔹 Use cases: What you can build

Each use case pairs a keyword flow or event-triggered journey in Attentive with a Stay AI quick action. Just copy the idea, plug it into your automation, and you’re ready to launch smarter, more personalized retention flows.


1. Subscription welcome flow

When to use it: Someone becomes a new subscriber.

Trigger: Subscription started

What to do

  • Message: “Welcome to the club! 🎉 Your first punch is in. Tap here to check your subscription and rewards.”

  • Link: Use Attentive’s {{login_link}} (magic login to Stay AI portal)

  • Try this: Include a visual of a punch card or quick intro to loyalty perks.

2. Skip order flow

When to use it: A subscriber wants to skip their next shipment.

Trigger (optional):Upcoming order(for proactive journeys)

What to do

  • Keyword: SKIP

  • Auto-reply: “No problem—we’ll skip your next order. Tap here to confirm.”

  • Link: Stay AI Skip Order quick action

  • Pro tip: Set expectations—are they skipping one order or adjusting their whole plan?

3. Product add-on campaign

When to use it: You’re launching a new product or a limited-time flavor.

Trigger: Sent as a manual or scheduled campaign to opt-in subscribers

What to do

  • Keyword: ORANGE (or any custom flavor/product name)

  • Auto-reply: “Orange Cream is here 🍊 Want to add it to your next box? Tap below.”

  • Link: Stay AI Add Item quick action

  • Reminder: Only send to customers with marketing opt-in!

4. Payment update prompt

When to use it: A subscriber’s payment fails.

Trigger: Billing attempt failed

What to do

  • Message: “Heads up—your payment didn’t go through. Tap here to update your info and avoid order delays.”

  • Link: Stay AI Update Payment quick action. note: this will be available in June!

  • Note: This flow works if you’re syncing failed payment events via Alloy or another automation tool.

5. Cancel save flow

When to use it: A subscriber texts in saying they want to cancel.

Trigger (optional):Subscription order canceled(to send a save offer)

What to do

  • Keyword: CANCEL

  • Auto-reply: “We’re sad to see you go! Tap here to manage your subscription.”

  • Link: Stay AI cancellation quick action

  • Optional follow-up: “Changed your mind? Text RESTART to pick up where you left off.”

6. Reactivation flow

When to use it: You’re re-engaging canceled or paused subscribers.

Trigger:Subscription order canceled or Subscription order paused

What to do

  • Keyword: RESTART

  • Auto-reply: “Let’s get you back in! Tap below to reactivate your subscription.”

  • Link: Stay AI reactivation quick action

  • Bonus idea: Pair it with a discount or exclusive reward to encourage conversions.


🔹 Messaging Best Practices

Writing SMS that drives action is part art, part strategy. Here are a few quick tips to help your flows convert:

  • Be direct: Say what the customer can do—and make the next step clear.

  • Keep it short: Aim for 1–2 short sentences. SMS is a skim-friendly format.

  • Use emojis (strategically): A little flair helps grab attention, especially for product drops.

  • Start with value: Lead with what’s in it for the customer (“Heads up—your exclusive flavor is here!”)

  • End with a tap: Always close with a strong CTA and clear link.

  • Test and tweak: Try different wording, order, or timing to see what resonates.

Whether you're trying to recover a churn risk or celebrate a new subscriber, small messaging tweaks can lead to big conversion gains.


🔹 Event Triggers You Can Use

Once your integration is live, Stay AI can pass a range of events to Attentive—making it easy to build targeted journeys that feel personal and timely. Here are just a few events you can tap into:

  • Subscription started

  • Order purchased

  • Billing attempt processed

  • Upcoming order

  • Subscription order canceled

  • Subscription order paused

  • Subscription order skipped

  • Billing attempt failed

  • Item out of stock

Use these events to trigger quick-action flows, segment your audience, or tailor messaging for things like winbacks, reminders, and promos.


🔹 Using Dynamic Variables in Messages

Want to personalize your texts? Attentive lets you use dynamic variables to insert customer-specific info—great for creating more relevant messages.

Some handy variables include:

  • {{firstName}}

  • {{email}}

  • {{phone}}

  • {{loginLink}} – the magic login to the Stay AI portal

  • {{nextBillingDate}}, {{orderNumber}}, {{price}}

  • {{staySubscriptions}} – the products in a subscriber's plan

Note: {{loginLink}} works in non-transactional messages only, so save it for welcome flows, promos, and customer engagement campaigns.


🔹 Haven’t Set Up Your Attentive Integration Yet?

No worries—we’ve got you. If you’re not yet connected, follow this quick setup guide to integrate Stay AI with Attentive:

It only takes a few minutes to get connected and start triggering automated flows that make managing subscriptions over SMS a breeze.

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