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Blog/Winning Back Churned Subscribers: 11 Tips & Tricks

Winning Back Churned Subscribers: 11 Tips & Tricks

After working with hundreds of ecommerce brands, we’ve seen so many brands miss out on a massive opportunity – winning back churned subscribers.

But that experience has also helped us to illuminate with strategies truly do work. The key? Personalization.

Personalization is ultimately about putting the right offer in front of the right person, at the right time.

Applying personalization in your subscriber winback experiences can provide massive value. We won’t lie to you – this can be really complex, but it doesn’t have to be. And if you’re using Stay Ai’s deep Klaviyo integration, it can actually be a breeze.

Let’s dig in to how you can effectively win back your churned subscribers, an unlock that untapped revenue.


11 Tips to Re-Engage Churned Subscribers: Right Offer, Right Person, Right Time

The two big keys to unlocking the winback puzzle are segmentation and personalization. From a tech perspective, this ideally involves using RetentionEngine to survey cancellation-intent customers, then passing that data from Stay Ai back to Klaviyo for use in future segmentation.

Stay Ai’s integration with Klaviyo not only provides a cancellation event trigger, but also passes critical subscriber data for further detailed segmentation. Here’s a peek of what that looks like when building email flows in Klaviyo.

But on the strategy side, you need to do some careful thinking about how to segment your churned customers and the best tactics for getting them back. We’re going to break this down into 3 buckets: optimizing offer timing, delivering the right offer, and building messaging that resonates.

Winning Back Churned Subscribers: Finding the Right Time & Place to Re-Engage

Tip #1: Consider the churned subscriber’s cancellation reasons.

When you’re determining when to hit a churned subscriber with a winback offer, you need to make sure you’re meaningfully segmenting by cancellation reason. Why? Because if a subscriber cancelled due to “too much product”, and you shoot them a winback email in just 5 days, you’re only going to cause frustration. Featured: Stay Ai’s RetentionEngine

Tip #2: Work off of seasonal customer behaviors.

Consider the periods of time each year in which people crave your product offerings most. For Health & Wellness brands, a winback nudge right around New Years is perfect for helping customers to get back on track with their goals. For food & beverage brands, the right time to launch a winback campaign might be to align with fall-favorite flavors, like a Pumpkin Spice SKU. Featured: Aura Bora

Tip #3: Leverage big announcements.

If you have a new product drop coming, or a big brand announcement, that’s a great time to launch a winback flow. Send a campaign to former subscribers so they know what’s new, or highlight a big brand event or milestone to renew their interest. Featured: Covey

Tip #4: Trigger a winback flow if a former subscriber makes a one-time purchase.

You have an enormous amount of data at your disposal – and the perfect trigger for a subscription winback flow is when a cancelled subscriber places a one-time purchase. This is a clear indication that they’re still interested in your brand’s offerings. Featured: Outstanding Foods

Winning Back Churned Subscribers: Delivering the Right Offer

Tip #5: A/B Test Promotional Offers

If you plan to incorporate a discount or free gift offer, it’s smart to A/B test promotional offers before mass-deployment to identify what has the highest take rate. We recommend testing a few things: % off discount versus free gift, $ off discount versus free gift, and % off discount versus $ off discount. Featured: Obvi’s Stay Ai ExperienceEngine Promotion

Tip #6: Tailor offers based on subscriber product preferences.

Use subscription SKU data passed into Klaviyo to deliver offers on products that a customer will likely be excited to purchase. For example, if the churned customer previously purchased shampoo from your brand, send an offer for a new conditioner formulation, rather than for a SKU in a different category. Featured: Lifeboost’s Stay Ai ExperienceEngine Promotion

Tip #7: Tailor offers to account for subscribers’ cancellation reasons.

Like we mentioned when discussing winback flow timing, it’s important to consider why your customer cancelled before slinging them an offer. Example: a customer that churned due to price and wasn’t saved by a 10% off cancellation rebuttal likely won’t take you up on a 10% off winback flow discount. Featured: Harmless Harvest

Winning Back Churned Subscribers: Crafting Messaging that Resonates

Tip #8: Test messaging and iterate before mass-deployment.

We absolutely do not recommend mass emailing your churned subscribers without testing your copy first. Instead, do some testing to find out what messaging resonates, then iterate. Some ideas: test FOMO messaging, exclusivity, highlighting subscription value props, and more. Featured: Beekeeper’s Naturals

Tip #10: Personalize winback emails or SMS messages as much as you can.

Simply stated, customers love to feel seen. Simply referencing the products a customer was formerly subscribed to, how long they were subscribed for, and/or empathizing with their reason for cancelling their subscription can have massive impact. Featured: Beekeeper’s Naturals

Tip #10: Incorporate social proof into your winback messaging.

There are few times when including social proof will do you a disservice, truly. Make sure to include UGC or customer testimonials in your winback flows to add that extra “oomph” and nudge a purchase. Featured: Tenzo

Tip #11: Include opportunities to provide feedback in the winback flow.

Unfortunately, sometimes you won’t score that winback. But that doesn’t mean your efforts are a total loss. We highly recommend taking advantage of this final customer touchpoint to understand what your brand could have done better to retain this subscriber. Featured: A Pup Above


Real-World Examples: Subscription Winback Emails That Sell

A Pup Above
This subscription reactivation email combines humor and an emotional appeal with a reactivation discount to incentive churned customers to resubscribe. A Pup Above keeps it light, while reinforcing the subscription value props they offer: savings, convenience, and flexibility. They also offer an opportunity to provide feedback, and link out to social proof. Absolute 10/10!

Beekeeper’s Naturals
This first email in this series to churned subscribers reinforces the value of both the product and the subscription at a glance, plus offers an opportunity for recipients to offer feedback. Check out the 3 varying CTAs – “we need your help”, “contact us”, and “manage your subscription” – all strategically designed for engagement.

The second email in the series ups the ante, with a reactivation discount offer, more direct messaging around what churned subscribers are missing, and a call to action that emphasizes urgency.

We love the differentiation in the CTA’s here. They all link to the same option – to resubscribe – but they’re strategically paired with an offer or routine-inspiring copy to earn that customer’s click!


Looking to boost your subscription retention rate, or provide a top-tier subscriber experience? Stay Ai’s out-of-the-box tools are designed to boost your subscription revenue, while delighting your VIP customers.

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