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8 min read October 30, 2023

10 Tips & Tricks to Win Back Churned Subscribers

Personalization. That is the key to winning back churned customers. 

The thing is, personalization isn’t as basic as it used to be. Adding the customer’s name to their email or knowing how long they’ve been a customer isn’t going to win back churned subscribers. At least, not if they’ve tuned out of your previous offers and emails. 

If you want to personalize your winback campaigns and reengage your ex-customers, you need to truly understand what made them cancel in the first place.

Here’s how you can do just that:


4 Personalization strategies to win back churned subscribers


Tip #1: Segment by cancellation reason

If a subscriber cancels due to “too much product,” and you shoot them a winback email in just 5 days, you’ll cause more frustration.


For this cohort, any winback messaging should have an increased time delay and remind them of the benefits they are now missing out on.
This is a wildly different approach than one you should take with customers that left for reasons related to cost.

RetentionEngine’s Exit Survey Analysis Provides a Detailed Look at Churn

If you don’t segment your churned customers by cancellation data, you risk pushing them even further away from your brand.


The most common data points to use include:

  • How frequently they purchased
  • How recently they purchased
  • The value of their average order
  • The total value of all their purchases
  • The products and/or services they purchase from your company
  • How long they were a customer before they defected

Tip #2: Send personalized offers based on purchase history

Using subscription SKU data passed between your Customer Portal and Klaviyo, you can deliver personalized offers on complementary products that a customer will likely be excited to purchase.

For example, if a churned subscriber previously purchased shampoo from your brand, you can offer them a newly released conditioner rather than a product in a totally different category.


Using a tool like RetentionEngine, you can pass a subscriber’s cancellation reason data directly from a cancellation survey to Klaviyo using a Subscription Canceled metric. From here, you can ensure each subscriber receives a personalized winback treatment.


Tip #3: Trigger a winback flow to former subscribers who make a one-time purchase

If a former subscriber returns on their own for a new one-time purchase, they’re clearly still interested in your brand. Depending on their initial cancellation reason, they could be swayed back into a subscription cadence.

With the enormous amount of data at your disposal and the perfect trigger for a subscription winback flow, retarget these ex-subscribers with a reminder of the benefits they could have received on their new order had they reactivated a subscription.

To create the winback flow trigger:

  1. Create a tag for all subscribers who churn.
  2. Set up an automation rule in your email marketing platform to send a winback email to previous customers who make a one-time purchase. This email should encourage them to re-subscribe with an appealing offer, such as a discount or free gift with their resubscription.
  3. Set a specific time window for the post-purchase trigger. 
  4. Use dynamic text to add layers of personalization to the winback emails. 

Tip #4: A/B test exclusive offers within your winback emails

A/B testing add-ons, discounts, free shipping, bundles, and free gifts have very clear advantages, with the main one being identifying the best offers to win back churned subscribers. 

The problem is that this has historically been a very manual, time-consuming process. This time could otherwise be spent on retention optimizations. 

AI has really changed the game here. 

First, you can cross-compare products to find the most effective offering. You can also test these offers against your entire subscriber base versus those determined to be a churn risk. 

Paired with predictive analytics, you’ll have a whole pool of data to identify and target receptive customer segments with the most compelling offers.


ExperienceEngine allows your team to A/B test the effectiveness of various promotions.


6 tips & tricks to craft winback emails that convert


Now that you have strategy dialed in, it’s time to button everything up in an engaging email with messaging that’s too good to click away from.


To do this, you’ll want to highlight the value of your product front and center and remind customers why they loved it in the first place.

Tip #1: Test messaging & iterate before mass deployment

In the same way that you should A/B test the offer itself, we recommend testing your copy first to find out what messaging resonates.

This involves using your customer segments to trial messaging, including subject lines, CTAs, the offer itself, and the levels of personalization.


Some ideas: test FOMO messaging, exclusivity, highlighting subscription value props, and more.


We love these examples from our friends at Beekeeper’s Naturals:

Tip #2: Personalize your email and SMS messaging as much as you can

Simply referencing past purchase history, subscription length, and/or empathizing with their reason cancelation reason can help win back churned subscribers.


There are a few ways to do this:

  • Use merge tags to include the first name of the disengaged customers throughout the winback email (or at least within the greeting).
  • Highlight products from within their subscription and how long they loved those products.
  • Use dynamic content to align messaging with their reason for canceling.
  • Use the data from your offer A/B testing to provide the best offers to each of your segments.
  • Mention any recently recorded customer behavior, such as a previously opened email or a cart they recently abandoned.

Tip #3: Include opportunities to engage & provide feedback

Unfortunately, you won’t always be able to win back churned subscribers. But that doesn’t mean your efforts are a total loss.


We recommend taking advantage of this final customer touchpoint to understand what your brand could have done better to retain this subscriber.


This way, even if you lose one customer, you can leverage the insights they share to help you keep the next one.


This subscription reactivation email from A Pup Above combines humor and emotion with a reactivation discount to incentivize churned customers to re-subscribe.


A Pup Above keeps it light while reinforcing the subscription value props they offer.

They also offer an opportunity to provide customer feedback and link out to social proof. Absolute 10/10!

Tip #4: Incorporate social proof into your messaging

One of the best ways to bring customers back in is with first-hand experiences from customers like themselves.


Incorporating UGC or customer testimonials in your winback flows can add that extra “oomph” to nudge these skeptical former subscribers back to re-purchase.


Our friends at Tenzo include customer reviews directly in their winback flow:

Tip #5: Lean into 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 the New Year 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.

Tip #6: Leverage big brand 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.


When’s the right time to re-engage? Leverage AI to find the perfect time for reacquisition

Optimizing the timing of your winback communication is crucial. If you reach out too early, customers may be reminded why they churned in the first place.

Wait too long, and the harder it becomes to re-engage. Your timing needs to be juuuust right.

Our new WinbackEngine feature utilizes proprietary machine learning models to take the guesswork out of winback timing by learning the most probable time to send tailored re-acquisition emails to churned subscribers ✅

What does this mean?

No more manual work on your end, and no more A/B testing on your own!

Now, you won’t have to guess at the perfect time to reach out to churned subscribers.

You’ll be able to build winback flows with full confidence, knowing that our proprietary AI has determined the best time to re-engage your churned subscribers.

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