Key takeaways:
- Personalize winback campaigns based on specific cancellation reasons rather than sending generic messages to all churned customers.
- Perfect the timing of winback emails using AI to remove guesswork and manual labor, optimizing based on reactivation success.
- Make reengagement frictionless through features like Quick Action buttons that provide passwordless access and instantly apply special offers.
There are fundamental flaws in most winback campaigns:
- Timing
- Lack of personalization
- Lack of consideration for purchase latency
- Sending the same offer to every churned customer
To name a few…
Why? Well, for so long, winback campaigns have been an arduous and terribly tricky mechanism to run. There has always been a considerable lack of data, industry standards are still outdated, and you had to rely on educated guesses to shoot for any type of success with those campaigns.
It meant that winback campaigns hadn’t seen much success until now.
Here’s the reality: your churned customers are very win-backable, especially those who churned because they had “too much product.”
Below, we’ll get into how to winback lost customers with tried and true winback strategies and the latest tools to help you fix those fundamental flaws of most winback email campaigns.
Personalization according to cancellation reasons
For a long time, brands didn’t have any data around cancellation reasons. When they finally did, it was incredibly challenging to apply that data. You could create emails tailored to those reasons, but sending those emails to the right segments involved a lot of manual workarounds.
It’s not quite the same these days. Today, you can create cancellation surveys tied to your metrics, automatically segment those inactive customers, and trigger an email with the right messaging, all within the same workflow.

Personalizing messaging according to those various cancellation reasons is rather simple from that point.
It involves cloning the email template, altering the messaging according to each cancellation segment, and slotting it into the automated workflow.
Now, as far as messaging goes, we can give you a few examples.
If your lapsed customers say they’ve canceled because they have “too much product,” they may be more enticed by an offer to swap products, pause, or skip an order, rather than canceling their subscription altogether.
A discounted price isn’t going to work for that kind of customer, but it might work for someone who canceled because their subscription was “too expensive.”
Perfect the timing of your winback emails (without the manual workload & guesswork)
There’s really only one way to take all the guesswork and manual labor out of finding the perfect timing for a winback campaign — AI.
It’s just impossible without it. There’s too much data, too much variation in customers, and too much fluctuation in buying behaviors.
AI considers all that and more while running test after test on its own to find the perfect time to send your winback emails.
The AI works by taking the time delay range set by you, the merchant, and A/B tests the time delay within that range. Then, it optimizes based on reactivation success.
If you implement a Winback Ready event metric, it’ll pass the data to Klaviyo, where it’ll trigger the winback flow with the perfect timing.
Utilize reviews in your winback emails
There’s nothing more persuasive than hearing “I love this!” from someone who’s already head over heels for your products.
Yes, your churned customers already tried a few products. They know your brands and the full customer experience they had.
But, for customers who have only gone through one or two order cycles, tried only one product, or left because they didn’t like a particular product, using reviews from existing customers could be instrumental in winning them back.

Try sprinkling a few of these into your winback emails:
- Glowing customer reviews
- User-generated content that shows brand love
- Heart-warming testimonials
- Before-and-after success stories
Utilize the right amount of customer data in the messaging
Generic winback emails are like sending the same Valentine’s card to everyone you’ve ever dated. It’s tacky, and well, it’s definitely not going to reengage customers.
That’s why you should utilize all of the customer data you have at hand to personalize your messaging.
There is a fine line here, though. You can definitely over-personalize. You’re trying to engage customers, not love bomb them.
Some of the most essential bits of customer data to use in these emails include:
- Their name
- How long they were subscribed
- Which products they subscribed to
- Purchase history
- Cancelation reasons
- How long it’s been since they left
The messaging really could be as simple as:
“We miss seeing you order {ProductName} every month!”
“For {SubscriptionLength} months, we loved being part of your routine…”
“We understand {CancellationReason} led to your decision…”
Make it as easy as possible to re-engage customers
Every extra step your ex-customers have to take to get back to you is a chance to get cold feet. Remove every possible obstacle to make it extremely easy for former customers to return.

One of the best ways to do that is by adding a Klaviyo Quick Action button within their emails. This enables passwordless and instant access to their customer portal and applies any special deals you’re offering immediately to their account.
Your subscription management platform would have to have a URL builder that crafts easy-to-use links that take them directly to the action and removes the need for them to click around their customer portal.
Add video to your winback emails
I know it’s shocking, but personalized video messages achieve 40% save rates when included in winback emails.

It doesn’t have to be a comprehensive video. Sometimes, a simple animation to a graphic can do wonders for conversion rates.
Other times, it makes complete sense to include a video tutorial on how to use a product. Or, if you want to make it more personal and heartfelt, include a video from your CEO telling the churned customer just how valuable they are as a subscriber.
Track the success of your winback efforts and reiterate
Tracking the success of your winback flows with robust reporting shows you in-depth analytics on Winbacks Triggered, Subscriptions Saved, Winback Success Rate, and more.
When you have an easy-to-read churn reporting dashboard, with predictive analysis and AI to spot the patterns, you’re more equipped when you start iterating on your winback campaigns.