7 irresistible win-back emails

McKenzie Gregory


After the avalanche of holiday emails that bury inboxes, it’s natural for some subscribers to tune out. But still, it’s hard not to take it personally.

After all, you put in a ton of effort getting them on your list in the first place. And at first, they were super into you, opening and clicking everything you sent. But now, they’ve grown distant and stopped showing interest in anything you have to say.

That’s when it’s time to win them back.

Sure, you probably shouldn’t stand outside their windows blasting Peter Gabriel, but you CAN capitalize on those intense feelings of rejection by using them to fuel an incredible win-back (or re-engagement) email. The best art arises from heartbreak… right?



With a cleverly designed win-back, you’ll not only see who’s still interested in your brand – you may even generate some immediate sales! And worst case scenario, you’ll be able to clean up your email list. For inspiration, here are a few awesome ways different brands have approached the win-back email.


1. Polyvore

This is a classic example of a B2C re-engagement email from a young, lighthearted brand. For Polyvore’s audience, this emoji-driven, Messenger-style win-back was the perfect way to draw in folks who had grown disinterested by speaking their language.



2. Zillow

This example is simple, but also incredibly effective, proving that you don’t have to be a trendy retailer or put in a ton of effort to create an effective re-engagement campaign. With a simple message and singular, focused CTA, Zillow crafted the perfect win-back for their audience and goals.



3. Ticketfly

Have you ever seen a sadder looking robot? This win-back campaign from TicketFly immediately caught my attention with that GIF in the hero image and its amazing copy. If it suits your brand, don’t be afraid to get personal (and add a dose of humor) to help win back subscribers and tug on their heartstrings.



4. Grammarly

I absolutely love the framing of this one: Initially, you think, “What is this? What badge did I earn?!”

Then, you realize what’s actually happening. But with a CTA button THAT compelling (who can resist pressing a giant red button?), this is a win-back email you simply can’t ignore.




A classic template for e-commerce re-engagement, this example showcases a great formula you can use if you aren’t sure what to do with your own win-back campaign:

1. Lead with a pithy statement like, “We miss you,” “Where have you been?” or, like in this example, “Let’s catch up.”

2. Explain how you’d love to see them open your emails, visit your website, and even offer a chance to update their preferences in case you’re not hitting the right notes.

3. Offer some products, services, or news you think the recipient might be interested in – and bonus points if you can use their previous behavior (either in the inbox or on your website) to inform those choices.



6. Bonobos

I love the simplicity of this win-back campaign. Retailers tend to overdo these things, so something this simple helps signal immediately upon opening that this message is different from regular promotions.



7. SkillShare

Win-back emails can be used for more than just re-engaging inactive subscribers! If you offer any sort of subscription service, they’re also an excellent way to win back lost business.

I particularly love this example from Skillshare, which reiterates the benefits of being a Premium member and gives you a clear path for coming back into the fold.




Seen any irresistible win-backs in your own inbox recently? Share away – I'd love to (email) geek out with you!


About the Author

McKenzie Gregory

McKenzie Gregory is a senior content manager on Emma’s marketing team. A Nashville native, she can be found covering all things email on the Emma blog, debating hyphenation rules, and watching obscene amounts of Netflix without a trace of shame.

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