How to Create a Win-Back Email Campaign

In the bag of “quick win” marketing tricks, the win-back campaign is an oldie but goodie. It’s easy, effective and it costs nothing.

If you’re unfamiliar with win-back email campaigns, the idea is to develop a series of messages that remind your former customers and dormant prospects why they may have liked you at some point in the past (or at least entertained the idea of giving you their business).

While subscription-based businesses tend to be all over this strategy, it can also be a great fit for non-subscription-based B2B companies like manufacturers, tech and service providers.

In this post, we’ll show how to create a win-back email campaign by providing the outline for a tested playbook, sharing examples and discussing some approaches we like – and some we avoid.

Note: We’re focusing on an email-driven campaign here as that’s been most effective in our experience, but if your audience is more receptive to other channels of communication, this should still be useful.

The Win-Back Email Campaign Outline

There are lots of ways you can structure your win-back campaign – and ultimately the nuances of yours should be driven by your own customer and prospect data (i.e. what offers, messaging and content tends to resonate with them the most, and how, where and when are they likely to engage with you).

That said, there are a few tried-and-tested approaches that tend to do well.

To help get you started, here’s an outline that follows the contours of campaigns that have performed for our clients.

1. The “miss you” email
For the first email in the series, the main objective is to get back on your former customer or prospect’s radar, let them know you want them back and, if possible, show them something new or cool that they’re missing out on by not being a customer. Examples of good fodder here include new products or services, new content, upcoming events or noteworthy company updates. Even if there’s nothing especially new or exciting to share, just reminding them that you’re there and ready to help can still be effective.

Win-back email - miss you

(example of a “miss you” email courtesy of

2. The incentive email
Sometimes, your former prospects and customers may need more of a nudge to re-engage with you. If your first email didn’t lead to anything (and you’ve allowed enough time for them to take action), follow up with a special offer like a percentage off their next order, free shipping, a service discount or other incentive. If you’re reluctant to dangle a financial incentive, you can also offer something like a free piece of content or a free assessment/consultation, though your contacts will probably be more moved by dollars and cents – even if it’s a nominal amount.

Incentive win-back email
(example of an incentive email courtesy of

3. The feedback request email
If a contact is unresponsive to the first two emails in your win-back campaign, let’s be honest – there’s a strong chance you’re not going to hear from them. That said, it’s reasonable to imagine that they either missed your first two/didn’t have time to check them out, or they’d be open to telling you why they’re not re-engaging with you if prompted (which would be extremely valuable insight!). The feedback request email addresses both possibilities. If they missed your first two, this is another at-bat. If they’d be willing to tell you why they haven’t engaged, this is their invitation. This email should be short and sweet. You’re essentially acknowledging it appears that your contact doesn’t need your product or service right now and asking for feedback on why they haven’t moved forward with you. Here’s a basic version of what this might look like:

Win-Back Email Example

4. The goodbye email
If it’s crickets after the first three emails, chances are slim you’ll hear from this contact anytime soon. With the goodbye email (also known as the breakup email), you have one last shot at re-engaging them before you move on and remove them from your list. Should you expect a huge response from the goodbye email? Probably not. But you might get some bites – or at least some prospects who opt-in, which are good leads to circle back to for further nurturing down the road.

Breakup email
(example of a goodbye email courtesy of

Best Practices

As you build out your win-back campaign, there are a few best practices to follow to increase your chances of success:

  • Keep your subject lines and email copy clear and succinct
  • Use familiar, human language and personalization where appropriate (these are presumably people who have engaged with you in the past; don’t send them anonymous boilerplate content)
  • Apply audience segmentation to make the messages more relevant where possible
  • Stick to one CTA per email
  • Don’t bury the lede – if you have an incentive, feature it upfront
  • Use marketing automation to add delays and behavior-based triggers to your win-back campaign for best results (and easy management)
  • Bonus points: use AI tools to optimize your send times

A Note on the Endless Win-Back Campaign

If you’ve ever canceled a subscription, you’ve likely been on the receiving end of a never-ending win-back campaign. This is where the brand drops you in the lost-customer campaign that keeps nudging you until you come back or opt-out.

My view on this is that it makes perfect sense for a lot of direct-to-consumer (D2C) brands. I’m guessing the ROI on the Netflix or Dollar Shave Club win-back emails is prettttty good. And if a small fraction of their database finds the emails annoying and unsubscribe, I have a feeling the CMO isn’t losing much sleep over it.

For smaller B2B companies that rely more on personal relationships and word of mouth, there can be more downside to hitting contacts with a never-ending cadence of emails if they’re ultimately turned off by it. In this space, we tend to avoid going past four emails.

If you do go with the endless win-back emails, at a minimum, please add some variety to the subject lines. Don’t be like some senders in my inbox that provide me with this kind of subject line poetry:

  • “Charles, renew your subscription.”
  • (a month later) “Charles, we want you back.”
  • (a month later) “Charles, renew your subscription.”
  • (a month later) “Charles, we want you back.”
  • and so on… (Yes I know I can unsubscribe – no I don’t know why I haven’t)

Ready to Launch?

As noted, the outline here is meant to show how to create a win-back email campaign and serve as a jumping-off point to help get started. A good campaign will of course be tweaked and personalized to your business and target market. And as always, measure, rinse and repeat as you go.

For a bunch more quick-win marketing tactics and ideas like this, check out our Marketing for the Time-Strapped Small Business Leader Free Download.