How to Re-Engage Inactive Contacts with an Automated Win-Back Series

Did you know your email marketing account is continually rated? 

Much like your credit is monitored and scored, your email account is monitored to gauge what your score should be. The better your rating, the better your deliverability will be. 

We live in an era where brand reputation impacts revenue more than ever before. And email providers look closely at this reputation (or how people view your emails) to see just how worthy you are to show up in people’s inbox.

There are quite a few metrics that impact your score. 

Things like your unsubscribe rate, open rate, and click-through-rate just to name a few. Really though, your rating is given based on the level of engagement from your list as a whole. 

This means that inactive contacts have a big impact on your email marketing reputation and efforts. But before you run and remove all those inactive subs on your list, we have a better idea. 

Here’s how you can reignite interest, keep as many happy contacts as possible, and maintain the health of your sender account!

How to Re-Engage Inactive Contacts

Email has long held the title as the best marketing channel for gaining revenue and for building a good relationship with contacts. 

But considering the average email list is up to 70% inactive, this channel may not be working as well as it should be. As we’ve mentioned earlier, inactive contacts cut back on the overall success of your marketing campaigns both now and in the future. 

So how do we fix this? Is there a way to spark that interest again in your inactive contacts? 

Thankfully, there is. It’s called a win-back or re-engagement email series and it’s something you can easily automate with Sendlane. 

What Is A Win-Back Email Series? 

Brands today have it tough. 

We’re all trying to gain the love of customers who are constantly being wooed by competing brands for that same admiration and ultimately, the majority market share of whatever niche you’re in. 

It’s a harsh reality, but it’s the reality nonetheless. 

There are a hundred and one reasons why a contact may stop opening or clicking through your emails, but it’s likely that their love for your brand has grown a bit cold. 

Therefore, a win-back series is designed to help you reignite that flame of brand love in the hearts of your contacts so that they start to open your emails again and click through to your heart’s delight. 

While not all your inactive contacts will engage with this series, going this route is a much better option than simply doing nothing and letting list hygiene automatically scrub your list every few months. 

Besides, you worked hard to get those leads. 

Why throw all that time and effort away when you have a chance to re-engage more of the contacts you’ve earned?

How To Set Up Your Win-Back Series 

 Setting up your win-back email series is pretty easy with Sendlane. To make this work smoothly, we have to do three things: 

  1. Create a segment of your list for inactive contacts 
  2. Send a single re-engagement campaign email to that segment
  3. Create an automation funnel inside of Sendlane to finish your win-back series


So let’s go ahead and move through this to-do list.

Step 1. Segment Your List

The whole goal for segmenting your list is to identify the people who are inactive.

By segmenting them off you can then target these contacts with more specific email messaging to help re-engage their interest.

To get started, log into your Sendlane account. Then we’re gonna create the segment:

  1. Navigate to your List menu, then click on Global Segments: 
  2. Now, create a new segment for your account. Start by giving it a name, set the Match to All and choose the following options in each of the first three drop downs:
  3. Finally, for the wait time, you can choose between Months or Days and manually enter how much time you want to wait before your list starts to segment.

Pro tip: At Sendlane, we recommend using 1 to 3 months as a best practice.

If you’ve had your list for more than a year and have never run a win-back series, set this initial timeframe for 14 days and keep sending emails as you normally would so that the segmentation can start. Give yourself about a month or so of sending before you move onto the next step.

After you’ve put the list through one win-back series, you can change your settings to the 1-3 month spacing that you feel works for you.

Doing this will give you enough time to collect enough segmented contacts to target with your automated win-back series!

Step 2. Send a Single Re-Engagement Email

Within a month or so of sending emails, you will likely start to see your segmented list growing a bit.

Now is the time when you will prep to send out a single email campaign targeted to your inactive contacts.

To do this, start by creating a new campaign in your Sendlane account:

Next, you really need to focus on your email subject line. You want to grab the attention of your contacts with this so that they’re interested enough to open this one.

Here’s a few subject styles and ideas to get the ball rolling:

  • hey, VAR_FIRST_NAME did we do something wrong?
  • Should I stay or should I go?
  • Oh no! Looks like we messed up!
  • Hey, is everything okay?

You don’t have to use these, but the point here to do get people to pay attention. Obviously, you don’t want to be crude, but subject lines like these are usually enough to trigger contacts to open your email. Since, ultimately, that’s the goal for this message!

So, once you’ve decided on your subject line, go ahead and enter it into your campaign settings:

Next, you need to specify that you want to send this email to your segmented list. In the next screen, you’ll see the option to choose that segment:

Tick the box on the segment you want to target and go to the next screen where you’ll write up the copy for your email.

In this email, can do a few things:

  • You can acknowledge that it’s been a while since your contact opened one of your emails
  • Place links to recent content on your site they may have missed
  • Give them an easy way to unsubscribe if they don’t want your emails anymore
  • Leave them an incentive to stick around. Perhaps offer a special discount on something.

To get a better idea of how your copy might look, here’s an example of an engagement email from a well-known blogger in the marketing space:

You can keep your email content light and full of personality, but also make it compelling. Anyone who opens this message needs to remember the value of your messages (and being on your list), so perk up their interest and keep them coming back.

Pro tip: Throw in a freebie resource here (like Jon did) to really drive up the engagement!

Now, before you hit the send button on your re-engagement email, you should have your automation funnel in place so that this entire process becomes easier to repeat in the future.

Let’s cover that part next!

Step 3. Create Your Win-Back Series

With your segmentation and re-engagement email in place, you can start to create your win-back series. This helps you automate some of the things you’d have to manually do otherwise.

Now, the breakdown of what we’re doing here is that we want to nurture the contacts that show consistent interest in your win-back efforts and siphon off the contacts that don’t.

Keep in mind: there are a few ways that you could set this up and it all depends and your needs and how many emails you want to send before removing someone from your list completely. This is just an example, so feel free to build yours however you want!

Alright, let’s get started building the funnel that will be your automated win-back email series!

First things first, here’s a quick visual of what you’re aiming for:

As you can see here, we start the entire funnel by targeting the people who opened your initial re-engagement campaign.


Because they already showed that they’re worth saving by engaging with your first attempt to win them back. Since these contacts have already taken the first step towards re-engaging with you, we want to focus our energy on them!

So, let’s go through the win-back series creation process step-by-step:

  1. To get started, click on Automation in the left menu, and then click on Add Automation in the top right corner of the screen.
  2. You should now see an options menu with categories and our pre-built funnels. For this Automation, we are going to choose Start from scratch.
  3. Then, choose Workflow and give your automation a name like “Win-back Series.”
  4. Next, you should have a window pop up that asks, “When should this Workflow start?” For this, choose Opens a Campaign, and under Include, tick the box of the re-engagement email that you’ve just drafted and click Ok.
  5. Then, you’ll want to alternate between adding wait actions and sending emails to continue warming up your newly re-engaged contacts with proper timing so the messages don’t feel automated!
  6. After your last win-back email, add one last Wait, setting it for 24-48 hours. This gives your contacts a bit more time to open your messages. If they don’t open within that time frame, you want to tag them as “Inactive” so that you can filter them off of your list.
  7. To do that, we’re going to add a conditional split to your funnel, directing contacts along different paths based on whether they’ve been interacting with your messages. So, add an If / Else action 
  8. Next, choose the following options within the three drop downs and click Ok
  9. After your If / Else action is set correctly, the tab will say, Does the contact match the following conditions? (My conditions are met.)” and both “Yes” and “No” answers will show underneath.
  10. Under “Yes” go ahead and add the Move to list action and specify the main list you use for your active contacts. Anyone who has made it to this point has been re-engaged and is ready to re-join your regular email list!
  11. On the “No” side you’ve confirmed that these contacts are truly inactive (since they did not open the emails you sent). So, you’ll want to use the Add Tag action to further segment these contacts so you know they’re ready to be cleaned off of your list.
  12. Finally, add End This Workflow to both sides of your conditional split to finish things up.

And when it comes to building out a win-back campaign, that’s all there is to it!

It Takes Effort, But You Can Re-Engage Inactive Contacts

While is does take some time to get this all set up, building these automations into your email marketing plan not only keep your email list healthy, but they help to handle a lot of the heavy lifting for you. 

And while you could simply scrub your list of people who just don’t open your emails, considering how hard you’ve worked to get them on your list in the first place it is definitely worth the effort to try and keep them around. 

As with any relationship, it takes two to make it work. 

And since we know you love your contacts, taking some time to help build a better relationship and keep people engaged can go quite a long way to winning both the hearts and email opens that you deserve. 

Have you built any automation funnels in your Sendlane account?

If so, let us know in the comments below. We love seeing how creative you are!

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Kristen Dahlberg

Content ManagerSendlane
As a member of the Sendlane content marketing team, Kristen focuses on everything from organization to content curation and process improvement. She enjoys variety and the challenge of learning the best way to accomplish each new goal.

Outside of work, Kristen spends as much time as possible at the beach, soaking up the San Diego sunshine!