How to Re-Engage your Audience with Win-Back Emails

How to re-engage your audience with win-back emailsIn 2020, about 30% of email marketers named audience segmentation as the top way to improve email engagement. Subscribers want your emails, so it’s up to you and your team to always be courting. When you stop surprising your subscribers and they receive the same message or a less targeted message, they might fall into the shadows of your subscriber list, becoming stagnant.

Creating a win-back email can help remind your subscribers why they signed up in the first place. Think of your subscribers as people rather than numbers to create personalized messages that speak to them.


Put yourself in your audience’s shoes

When I worked in tech customer service (a job that later led to my first steps into the email world), we offered live chat as an option to communicate between clients and the service team.

Learning to effectively speak with clients, answer their questions, and help them through chat led me to understand what it’s like to be on both sides of that chat: as a customer and as a customer support rep. That positively affected my interactions when I’d contact other companies through live chat because I felt more empathetic knowing both sides of the coin.

The same goes for how you interact with your subscribers and your customers. Placing yourself in their shoes will help you brainstorm the answers to questions like why do you stop engaging with a company’s emails? Is it the product? Design? The content?

Think about why you would stop opening emails or buying products from a company you were once a fan of, and apply that to your win-back email strategy.


Use storytelling as an email tool

Tejas Pitkar shared his take on targeting active vs. inactive subscribers, stating that you should continue interacting with subscribers until they opt out rather than cleaning inactive, opted-in subscribers. To interact with these subscribers, you need to do something different. Surprise them.

Send them a message they’re not expecting that they can appreciate, like an anniversary email (On this day, you created your profile and made these memories with us...). Pull in a collection of images with items they’ve purchased. Add testimonials to further show the value in this subscriber returning as a customer.

Tell your customer’s story, or share someone else’s story through touching photos and email copy that puts you right in the heart of that moment (this is a great option for nonprofits). Moving past the marketing and sales copy can help you connect with your audience on a personal level.


Take a step back from your work

Sometimes we get so close to our own work that we think, everything’s working as it should and we’ve set up an automation for every scenario...why aren’t more people engaging with our content? 

I recommend starting with a self-audit. Take a step back from the campaigns and compare engagement reports from the last 6-12 months.

Engagement reports will look different for everyone. This could include:

  • Unique opens
  • Unique clicks
  • Conversions
  • Donations, for nonprofits
  • Time spent on the website after clicking a link in the email

If you work for a company, ask your team to give you feedback on recent email template designs and verbiage. If you’re a freelancer or a business owner, ask a fellow email geek to review your strategy with you. Having another set of eyes can help give you a fresh perspective on what’s working, and what actions you need to take to re-engage your subscribers.


Optimize your emails for your audience

Jeanne Jennings, Founder and Chief Strategist at Email Optimization Shop, emphasized that when you’re trying to re-engage subscribers, you don’t have to act worried and ask them, “Are you okay? Is there anything we can do?” Instead, speak to your audience like humans.

You’ve heard the term “send the right message to the right people at the right time.” Before you roll your eyes - because we’ve all heard it so many times! - let’s break down how that can apply to your win-back emails.

  1. Send the right message: Write smart, concise, relatable, and personalized email copy that will resonate with your specific subscribers. Stay away from generic content, like that text you get around the holidays from someone who doesn’t know you very well. (For example: “I hope you made some great memories with your loved ones!”)
  2. To the right people: Segment your list according to customer actions, such as last purchase date, the last item purchased, last opened email, last click, or last login.
  3. At the right time: Pinpoint what time of day and what day(s) your subscribers are most engaged with your emails. Also, be punctual. If there’s something going on in the email world or in the geographical world where it’s suddenly not a good time to send any type of message, pause the campaign, and send it at a better time.

On sending your message to the right people, there are companies who have good intentions but send the right message at the right time to the wrong people.

For example: “Sorry to see you go! Is there anything we can do to win back your business and stay with us?” Sending an email like this to a happy customer who pays a monthly subscription fee, but doesn’t regularly interact with the product doesn’t sit well with the customer (I’ve seen this happen!). In this case, the company backtracked and apologized, explaining that message was an error due to an automated email.

Messages can make or break customer relationships, which is why it’s so important to test every automated message. 


Test, test, and test again

Your content’s ready, your design’s all set. Now it’s time to test your emails. If you have the resources, send a few test emails to your internal team so you can get their opinion on how the email sounds and how the message makes them feel as an inactive subscriber.

Would they be persuaded enough by this win-back series to return to your store and buy a new pair of shoes? If not, what can you do to get closer to that goal?

Always test your campaigns. Once you’ve set up your win-back email(s), don’t set it and forget it. Instead, set it and test it at least once a month to make sure everything’s running smoothly with your triggered campaigns.



Kelly Lamano is the founder and creative director of Sunshine Media Marketing in Orlando, FL. She works with businesses to tell their stories through content writing, copy editing, photography, and email marketing.
Kelly is certified in email design, SMS marketing, Google Analytics, print, broadcast, and online media. Her work has appeared in Really Good Emails, Speaking Your Brand, and Braintrust. You can find her writing content for the RGE blog and reviewing emails on Feedback Friday.
In 2018, she founded Orlando Freelancers Union SPARK where she hosted workshops for freelancers and small business owners. In 2020, she went on to co-found and organize The Freelancers Conference. This international virtual conference welcomed more than 1,300 attendees from 24 countries.


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