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How to Implement Win Back Emails for Customer Retention

A win-back strategy helps you turn a one-time customer into a loyal brand advocate.

Clear messaging and communication are key to a win-back strategy, and the customer retention email is a particularly cheap and effective way to bring one-time shoppers back into the fold. 

This is because, although good communication should be practiced at each stage of the customer journey, emails can be targeted and personalized to appeal to your customers’ previous pain points and re-spark their interest.

We’ll explore the benefits of adopting win-back strategies, the tricks marketers use for success, and how to write effective retention emails that convert.

Understanding win-back strategies

Businesses pursue win-back strategies because keeping an existing or former customer is often cheaper and more efficient than acquiring a new one. Before we explain what these strategies specifically entail, let’s cover the basics and why they should be at the core of your overall business strategy:

Definition and objectives

Win-back strategies are targeted efforts by businesses to re-engage and reclaim customers who have stopped using their services or products. This means reaching out to someone who used to shop with you (but hasn’t shown recent activity) with a special offer or a message reminding them what they’re missing out on.

The key objectives include:

  • Rekindling connections — ensuring your brand is back on your former customers’ radar.
  • Offering incentives to return — such as exclusive discounts or rewards for customer loyalty.
  • Enhancing customer satisfaction rates — ensuring they have a better experience than last time around.
  • Increasing customer lifetime value — through renewed engagement and marketing strategies.
  • Understanding why the customer left — gathering knowledge on the psychology of your customers to prevent future customer churn.
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The role of win-back strategies in customer lifecycle management

Win-back strategies are critical at various stages of the customer lifecycle when indicators suggest a customer’s engagement has waned. At whatever stage they’re implemented, the aim is to reignite a customer’s interest in your brand. 

A win-back prompt is usually initiated at clearly defined moments, such as a set period of inactivity or following a subscription cancellation. A marketing automation platform like Encharge allows you to send behavior-based emails at these moments by using events (user actions) or native integrations with billing providers. These events or integrations can trigger emails. In the example flow below, when a user cancels their subscription in Chargebee, a win-back email will automatically go out:

However, a manual approach may be favored for high-value customers.

As is the case with most areas of business management, an effective win-back strategy requires strong leadership and messaging. Essentially, change must be led from the top. Sales, marketing, and customer service departments play key individual roles, but without a coherent central strategy, their efforts to win back customers risk becoming mismatched.

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Key benefits of implementing win-back strategies

Even though win-back strategies might not be the top priority for startups focused on quick growth, businesses often turn to them eventually. Imagine a company that skyrocketed to success early on but now faces challenges converting new customers from a dwindling pool of prospects. This is a problem that almost all brands will face sooner or later.

Once a business reaches this point, looking back to previous customers becomes a logical step toward sustainable, long-term growth. Plus, the benefits of win-back strategies are more far-reaching than may have first assumed. Here’s why you should consider them:

  • Reduced customer acquisition costs — simply put, it’s cheaper to win back an old customer than to find a new one.
  • Increased revenue — win-backs do improve your bottom line. Moreover, re-engaged customers can often become some of your most valuable ones.
  • Strengthened loyalty — customers who return after leaving did so because you convinced them of the value of your brand. Naturally, we don’t like making the same mistake twice.
  • Increased word-of-mouth marketing when customers are loyal, they’re more likely to recommend your products to their friends, families, and extended social circles. This is the best kind of marketing you can possibly have!
  • Enhanced brand image — win-back strategies show that you value every customer and are committed to keeping them happy. Remember, not every business makes this kind of effort, so if done right, they can make you stand out from competitors.
  • Better product feedback — returning customers can provide valuable criticisms about what they like (or don’t like) about your products and services. This empowers brands to build stronger value propositions and deliver overall better experiences.
  • Personalization opportunities — as you experiment with different kinds of win-back messages, you’ll find a formula that your target audience enjoys for higher success rates.
  • Better understanding of your target market — you’ll also uncover tips for your general marketing strategies, as the proven interests of lapsed customers often match up with the expectations of prospects.

How to implement an effective win-back strategy

Segment your audience for targeted win-back campaigns

Not all customers are the same, and they didn’t all stop shopping with you for the exact same reasons. That said, many fall into similar categories (or “segments”) that share broad characteristics that you can allude to in your messaging.

Why not try these segments for your customer retention email strategies?

  • Deal seekers — those who exclusively shopped within your budget ranges. These shoppers are probably on a tight budget, so you can entice them with your hottest exclusive deals.
  • Unhappy customers — those who left negative feedback and felt the shopping experience didn’t live up to their expectations. You can win these shoppers back by telling them what’s changed since they left. For instance, you could highlight an improved service announcement, like same-day dispatch or their money back.
  • Busy Bees those who raced to the checkout, didn’t leave feedback, and haven’t returned since. This group is hard to understand, but there’s no harm in sending a friendly reminder email that briefly lists some complementary products to the ones they bought. Worst case, they ignore you. In the best case, they love the convenience and thoughtfulness of your follow-up.

Hulu highlights some of the new shows added to the platform since the customer churned last. Potentially enticing the churned customer to sign up again.

Those are some of the most common segments you could use, but different types of businesses may target other customer groups. For instance, a fashion brand may find some customers interested in paying higher prices for sustainable materials. A classic example is Patagonia, which frequently targets the ‘eco-conscious’ in its marketing campaigns and content creation. 

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On the other hand, a non-profit would likely rethink the way it targets segments altogether. Instead, they may focus on groups like passionate activists, who may be burnt out and need motivation, or previous donors, who have supported previous campaigns but have recently stopped their contributions. 

In each case, segmentation works because it recognizes the diversity within your customer base and addresses the specific reasons why each segment may have strayed. Consider the above categories and expand them as you learn how to produce relevant content for even more segments.

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Utilize data analytics for precise targeting

Big data is the key to an effective re-engagement email. Without understanding why a customer left, your messaging risks falling on deaf ears or, worse, further alienating them from your brand.

There are three broad steps when it comes to using data to figure out customer behavior and preferences: 1) to collect it, 2) to store and compile it, and 3) to analyze it. 

The data you’re looking for include:

  • purchase history
  • browsing activity
  • feedback channels
  • customer service interactions
  • and shopping cart abandonment (although this is a far from exhaustive list).

Once you’ve identified the most relevant data sources, you’ll need to find a CRM tool capable of compiling your data and compatible with your needs. The CRM acts like a centralized hub, and most will come with algorithmic data analysis features to uncover hidden trends.

This gives business leaders an objective view of their customer demographics, which is helpful for spotting where segments exist instead of playing guesswork. It empowers you to create customer retention emails that are targeted, relevant, and most importantly, engage the people who read them.

You may want to see if your industry has any dedicated platforms. Non-profits, for example, might use nonprofit CRM software to understand which projects resonate most with certain donor segments and that integrates with their ERP software so that they can also manage all of their financial and resource data from one centralized database.

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Personalize and tailor messages to fit each segment

Hyper-personalization is a growing trend in eCommerce, and for a good reason — customers love it. If you can serve your customers exactly what they’re looking for in one snappy email, they’re likely to click on the link and make a purchase decision right away.

In terms of what you can do with personalization for emails, you can go a lot further than simply addressing the customer by name. For starters, you could write up special occasion emails to say, “Happy birthday, here’s a discount on us,” or milestone emails to celebrate how long they’ve been shopping with you.

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Imagine how much more engaging it would be if your retention email included hyper-personalized content, such as highlighting a discount on a product they previously viewed or abandoned in their cart. That method would work well for the “Deal seeker”’ segment, but your “Busy Bees” may prefer to see complementary items to the product they just bought in their email content, for example.

Pro tip: Encharge allows you to implement all of your marketing and sales data in a fully-fledged marketing automation platform that enables you to use custom objects to personalize your emails. You can use dynamic tags with custom objects data in your email message to personalize them with unique information that goes beyond person and company information. 

The importance of timing and frequency

The frequency and timing of your win-back communications can make or break their effectiveness. Bombarding customers with daily emails will likely lead to unsubscribes, while too infrequent contact risks your brand name being overlooked in their inbox.

A win-back email from Grammarly

The sweet spot often lies in weekly to bi-weekly messages, allowing your brand to stay top-of-mind without overwhelming your audience. Timing is equally critical, with one study suggesting that emails sent mid-morning during the workweek tend to have higher open rates. That’s because your brand name is front and center just as many people check their emails as they clock into work. Following this logic, you may also want to avoid sending emails on quieter days like Friday, Saturday, and Sunday.

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Learn more: How Long Should My Automated Email Sequence Be?

Craft compelling subject lines

Your subject line is the first thing a customer sees — it’s pretty much the make-or-break moment for your win-back email. Think of it as your personal ad’s headline to your customer: it should be enticing, clear, and reflective of the content inside. Use it to spark curiosity while keeping the full details inside, so they must click on it to learn more.

Remember, your goal is to stand out in a crowded inbox. Try teasing the value they’ll find inside, like a sneak peek of a new product or a hint at valuable information they’ve missed. Keep it concise but powerful, and use eye-grabbing features like emojis, capital letters, or better yet, the customer’s name.

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Read more: 6 Killer Tips to Craft Compelling and Clickable Email Subject Lines

Create a sense of urgency

Urgency encourages action. When crafting your win-back emails, include elements that compel the recipient to act immediately. This could be a limited-time offer, last-chance reminders for an exclusive deal, or an alert that a popular item is back in stock but selling fast. The longer they think about whether to buy your product or not, the likelier it is that they’ll start looking elsewhere.

The trick here is to make your offer too good and too urgent to pass up. You should also use data to create a more personalized exclusive offer for a product that a customer has already shown an interest in. 

That said, you also need to consider whether it’s appropriate for your business and which type of urgency is applicable. Businesses with high-priced products and longer customer journeys are unlikely to win back customers by creating urgency, and applying pressure could backfire and harm your brand’s image.  

A/B testing strategies for subject lines, content, and offers.

Analyzing performance: Key metrics to watch.

The ultimate target of a customer retention email is to bring customers back into the fold and encourage them to re-engage with your brand, right?

Well, A/B testing is a great method that helps achieve this. It compares two versions of an email to see which performs better. Only one variable is changed in each variation — with A being your control version and B being the test version. This way, you can pinpoint exactly what influences the success rate of your email campaigns.

When it comes to setting up your A/B tests, you may want to compare the following variables:

  • Subject lines
  • Email content
  • Offers and promotions
  • Call-to-action (CTA) buttons
  • Email sending times

To understand how each of these tests is performing, make sure to track these key metrics:

  • Open rate — Aim for 20-30% or higher. If it’s low, try tweaking your subject line for more appeal.
  • Click-through rate (CTR) — Strive for 2-5% at least. If your CTR is lagging, consider making your CTA more prominent or the offer more enticing.
  • Conversion rate — You’ll want this to be as high as possible, but even a 1-3% rate can be good. Low conversion rates might mean you need to make your deals more rewarding or relevant to that particular segment.
  • Unsubscribe rate: Keep this below 0.5%. A higher rate could indicate that your content or frequency makes your customers feel irritated or misled.

We know what you’re thinking—that’s a lot of data points to track! Admittedly, it is a monumental task in terms of time and effort, but it’s rewarding for the insights that you’ll gain.

Many businesses opt for email automation software to start testing their win-back retention emails. These tools allow you to track key stats like email open rates or call-to-action click-through rates to see which strategies are performing best.

Another option for tracking customer retention email conversions is to use dedicated analytics software on your website. Audience analytics tools offer insights into user behavior, like where visitors find your website, i.e., through search functions, offsite links, or email links. This is useful for determining how your retention email campaigns impact overall engagement.

Finally, when analyzing the performance of your retention emails, you should consider tools specific to your industry. 

This is especially true when monitoring your cost-per-acquisition rate as you consider your budget and overall business goals. For example, SaaS billing software will allow SaaS companies to track revenue and compare the success of retention emails with emails targeted at new users through both early and growth stages.

This helps to tailor analysis to a specific business’s needs and allocate future campaign budgets accordingly. 

Leveraging feedback and data for continuous improvement

An effective email retention strategy shows the customer what they want to see. The best source of insight on this front is not your company boardroom; it’s your customers themselves! In short, you must encourage feedback to create an effective engagement strategy actively.

Popular methods for feedback collection include sending out email surveys or encouraging buyers to leave reviews on your product pages. Some businesses even implement sentiment analysis tools to interpret their brand-to-customer interactions and provide a CSAT (customer satisfaction) score for each area. This makes it simple to see where tweaks are needed.

The ideal times to seek this feedback include after a product has been delivered, following a customer service interaction, or if they unsubscribe from your mailing list. These potential pain points are usually when people have the strongest (and most valuable) opinions to learn from.

Win-back emails and your overall customer retention strategy

The synergy between win-back emails and other retention tactics.

A win-back email has its place, but it works best as part of a broader strategy for customer retention. After all, those win-back prospects represent just one slice of the pie. If you can hold onto more of your customers in the first place, your overall retention rate is bound to improve.

Try complimenting your win-back marketing strategy with these engagement tactics:

Loyalty programs — Offering in-store credits for recurring purchases encourages customers to stick with your brand over the long term. They’ll feel like their hard work is wasted if they switch to a competitor before unlocking the next level.

Screenshot taken from

Referral programs — Nothing says “thank you” like a reward for spreading the word. Try offering incentives for both your existing customers and the newcomers they bring aboard. If this succeeds, you could expand it to a full affiliate program.

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Personalized UX and retargeting — Using data from past interactions, you can create customized homepages, product recommendations, and retargeting campaigns. This takes the hassle out of the shopping process, makes your site more convenient, and can be a great reminder for users who’ve abandoned their carts. 

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Deploying these retention tactics together means your shoppers, subscribers, or volunteers stay engaged no matter what industry you’re in or what stage of the customer lifecycle journey they’re at. 

And the good news? You can continue to monitor and analyze the success of these different strategies to help you allocate your budget where it is most effective by creating a marketing budget plan and leveraging your financial software for insights. 

Building a holistic customer experience to prevent churn.

As a word of caution, it’s wise not to put all of your eggs in the ‘win-back’ basket. If you can create a stellar customer journey from start to finish, then you won’t be so dependent on winning back customers anyway.

It’s crucial to think of the customer experience holistically. Everyone, regardless of their history with your company, should be welcomed in the same way. You need to put a real effort into maintaining a cohesive and recognizable brand voice with every customer segment.

Whether it’s in social media marketing, email marketing, or service interactions, make sure the terms of your pricing structures and promotional deals are always transparent. Otherwise, you risk alienating your loyal customers if the incentives of your win-back campaigns are unfairly weighted. 

Key takeaways on win-back emails

To wrap up, a win-back strategy can be a powerful tool for improving both your brand image and bottom line. 

At its core, it’s all about reinventing your brand in the eyes of your ex-customers. You won’t have many chances to do this, so you’ll need to prepare a really good sales pitch in order to pull it off. In short, the process requires three basic steps:

  1. Understand what your customer thinks — Get into the mind of why someone left your brand. What did they like or dislike? Did they encounter any unfulfilled expectations or pain points?
  2. Identify where to improve your service — Visit review sites, analyze site traffic/sales data, or ask your customers directly. No brand is perfect, so pay attention to feedback!
  3. Win customers back through effective communication — Follow the steps outlined on this page to deliver a retention email campaign that ticks all the boxes for your ex-customers.

Your biggest priority with a win-back email is to engage your customers. It requires you to condense your brand’s unique value proposition into a short headline, grab their attention with an irresistible deal, and convert them through a simple call-to-action sales button.

Win-back emails are only a small part of your overall retention strategy, but they’re perhaps the most important nut to crack — because if you win back someone’s trust in this way, it means you’ve truly perfected the art of selling. Of course, it’ll require heaps of A/B testing and analysis, but it’s possible for anyone to achieve.

It’s your golden ticket to a loyal customer base, so get out there and do it!

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