The Anatomy of a Perfect Retention Email


On average, how much time, energy, and money do you spend on acquiring new customers? If you’re like most business owners, it’s probably too much.

Why? Because acquiring leads and prospects is good, but retaining existing customers is better (and far-too-often ignored). A lead might become a paying customer, while an existing one is paying you already.

So which one should be getting the lion’s share of your attention? Phrased like that, the answer is clear. Sadly, it’s not the reality. Our customers can quickly feel unappreciated and taken for granted if we don’t make an active effort to show them otherwise.

That’s where a retention email can be the most powerful tool in your marketing toolbox. Don’t just assume they know how much you love them.

Show them. They’ve already fallen in love with you. It’s your job to keep them that way.

A retention email is a targeted and triggered message sent to an existing customer to increase engagement, loyalty, and satisfaction. It helps bring customers back again and again.

Still sitting on the fence about retention email marketing? Think about this:

  • It can cost up to 7x more to acquire a new customer, while it’s 5x more cost-effective to retain an existing one (source).
  • The probability of selling to a new customer is 5-20%, but it’s 60-70% for an existing one (source).
  • Increasing your retention rate by only 5% can increase your profits by up to 95%, and 65% of your revenue is generated by existing customers (source).
  • It can cost 16x more to bring a new customer to the same level of an existing one (source).
  • You could reduce customer churn by 11% simply by reaching out to them (source).
  • 80% of retail professionals believe that email is their best channel for customer retention (source).
  • The likelihood of an existing customer making a second purchase in the first year is 32%, making a fifth purchase is 70%, and a tenth purchase is 83% (source).

It pays to retain. And email marketing is the best channel for retention. A proactive customer retention email strategy is just good business. Period. 


Once they sign up, subscribe, download, or purchase, you want to do everything possible to ensure they keep finding value in you, your brand, and your products.

Retention email marketing gets that done.

The Retention Email and Segmenting

But let’s make one thing very clear: “retention email” is not a single, cookie-cutter template, nor is there a single target. You can actively go after retention in many ways, many scenarios, and for many individuals.

As with all email marketing, a segmented list is going to perform better than a blast campaign. You’ll see higher open and click-through rates, lower bounce rates, and fewer unsubscriptions.

When it comes to the retention email, you could chose to segment in several different ways. Based on customer behavior and collected data – which a service provider like SmartMailcan collect for you – your email groups might include:

  1. Your Super Fans. These customers return often, buy frequently, click-through always, and can’t wait to hear more about you, your brand, and your products. Keep doing whatever you’re doing with them. Provide extra value with how-tos and tutorials, new ways to use your product or service, upselling and cross-selling recommendations, referral codes and bonuses to encourage advocacy, and special invitations or discounts to make them feel recognized and appreciated.
  2. Your Casual Fans. Look at their behavior in detail. Is there a particular page, funnel, or section that frequently sees them bounce? Do they only use or return only at certain times of the year? Ask them how you can help, but also offer solutions upfront based on the data. Give them some quick and easy wins to generate interest and get them excited.
  3. Your Lost Causes. If a customer hasn’t purchased or used in a long time, you might try one last-ditch effort to get them back. Remind them of and agitate the problem you and your brand solve. Offer support, solutions, and possibly even an incentive to return. And if all else fails, be sure to ask why they left and use that feedback to improve for the next customer.

Retention in about increasing and maintaining engagement. Inactivity is the enemy of that, so you want to go after it wherever it occurs:

  • Onboarding inactivity. If someone signs up or creates an account, and then stops, you want to nudge them along. Build some momentum. Offer tips and tricks for getting started. Walk them through it. Engage.


  • Partial inactivity. Introduce other features, uses, or accessories to help them get the most out of your product or service.
  • Complete inactivity. These are your lost causes as mentioned above. Try one final “Hail Mary” attempt to win them back.

Email marketing works best when you send the right message to the right person at the right time. To do that, you must segment your list.New call-to-action

Types of Retention Email

Retention is a big umbrella. Once you segment, you can start to identify who needs which type of customer retention email.

  1. Welcome. Stop thinking of retention as something you do down the road. It starts at the very beginning. A welcome email creates a strong, engaged relationship from first contact.
  2. Thank you. People want to be appreciated. They want to be recognized as an individual, and not just a dollar sign. A simple thank you email goes a long way to getting them back again. In fact, any post-purchase email shows them they matter beyond just the sale.
  3. Cart abandonment. With global abandonment rates hovering around 65-80%, you can scrape back a lot of lost revenue with a cart abandonment strategy. Guide them home.
  4. Reminders. Go the extra mile and send timely reminders about accounts nearing expiration, or when to replenish consumable items. Customers will appreciate the effort.
  5. Win-back. Your lost causes, or those suffering complete inactivity, can be brought back with a strategic win-back campaign. Remember, it’s far less expensive to retain than to acquire.
  6. Milestone. A milestone may be an anniversary of them becoming a customer, or giving positive feedback on their accomplishments to encourage them to keep at it. Either way, they’ll feel great about you and your brand.
  7. Report. Generating a weekly or monthly user report is a simple but effective way to increase engagement (and therefore retention).
  8. Interactive. Higher engagement = better retention. Include videos, click-to-reveal, surveys, polls, etc. Use the data to further segment or tag by behavior.
  9. Gamify. Use rewards, points, badges, competitions, leader boards, and more to get them engaged and involved.
  10. Social Proof. Show others using, downloading, and succeeding with you and your products.
  11. Feedback/Reviews. Show them how much you want to improve for them, which will increase both gratitude and loyalty. Ask for feedback. Encourage (and reward?) reviews.
  12. Appreciation. Send a quick little email for no reason at all other than to say “thanks for being a valued customer”. Kick it up a notch with a special gift.
  13. Updates. What’s new, and what’s different from the last time they visited your site?



The right message to the right person at the right time.

Retention Email Best Practices

The rules for retention emails are the same for most other email marketing:

  • Segment your email list
  • Keep it simple and straightforward, with an uncluttered design
  • Clearly note who it is from
  • Have one simple and compelling CTA
  • Personalize as much as possible
  • Try the 4 Ps (promise, paint, proof, push) or the problem-agitate-solution formula to highlight and remind them of your value and worth

Retention Email Subject Lines

The subject line is $0.80 of your dollar. Don’t end up in the trash:

  1. You’re Missing the Best Part, [Name]
  2. There’s More. So Much More.
  3. We Miss You, [Name]!
  4. How Can We Help You Get Started?
  5. Your Weekly [Product] Stats/Report
  6. $X/X% Off Your Next Order
  7. We’ve Added a New Feature You Might Like
  8. Have You Tried/Discovered [Feature] Yet?
  9. Are You Stuck?
  10. Having Trouble?
  11. Your New [Product] Account: How to Get Started
  12. Give Us Another Chance
  13. We Want Your Opinion
  14. What Do You Think of [Product]?
  15. How Many Stars Would You Give [Product]?
  16. Thanks for Being You
  17. Here’s a Little Token of Our Affection
  18. How Did It Go?
  19. Where Does It Hurt?
  20. It’s Been a While
  21. You’ve Hit a Milestone, [Name]!
  22. Check Out These User Tricks and Tips

Retention should take as much – and ideally more – of your time as acquisition. Ignore it at your peril.



Whether it’s welcome, win-back, reward, replenish, report, post-purchase, or anything in-between, we can help make it fast, easy, and automatic.


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