Behavioral Emails That Keep Customers Coming Back (with Examples from My Inbox)

A little email marketing automation can go a long way in keeping customers happy. Image by Ben Hussman via Flickr.

Marketing doesn’t end after the conversion. In fact, that’s where it begins.

It costs 7x more to acquire a new customer on average than it does to keep an existing one. Customer retention is too important (and expensive) to overlook.

But customer retention is more than just keeping customers. It’s about making them happy, providing a great experience and giving them a reason to spread the word about your business.

As Basecamp CEO Jason Fried wrote on Inc:

If you take care of your existing customers, they will take care of your new customers.

To take care of your existing customers, you need a good product and awesome customer service. But you also need a plan for catering to prospects who don’t reach out.

And while you can’t automate everything, you can use triggered email to identify pain points and proactively address them.

That’s where behavioral marketing comes in: collecting data about user activity and personalizing your marketing efforts based on that data.

Ready to put it to work? Here are four ways you can use behavioral email to better serve your users (and better retain them, too) – with examples pulled straight from my inbox.

1. Kiss inactivity goodbye with targeted retention emails

It’s important to understand that customer inactivity comes in different flavors:

  • Initial inactivity, where a customer hasn’t completed your onboarding process
  • Partial inactivity, where a customer is only using part of your app or service
  • Complete inactivity, where a customer isn’t engaged at all

Each type of inactivity has a different cause and requires a different set of triggers to nudge customers back into action.

Initial inactivity

Onboarding is all about momentum. A user has signed up for your product — their interest is piqued. It’s important to move them to the next step as soon as possible.

Once you lose that momentum, it’s very difficult to get back because your service/product is no longer top-of-mind.

Using email to keep users moving can be a really effective way to retain new users before they churn. Look how Twitter encourages users to complete their profile. This email is sent 48 hours after signup if the user hasn’t taken action:

Twitter Retention Email-560
Click for larger image.

Partial inactivity

It’s unlikely that your business delivers value in single way. Especially if your service is complex, there may be awesome features that aren’t getting the attention they deserve – or you may simply want to show off the customizability of your product.

For example, Pinterest users can pin items, follow other users and create boards. But did you know Pinterest also has location-based boards for planning travel?

Neither did I until they emailed me about it.

Pinterest Retention Email-560
Click for full-length email.

Complete inactivity

If a customer is completely inactive, you don’t have much to lose when trying to bring them back. It doesn’t hurt to spread your feathers once more and remind prospects why they initially signed up.

In this example from Mint, they hold nothing back. A redesign, new features, new apps… there are a number of cool things that could draw a customer back in.

Emails should typically be highly focused — one call to action, one button and no distractions — but in this case, it’s okay to spread your net far and wide since you’re selling the entire product, not just one feature.

Mint retention email-560
Click for full-length email.
Action item
To track inactivity, you need an advanced analytics tool. KISSmetrics and MixPanel are great options and you might consider using Segment to plug the data into your email provider.

Once you start collecting data, look for trends in engagement and try to replicate them.

For example, try to find which actions your best customers took early in their lifecycle and drive new users the same direction.

2. Turn attention into action with transactional email

This is a totally underrated strategy for retaining customers.

Transactional emails — receipts, invoices, notifications, reports, etc. — are opened at up to 8x the rate as compared to promotional emails.

These emails aren’t usually seen as a marketing platform, but it’s free attention that few marketers take advantage of.

When a customer signs up or makes a purchase on your site, they expect to receive a few transactional emails: a monthly report, maybe an invoice. If those emails aren’t carefully designed to increase engagement with your site, it’s wasted attention.

Attention is hard to come by these days – don’t waste it!

Here are a few examples of transactional emails that do a great job of encouraging the recipients to re-engage.

The report email

Reports emails — account overviews and usage updates — are welcome in the inbox because users know these emails are informative, not promotional.

TripAdvisor sends some of the smartest report emails I’ve ever seen.

This one is a clever report that provides lots of analytics about the reviews I’ve written. It’s transactional — wink, wink  — but there are three strong calls to action to re-engage with the site.

Click for full-length email.

The notification email

“You have a new follower!”

We’ve all gotten plenty of notifications like this. They’re not generally perceived as marketing emails because they aren’t selling anything — or are they?

In the example below, notice how Medium uses transactional language framed with social proof. It’s highly personalized for me based on people I follow and have interacted with before – all while encouraging me to engage with the site.

Click for full-length email.

The account activity email

For many apps, accounts contain all kinds of interesting data and information that the user can’t see without logging in. If you’ve got a great product, use email as a catalyst to get them logged in and active. Let the product sell itself.

Google Apps sends a report like this every month whether you’re active or not. Once you click the button, you get an overview of all the services included in your membership, not just the ones you use regularly.

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Action item
Do a quick audit of your transactional emails so that you understand every possible way your customers hear from you.

If you use a third party shopping cart for example, see how you can customize your receipts or use a standalone transactional email service to send your own. Most apps allow at least some customization. Focus on utility first, then offer extras like referral codes and upsells.

3. Use “Hail Mary” emails (because they really work)

Did you know that just 25% of free trial users actually convert to paying customers? That’s an abysmally low number considering these are people who are interested enough in your product to check it out.

That’s where “Hail Mary” emails come in: last-ditch efforts to engage an inactive user or expiring free trial.

This is how Vero became a Help Scout customer. We’ve been a customer for two years so this was a really profitable email. There were two things about this email led to the conversion.

First, it reached us at just the right time. It wasn’t that we disliked the product, it was just that we didn’t have time to test it enough during the trial. The second killer element is the testimonial — it was just what we needed to hear.

Click for full-length email.

Shopify does the same thing. Notice how there are no distractions – just a bit of copy and a strong call to action.

Click for larger image.

RunKeeper sends a very direct, frank email. They acknowledge the situation then do a great job selling the benefits of a paid membership.

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Action item
As SaaS conversion expert Lincoln Murphy says, the key to converting free trials is being proactive. Use email to execute on his tips for converting more users:

  • If they don’t convert and the trial ends, make them an irresistible offer.
  • If they don’t convert, offer a downsell.
  • If they still don’t convert, continue to educate them about your solution.

4. Avoid inactivity in the first place with lifecycle emails

Lifecycle emails are like bumpers in a bowling alley. They keep the ball out of the gutter and improve the chance it’ll knock down a few pins. These emails are designed to spark very specific actions in the customer lifecycle — anything from completing a profile to adding team members.

Encouraging engagement adds value, making it the best way to avoid inactivity in the first place. It’s the most proactive guard against churn and great way to educate your customers. Here are just a few ideas for lifecycle emails (though you can check out 135 more examples here).

The milestone email

Milestone emails build on momentum by creating a positive feedback loop. Desired behavior is rewarded to encourage repetition of that behavior. Some businesses take this to an extreme with gamification (badges, awards, levels, etc.) but anyone can take advantage of milestone emails by triggering an email when a user engages.

Here’s another RunKeeper email that does a great job making the recipient feel great about using their app.

RunKeeper Milestone Email-560
Click for full-length email.

The browsing history email

Airbnb are masters of behavioral email marketing (more on that here). They gather data as users browse their site and send targeted follow up emails.

For example, if I look at listings in San Diego, I can expect a follow up email like the one below. They even take into account the price range of the listings I checked out to make sure the email is as relevant as possible.

Click for full-length email.

Browsing history shows intent. It’s just like browsing a retail store. You might pick up an item, see how it looks, feels and smells. And if the store is smart, a salesperson will offer to help you. This email is like that salesperson.

The personalized recommendation email

Did you know that 70% of brands don’t personalize their emails? That’s a shame since personalized subject lines have been shown to increase open rates by as much as 22%.

Subject lines are just the tip of the iceberg. It’s easy to monitor behavior inside your app or site then personalize emails based on that data.

Spotify, for example, keeps track of the artists I listen to then sends emails like this when the artists release new music.

Click for full-length image.

I use Spotify every day but emails like this ensure that I always have something new and exciting to check out. Each time I get one of these, my reliance on (and love for) Spotify grows deeper.

Action item
Customer retention starts and ends with a great product.

Marketing can help – but at the end of the day, if a user isn’t satisfied, they will leave.

Get your product and marketing teams in the same room to talk through engagement, inactivity and retention.

Putting email to work

Hopefully the examples in this post will inspire you to take a fresh look at your customer retention process. It’s likely that behavioral and triggered email is a massive opportunity for your business.

To get the ball rolling, commit to creating, testing and automating just one retention email.

And don’t procrastinate – start today.

How do you keep your users engaged and happy? Let us know in the comments.

— Jimmy Daly

Mint retention email-560

About Jimmy Daly
Jimmy Daly is the content editor at Vero, a behavioral email tool, and the curator of Swipe File, a weekly marketing newsletter. Connect with him on Twitter at @jimmy_daly.
» More blog posts by Jimmy Daly


  1. Kathy

    This is a awesome article and a good resource.

  2. Robin

    Very cool article, thanks for all the info! All of these are great, especially the hale mary one (I did get one from a SaaS service recently, 6 month after I unsuscribed… they asked me to come back and gave me a big discount).

    I would recommend giving value from time to time without asking for anything in return to increase sympathy and build a strong relationsship with customers :) Just my 2 cents!

    • Jimmy

      “…giving value from time to time without asking for anything in return…”

      I love that!

  3. CowboyTim

    Great, just what I wanted to read. I am busy right now to come up with a nurturing email campaign for our slow prospects. Provide the prospect entertaining value that will solve their problem.

  4. Alf

    Hi Jimmy

    a great article and as you have said keeping your current customers happy is much easier than going out looking for new ones.

  5. Vincenzo

    nice :-)

  6. Financial Samurai

    Nice tips! I’ve been totally remiss at utilizing my e-mails. I always ask myself, “What’s so private about my e-mail post that I can’t publish online on Financial Samurai to get greater exposure?”

    What are the 3 things you write in your e-mail that is different from a typical blog post?



    • Jimmy

      Sam – They don’t always have to be different. If your content is good, there’s no reason it can’t be used as part of an onboarding, lifecycle or retention campaign.

      That being said, email is an opportunity for more personal communication so it’s a good idea to include “correspondence” – i.e. conversation, not content.


    This is what I was lacking in my email marketing. Nicely written in simple language to understand by mass.

  8. Joshua

    Really loved this post. Very informative. I also believe Behavior Based Email engagement is really powerful, especially when automated! Took a page of notes!

  9. Neryus

    Nice article. Just one small detail – all of this services available to send behavior emails only to subscribed clients.

    • Jimmy

      That’s true but you can also trigger campaigns from clicks in your emails. Not as effective but definitely a good option for bloggers and publishers.

  10. Mohak Jain

    Thanks for sharing it. Got very useful insights about emails. I’m doing MBA in Marketing. I’m sure blogs like this one would help me in understanding real time scenario. -)

  11. Vincent te Beek

    Hey Jimmy,

    Amazing article! I really like how you differentiate the different states of a user. I wanted to ask you a question with regards to subjects people almost won’t hesitate to click on but are a bit ‘shady’.

    Think of it like this, a password storage company just launched their new Two Factor Auth feature and send an email promoting it with the subject “Your …….. account might get compromised!” – This is still an OK one if you ask me.

    Second example, a company providing uptime status pages sends an email with “Your website is down, what should we tell your customers?” (bit too long but you get the point), in it they try and get the user which is currently in trial to setup automated messages in case his/her service actually goes down.

    What I’m trying to ask is, if the subject might not be true but is inviting the user to click on it because it might be something they cannot miss out on (if their account is hacked, they must take action, if their website is down, they also need to take action). Do you think the user receiving the email would be frustrated by it or would simply take action accordingly?

  12. Liz Froment

    Awesome tips Jimmy, you’ve got great stuff. I love the idea of using the transactional emails as a marketing opportunity.

  13. Steveharry

    Even A/B testing email campaigns can retain existing customers by personalizing it. Also the young conversion strategist says that even doing paid advertising can make you to retain existing customers

  14. chaten patel

    Mental!! Real Insights with great takeaway value..

  15. Irving

    I learn a lot from subscribing into Amazon Email list. Amazon is having some great minded people

  16. Mitzi

    Customers also looking for coupons and that is reason Groupon has biggest email list.

  17. Jack will

    Hi Dear,

    I love email marketing because this is best way of marketing , we can promote our product , blog post , affiliate product by this method and a newbie can also make money though it.
    so here you have shared this fantastic guide to start with email marketing.

    thanks a lot :)

  18. Shah

    I think in 4 main pillars of online marketing, one is email marketing. Email marketing is one of the best tool for re-targeting customers.

  19. Fowlere

    To be honest,I really want to use email marking to my business,because the seo for a brandnew website is very hard,but I don’t know what to start when use email marketing.of course you tips is very good,maybe I will try it.

  20. Deangelo

    Thanks for showing these examples as it can improve my conversation.

  21. Hoger

    Thanks for your tips as this will be helping me to increase traffic because seo for my website will take much time.