Keep Your Users Coming Back
With These 5 Emails

Written by Craig Morrison - Get free updates on new posts here.


If I asked you to name the last 5 products you signed up for online, off the top of your head… could you do it?

Probably not.

So if you can’t even remember the products you signed up for, are you going to remember to go back and continue using them?

No, you’re not. At least… not without a reminder.

And that’s where email comes in. Email is a simple and extremely powerful tool that is often overlooked.

It’s job? One thing. To remind people you exist.

Sure, it gets a bit more complex than that, but this is the overall goal.

“Hey… remember us? We can help you. Come back and let us show you how.”

Email sequences can get complex, but there’s no need to be afraid of them. You can still get a ton of results from sending 5 simple emails at the proper time, to the proper users.

Below I’ve outlined these 5 emails you must be sending out to your users to keep them coming back and engaging with your product.

Bonus: To save you time, I’ve condensed this post down into a simple “cheat sheet” for you to quickly reference what each email should contain and when it should be sent. Click here to download the cheatsheet.

Email 1 – The Welcome Email

The welcome email is the holy grail of all emails you send to your users. It should be sent directly after a person signs up.

This email has the best chance of being opened, read, and interacted with. Why? Because they’re expecting it.

It’s the most important email you’ll send, as it sets the “voice” of your brand in your user’s mind forever.

If this email puts a bad taste in their mouth (eyes?) there’s a good chance they won’t open or engage with anything else you send them.

This is the one you don’t want to screw up.

When someone signs up for your product, it’s like they’re throwing their arms up and shouting “I NEED HELP WITH THIS PROBLEM AND I THINK YOU CAN SOLVE IT!!”

They need a solution, and they need it now. It’s important that you prove the value of your product to these people as quickly as possible.

This is where the welcome email comes in.

What’s the purpose?

The purpose of the welcome email is to capture this enthusiasm of a person who has just signed up, and help them take immediate action that will create their first positive experience between themselves and your product.

It should give users a clear and simple action to take that isn’t overly complicated, but it a great first step into interacting with your service.

What should it say?

First, introduce yourself to the new user. When I say “yourself” I mean an actual person behind your brand.

Maybe it’s you, the CEO, the entire team, or just a customer service rep. Regardless, don’t send the welcome email from the product itself.

Who the hell feels comforted getting a message from a computer?

Second, refer to them by their first name. It feels more personable, and helps create an actual emotional connection. Avoid calling them by their username.

Third, give them a single action to take that is simple, easy, quick, and moves them in the direction of “understanding” the value you have to offer.

I can’t tell you what action this is, it depends on what you’ve built. It could be something like uploading a photo, creating their first post, adding a few friends, or even checking out some documentation or tutorials.

For example…

Toggl is an awesome time tracking service I just started using. It’s simple and easy and I love it (I don’t get paid by them).

Their welcome email is simple and quick to read. The single call to action they’ve assigned me is to go check out a tutorial on how to use Toggl effectively.

The only downside about this email is that it showed up in my inbox as being from just “info” which wasn’t very friendly.

I would suggest something like… “Alari from Toggl” as the sender name.

Email 2 – The Follow Up Email

The follow up email is your best chance at making person feel special. It should be sent about 1-2 days after a user signs up.

What’s the purpose?

Have you ever noticed when you’re eating at a restaurant, that the server always come back to check on you right after you get your food?

Why do they do that?

Because problems tend to arise right after getting your food (or signing up for a product). The longer you have to deal with those problems, the worse your experience gets.

If you get handed a bowl of cold soup and your server doesn’t come back for 20 minutes, you are PISSED by that point.

The sooner you can send your cold soup back, the sooner you can get some hot fresh delicious cheesy salty French Onion Soup (brb!).

The purpose of the follow up email is to check in and make sure everything is going ok, and offer a way to help if it’s not.

Simple as that.

What should it say?

Keep this one short, and offer a single solution to getting the help they need.

For example, offer a link to a helpful FAQ page or video tutorials.

If you’re a relatively new startup, I’d suggest reaching out and offering to schedule a quick Skype call, or simply asking them to reply to this email for help.

Not only will you make a great impression, but speaking to people directly will give you a ton of insight on what new users are struggling with.

Eric from WhenIWork reaching out to follow up with me.

Eric from WhenIWork reaching out to follow up with me.

Email 3 – The Next Step Email

The next step email is your chance to push a user to perform a key action that leads them closer to experiencing that “aha!” moment with your product. It should be sent out about 2 weeks after they sign up.

If you have the ability to track your user’s actions, you could also send this email out to only those users who haven’t completed this action yet.

What’s the purpose?

We want users coming back right? The only way to make that happen is to first get them to use your product enough times that they understand how it makes their life easier.

Most people will sign up just to check out your product (how often have you done this?). They don’t fully understand the value of it until they perform one or two actions that really drive it home.

Your job is to identify what these “actions” are, and encourage the user to perform them.

This will require a bit of research on your part, but with enough sleuthing through analytics, and user research, you’ll come across an action that all active users have performed, and all inactive users have not.

For example, Twitter discovered that all active users were following a minimum number of other users. That’s why they made it mandatory to follow a minimum number of accounts during the signup process.

What should it say?

This depends entirely on what action you’re encouraging the user to take.

Just make sure you keep the language simple and conversational… for example…

“Hey Craig, just noticed you haven’t uploaded any photos yet! If you’ve got an extra 5 minutes, can I suggest you head to your photos page and upload a photo? I promise it will make your day.”

And don’t forget to keep it to one call to action. Don’t give them a ton of choices, just pick one thing you want them to do and ask them to do it.

Eric once again giving me the "next step" to becoming an active user.

Eric once again giving me the “next step” to becoming an active user.

Email 4 – The ‘Way to Go!’ Email

This email is all about encouragement and letting the user know how proud you are of them. It should be sent out after the user has achieved a specific milestone or goal.

What’s the purpose?

Do you remember how great it felt to get that little gold star on your crappy drawing of a dog when you were in grade 1?

You knew it sucked. Your teacher knew it sucked. But man did that gold star feel good.

You brought it home, showed your parents, and admired the way it gleamed in your siblings tear filled eyes as it hung on the fridge overtop of their horse drawing.

And the next day when it was drawing time in class? You busted your ASS to draw an even better dog.

Why? Because you craved the positive reinforcement.

The same goes for your users. When they accomplish something, they need to be rewarded with a big old gold star.

Or in this case, an email that congratulates them on their progress.

This motivates your users, and creates a positive association with your product.

Simply put, it’s going to make them want to use your product more.

What should it say?

Get creative! But keep it short. And keep it on point. This isn’t an opportunity for you to plug your new app, or your social properties, or a new feature.

This email is all about your all star user. Make them feel good, like what they’ve accomplished actually matters.

Be sure to include a specific call to action (again, not just log in) that leads them back to using your product in some way.

Headspace making me feel special after 3 days.

Headspace making me feel special after 3 days.

Email 5 – The ‘Come Back!’ Email

This email is all about reminding someone you exist. It should be sent after a period of inactivity, say 2 – 4 weeks.

What’s the purpose?

Sometimes, even the most romantic of romances sizzle out and die.

When you first brought them home, you thought you couldn’t live without them. But after eating just half the box of mini pizza bagels, something new came along and they were banished to the back of the freezer.

Forgotten in a sea of frozen corn and stale leftovers.

Then late one night, after everyone has gone to bed, you get a strange email from someone by the name of “Freezer”.

You open it, and your eyes widen as your read the words…

“There’s pizza bagels in here…”

You know you planned on eating ALL of those pizza bagels, you just forgot they were in there!

A simple reminder is sometimes all a user needs to rekindle the fire with your product.

What should it say?

This is another area you can creative. I see a lot of products use the “we miss you!” approach.

It’s friendly and unassuming. It makes the person feel wanted, while also slightly guilty at the same time.

Be sure you give the person a call to action beyond just “log in”. Ask them to do something, or peak their curiosity by saying something like “check out what we’ve added”.

With Kwilia, I took it one step further by asking people “Where did you go?”. In the email I flat out asked them if there was a reason they stopped using the service, and told them to reply to the email and let me know why.

Kwilia Come Back Email

This provided me with a TON of valuable insight into why people were dropping off.

In the end, a lot of people do reply, and a lot of people head back and start using Kwilia again too.

ComeBackEmailStats

Stats for Kwilia’s “Come Back!” Email

I’d highly suggest this approach.

Let’s Recap

I hope by this point you understand the power of emailing your users. If you aren’t yet sending out emails, I’d highly suggest making the above 5 emails a priority.

To make it easier for you, I’ve created a cheatsheet for you which is a condensed version of this post that will allow you to reference what emails to send and what they should contain. You can grab that here.

I just want to say once more that keeping in constant contact with your users is extremely vital to the success of your product.

Not convinced? Here’s a quote from the Chief Product Officer at AirBnB talking about how they went from failure to a $10b valuation…

“When we started talking to our customers and seeing how they used our service it was the defining moment of success that turned the company around.”

It doesn’t get more obvious than that. Talk to your customers, learn what they want, give it to them.

Want to learn how talking to your users translates into positive user experiences? I talk exclusively about it in my new free email course, 5 Weeks to Better UX.

Go here to sign up for the free course.

5WeekBetterUX

But how hard are these emails to set up?

If you don’t have an email system in place, setting these emails up to send off at specific times can be a pain.

I highly suggest checking out a service called Intercom.io, which is a super simple way to set up all of these emails.

I’m not getting paid by Intercom, but I do use the service, and I would list it as one of the most valuable tool I use everyday.

Once you get it set up, you could have all these emails running within hours.

Cool? Cool.

Don’t forget to check out my new course.


  • Simon Ouellette

    Thanks Craig,

    It feels like Christmas in the office when you send out an email announcing new amazing content/insight like this post. This one, couldn’t be better timed. We’re just launched our first “welcome” automatic email and this post will be plastered on the office wall for the next few weeks as we grow this aspect of our business.

    Thanks again! Keep it up, we’re already looking forward to the next post! 🙂

  • How did I not find this blog before?? Great articles here.. I’ve added it to my feed monitor so I don’t miss other posts!

    Of course I agree with everything in this article since it describes a common use case for my startup. Not having a series of automated onboarding and re-engagement emails is leaving money on the table.

    • Thanks Rob! Glad you like my articles. I send a ton of extra content when you sign up for my newsletter in the footer of the page, just in case you’re interested.

  • Micah

    Good article. Good tips for businesses to follow instead of following the ‘send an email every day with something pointless in it just for the sake of emailing the client/customer’.