Should user onboarding emails always redirect back to the app?

Seems like a ‘yes’ is the only answer. Because the app is where the good stuff is. It’s where the engagement happens. It’s the promised land.

But I’m going to try and make a case for a ‘no’.

At least a ‘not always’.  

I’ve been on around 40 drip campaigns over the last few months. Each lasted anywhere between two weeks and one month. I received between three and twenty-two (that’s right, twenty-two) automated emails each. And almost every email had one primary goal—to get me back in the app.

I get the appeal of the app redirect. The ease and the opportunity of it. I know why it can make sense. As a user, though, I’m exhausted.

It’s important I tell you why.

This post is divided into two. Part one converges on the problem: most user onboarding emails are built for the product rather than the user. Why? And what are the consequences? Part two is focused on solutions. It argues that education serves user/product fit (more on this in a minute) better than action in the early stages of a user’s journey. Skip to part 2 for principles you can apply to your own user onboarding emails.

Part 1: The case for better user onboarding emails

1.1 Why is this damn button so popular?

There’s a reason an action button is front and center in user onboarding emails. They’re the best way to reach users after their first use of the product and convince them to come back.

You need to “lure [users] back to the good stuff,” Samuel Hulick writes, “and for that, there’s no place better to find them than their inbox.”

So. That quote is from an article that Samuel wrote for Help Scout in 2016, Lifecycle Emails Are Magic Pixie Dust For User Onboarding. I was a little shocked when I read it. I disagreed with it, yes, but it also didn’t sound like Samuel ‘Better Life’ Hulick one bit.  

Until I finished his post…and understood what he was trying to do with it. It was what SaaS needed back then: A case for an underutilized tool—the user onboarding lifecycle email.

A few paragraphs into the article he warns that while user onboarding emails can be a lure, it’s good practice to design them to be more. “Many companies make the mistake” he goes on to write, “of defining their lifecycle email efforts in terms of the emails themselves, rather than the relationship those emails exist to develop.”

I’m not saying it’s Samuel’s fault the button is so inescapably ubiquitous. Far from it, the one time he made a case for onboarding emails, he cautioned against abusing them. What I am saying is that the button has always been around and it’s gotten worse since onboarding emails have become mainstream.

The reason the button is so popular is the same as it’s always been: it’s a shortcut. An easy way to drive action without worrying about whether it’s meaningful or not.

In the two years since he wrote that article, Samuel’s fears have manifested along with his hopes.

2018 SaaS doesn’t need an argument to use them anymore. Instead, we need a shout to use them better.

An onboarding email is a product coming to me after I’ve spent so much time trying to find it.

And it can (ought to) do all sorts of things: Build a rapport, showcase the product, and teach me something about the problem. Even more. Share resources, deliver insight and start a conversation.

Instead, I’ve experienced it as a blunt object of force that exploits my desire for these things to get me back inside the app.

And this puts a lot of pressure on the app to be exactly what I need it to be, doesn’t it?

1.2 User/product fit

I’m grounding my case in how we’ve learned to approach in-app user onboarding flows.

Every user comes to a product with an end in mind, Samuel Hulick writes: a better life. Great user onboarding shows a user that the better life she’s after is here in the product.

A user onboarding flow works, in other words, only when it manages to lay the foundation for user/product fit.

You’ve achieved user/product fit when a user is convinced that they’re a better version of themselves because of your product.   

And this, from Kathy Sierra’s amazing book Badass: Making Users Awesome, is what it looks like:

The thing is user/product fit is never fully established in a user onboarding flow. A-ha moments show a user that a better life is possible, but only concrete results can show that it’s certain.

In short, user/product fit is a game of inches. Your user onboarding flow can win a few. Your user onboarding emails can win a few more.  

Val Geisler, an email conversion strategist who specializes in onboarding emails, (check out her onboarding email tear downs, they’re amazing) fleshes out what this means:

‘The important thing to remember is that your new customer is not yet quite convinced that they truly need your product,’ she says in a webinar for Userlist. ‘Continuing to convince them of that is an ongoing process.’

Let’s break down how a flow lays the foundation for user/product fit.

Driving action is just one of the key techniques that it brings to bear. The others are showcasing the product and, most importantly, educating users on the problem.

A stellar user onboarding flow recognizes that some users are fully aware of the problem they want your product to solve and some users aren’t. And it balances education, showcasing, and action differently to suit each need.

The idea is that, by extension, user onboarding emails have to do the same because they work together when it comes to user/product fit.

So if the how of things doesn’t separate an onboarding flow from an onboarding email campaign, what does? The truth is, I don’t see much except an enormous amount of room.

A flow can last a few minutes at most where a drip can last a month. A flow must be concise where a drip can expand on ideas. A flow can open the door to user/product fit. An email drip can take it to the next level before a user comes back to the product. It can give them more than forced reasons to come back.

1.3 Basecamp, education, and what onboarding emails have got going for them  

What user onboarding emails have got going for them are showcasing the product and driving action. But action and showcasing cannot push user/product fit by themselves. User onboarding emails need to be educative.

Take this email from Basecamp. It’s built to do one thing—get me to go back to Basecamp—and it does that really well. But it does nothing for user/product fit.

A few things that this email’s got going for it:

  • There’s a clear tie to Basecamp’s homepage. Basecamp’s homepage says ‘stop the email chaos’ and this mail tells me what feature I can use to do it.
  • The video is a fantastic showcase of what the product is capable of.
  • Most importantly, by the time I get to the button, I want to click it.

In essence, Basecamp’s email gets me to act by showcasing a feature that, if I signed up, I’m probably interested in. What it’s missing is education on the problem.

When I received this email from them, I wasn’t sure that Basecamp was the right tool for me. They could have fixed this with a little education. Why do discussion threads work better than emails? How should my team be thinking about projects to use them effectively? Is it possible I could use discussion groups and be in the same chaotic fix that I’m in right now?

Educative elements do two amazing things to push user/product fit:

  • They help a user acclimatize to the thought behind a product before they start using it.  I could have come to the discussion threads feature knowing why it’s so productive.
  • They allow a product to empathize with users. When Basecamp tells me what I’m doing wrong and why my emails are so chaotic, they’re empathizing with me. And I trust them a little more for it. Nothing pushes user/product fit better than trust.

With a slight focus on education, this email could rebalance itself, and work for user/product fit before the app comes back into the picture.

With a slight focus on education, this email could rebalance itself, and work for user/product fit before the app comes back into the picture.

This email could have driven me back a little more assured that Basecamp is the tool I’ve been looking for all along.

Part 2: Education in user onboarding emails

So far we’ve covered why the ‘back to app’ button is so popular in user onboarding emails. And what user/product fit opportunities products are missing by relying on it so much.

Education can introduce users to the thought work behind a product so they can approach it better. And it allows a product to empathize with a user’s pain and build a little trust.

This part—with three principles—is a guide on how to work educative elements into your user onboarding emails.

2.1 The approach to education

The two pillars of user onboarding—the user onboarding flow, and the user onboarding email campaign—must rely on education. Albeit a little differently from each other.  

User/product fit begins at the homepage.

When Drift’s homepage says sales and marketing is becoming more conversational, they’re educating visitors on a trend in the world. They just have to make it as catchy as possible because a landing page is a “billboard [to a user] going by at sixty miles an hour”, in Steve Krug’s words.

When Freedcamp gives users a choice of interface inside the app, they’re educating them on how to approach project management. And they’ve had to make it as succinct as possible.  

Because an onboarding flow has less of an attention constraint and more of a time constraint. The faster it gets to an aha moment the better.

In exactly the same way, user onboarding emails need to adapt education to 1) medium and 2) the context of their users.

As far as the medium goes, there are neither attention constraints nor time constraints (because a drip can be spread out over a week or two). The constraint is trust. With a homepage and a flow, I’m seeking out a product. An email is a product coming to me; a personal place—my inbox.   

As far as users go, they ’re testing out a new product—integrating it into their lives and experimenting with the fit.

Given the medium and the context, education in user onboarding emails must be shaped by how adults learn a new skill or method.

Most educators rely on Malcolm Knowles’ principles of adult learning to guide them.

Here’s how they can work for education in user onboarding emails. 

2.2 Principle #1: A user’s compelling context is her internal motivation to take the next step. And the step after that.  

When you’re playing a game, a progress bar is a great motivator. When you’re in the throes of a problem…not so much. What gets you through is how far you’re willing to go for a solution. A progress bar is an external motivator. Taking the next step because you want to—that’s internal motivation.

A progress bar can help, sure, but capitalizing on why your users are here is the best way to help them learn about your product.

Story time. I signed up for EverydayCheck, a habit tracker, two years after I started getting serious about tracking my habits.

My habit tracking journey started with a physical calendar. There was a notepad for a while (so I could take my calendar with me). I experimented with my phone’s calendar for a while. I even tried a to-do app when the calendar didn’t work out.

Then I discovered EverydayCheck and realized it could give me a calendar, a notepad, mobility, and a list all at once.  I learned that its maker, Joan Boixados, built a tool so flexible because he’d been through a similar journey tracking his habits. I loved the way he thought about the problem. Learning through his experiences got me hooked.

Kathy Sierra, again, frames this distinction between ‘problem in a user’s life’ and ‘solution to solve it’ beautifully.

‘What bigger, compelling context are you a subset of?’ she asks.

“Tools matter,” Kathy writes, “But being a master of the tool is rarely our user’s ultimate goal. Most tools (products, services) enable and support the user’s true–and more motivating–goal.”

“Nobody wants to be a tripod master. We want to use tripods to make amazing videos.”

All this to say that talking about your features or showing me a progress bar in your user onboarding emails is…fine. But pushing my understanding of the compelling context that you’re a subset of can be the biggest motivator.

Counterexample: Zendesk  

At one point in Zendesk’s email drip, Jennifer sent me a beautiful, personal mail that got me thinking about the long term.

The subject didn’t have too much to do with the email. Even so, there were some things that the email did well:

  • It let me know what Zendesk’s other customers’ priorities for the year were and that got me thinking about ours,
  • Jennifer’s reassuring line—‘I am here to help’ really put me at ease (it’s the little things that have the biggest impact),
  • It redirected to a get started guide instead of the app.

Unfortunately, it was surrounded by emails nudging me back to the app.

This was the first mail I received from Zendesk:

It came with two redirects back to the app, and links to Zendesk’s other products.

Not that I didn’t want to connect my account. The external motivation worked. 

But Jennifer’s email was much more motivating—it got me thinking about all the things that I could be building with Zendesk. And it was the only one of the kind that I received.

Most of the other emails in their drip nudged me as well. Towards other products in the suite, other features in their Support offering, and product demos.

This was one that arrived towards the end of my trial:

A knowledge base and a chat widget would help me serve my customers better, no doubt. But the timing of the push couldn’t have been worse. I was bang in the middle of trying to learn how Zendesk’s primary offering tackled my email chaos.

2.3 Principle #2: Personalize for delight but customize for learning  

Customization and personalization are used interchangeably in the development world. Mostly because they achieve the same goal—an experience tailored to the user’s interest.

There is a difference between them, though, according to Nick Babich, the editor-in-chief at UX Planet. And it’s key to crafting better emails for users who are just beginning journeys of integrating a new product into their lives.

“Personalization is done by the app being used,” Nick writes. “The App tries to deliver content, experience, or functionality that matches a user’s needs.”

But “customization is done by the user. An app/service may enable users to customize or make changes to the experience to meet their specific needs.”

You personalize lifecycle emails in two ways: either you can segment your users and send them emails tailored to in-app behavior. If they visit their profile page, for example, you follow up with an email asking them to complete the process.

Or you segment them and follow up based on how they’ve interacted with your previous emails. Users that open your first email get X-email next, for example, and users that open it and click through get Y-email.

You customize, on the other hand, with choices and options. Choices of members in your team to contact and learn from, links to resources and other educational content to grapple with the problem, and a choice of next steps (that don’t necessarily have to lead back to the app).

Personalization and customization are both important. But customizing emails will help users direct their own learning. Which is key to their learning better, according to Knowles’ theory.

Counterexample: Hotjar

To illustrate, here’s Hotjar. I received fifteen emails from Hotjar over the course of my month-long trial period.

I went to Hotjar for something specific: their visitor recording feature.

But I was put on a generic here-are-all-the-features drip anyway.

My point isn’t that this drip isn’t useful. I’m sure it was to some users. But Hotjar’s emails did absolutely nothing for user/product fit.

I had no control over how I progressed through features.

No choice over what to learn and how/when to progress to my next step with the product.

I would have appreciated a few choices instead of big red buttons in every email. To either skim all of Hotjar’s features or do a deep dive into one of them. Or to check out a webinar on a particular feature instead of trying the app out myself.

I realize that total user control is a designer’s nightmare. Configuring layout, content, and functionality can be complicated for the designer and too many choices can overwhelm a user.

I’m not suggesting you customize your entire product. Just the initial phase of learning. When users are learning, giving them a choice between a webinar and exploring the app is a great way to let them decide what kind of next step they would like to take.

2.4 Principle #3: Build on the experiences users have had with your market

Researchers agree that experience is a critical component of learning in adulthood. What they debate is exactly how adults learn from experience. Sharon Merriam, Rosemary Cafferella, and Lisa Baumgartner explore them all in their book Learning in Adulthood.

What’s more relevant to us is what all the theories of ‘the how’ have in common. “Central to all of [the views]” they write, “is the notion that learning from experience involves adults’ connecting what they have learned from current experiences to those in the past as well to possible future situations.”

When it comes to the awareness of the problem scale, a user can fall anywhere from ‘I don’t know enough to check out features as yet’ to ‘I’ve evaluated competitors, show me what you’ve got’.

A good way to work an educative element into emails catering to users with a high awareness of the problem is to take advantage of their experiences.

By positioning the way you’re thinking about things against the norm you can get users to see the problem like you do even faster.


Project management is a huge market. Anyone who’s had to work with other people has had to rely on project management tools to do it. Of course, this means project management software has been around much longer than, say, in-app messengers.  

When I arrived at, I’d already used a bunch of project management tools. So I was broadly aware of the norms in project management .’s welcome email nailed positioning themselves against  them. They promised a more visual, intuitive approach to project management.

The problem was the ‘do this next’ buttons that arrived with every email in the rest of their drip campaign.

The thing is I liked’s promise and I was excited to test the product out. But it was still a product that I had to learn. If they’d gone into the thought work behind their approach, I think my learning could have been faster.

For example, in a follow-up email, offered templates that I could have put to use. Every project management tool offers templates. Instead, if they had offered templates after they told me how their templates work better because of their more visual approach, I would have gotten to the crux of them (and used them) faster.

If there’s one thought I can leave you with…   

“The end is the cause,” Aristotle said.  

When you understand that a rabbit’s end is to preserve itself, you have an answer to why it runs from the fox. When you understand that a rock seeks to move towards the center of the Earth, you gain some insight into why it deforms the foot that got in its way.

Too often, I encounter user onboarding emails that exist because the product wants me back. I’m accosted with fancy features, popular webinars, and next steps that don’t speak to my end. I’d love to encounter more that exist because a product is invested in the better life I’m after.

Let a user see that your ends are hers.

Get her to the second use of your product because she can find her better life there.