Email Onboarding Tricks Used By Drift & Dropbox To Boost Conversions

Having trouble onboarding new users to your SaaS product? Start by looking at your emails. Here's how Drift, Dropbox, Camtasia and Smartsheet do it.

SaaS Onboarding Strategy

You can lead someone to your SaaS app, but you can’t make them use it. In fact, you’re starting to think these people are, well, kind of slow. After all, they signed up for a free trial six days ago, and they’ve only logged in once.

You’ve only sent them 17 onboarding emails…

Bribed them with a free t-shirt…

None of it makes sense. You have dozens of case studies. Thousands of happy customers, including ones on the Fortune 500. So what’s the deal with this person who can’t even invite their team members to your app?

This pattern might go on for a few days before you’re ready to throw in the towel with one last desperate plea to sell them a plan. But your data knows better: they’re gone for good.

The Surprising Factor That’s Sabotaging Your Onboarding Stats

Despite blog posts touting onboarding emails as a must-have, you’re not just buying it. Reminding users to log in? They need instructions to install something? Surely, they can figure things out.

But you’re forgetting…

The app is your baby. You use it every day. Know every feature by heart. For heaven’s sake, you probably have parts of the codebase memorized.

Meanwhile, your free trial users have only seen it once and most of them probably signed up while scarfing down a bag of Cheetos and licking their fingers.

In other words, your onboarding emails might not be working because you have an expert blind spot. It’s defined as:

“The inability to perceive the difficulties that novices will experience as they approach a new domain of knowledge… advanced content knowledge without concomitant advancements in the knowledge for how novices actually learn within a content area can lead towards views of instruction that align more closely with the organization favored by the [experts] than the learning needs of [users].”

Translation: It’s why most of us snort with laughter when we see the “How to Draw an Owl” meme.

How To Draw An Owl

For a trained sketch artist it’s probably a cinch to draw an owl, starting with two overlapping circles. But for the rest of the population who still draws like a 6-year-old? It’s enough to make us crumple the piece of paper and never attempt to draw again.

How To Get Over Your Expert Blindspot

You might have expert blind spot. But the truth is, your user is a problem too. They might be lazy. Or busy. But either way, you can’t force them to do anything.

But there is a way to encourage certain behaviors. According to B.J. Fogg, the ability to persuade someone towards action has to do with the intersection of three factors: Motivation, Triggers, and Ability.

Motivation, Triggers & Ability

For your free trial user, they’ve already signed up. There’s a little part of them that wants your product to work for them, which makes up the Motivation.

The Trigger is the call-to-action in the email, whether it be to log in, try out a feature, or finish setup.

Which leaves us with Ability, which is where onboarding plays a role.

So if you need some help breaking through your expert blind spot, put yourself in your user’s shoes and ask yourself these questions, using Fogg’s Simplicity Factors to guide you:

  • How much time does it take to set up and use the app?
  • Can I afford the app – and make it worthwhile?
  • Is it difficult to use this app?
  • Does the app require me to think in new or different ways I’m not used to?
  • Do I have to break rules or convention to use this app?
  • Does this app fit into my daily routine?

Use this exercise to break through your expert blind spot, and find the onboarding gaps in your SaaS app.

3 Ways To Motivate Free Trial Users In Your Onboarding Emails

By now, you may have realized that your app is more confusing to use than you ever could have imagined.

While you can spend the time convincing your engineering and design teams to prioritize onboarding in their next few sprints, you would prefer to fix this problem sooner rather than later.

You do that by rewriting a few of your onboarding emails. There’s no exact definition of what constitutes an onboarding email, but they typically include email copy like:

  • How to install the app
  • What features the app has
  • What integrations the app has

Though talking about it can be dull. To make sure these emails change a user’s existing behavior, use these three principles:

  1. Show the user’s progress when they’re installing the app
  2. Tie features to an outcome the user feels is achievable within their current means
  3. Connect an integration to a user’s everyday work habits

Let’s break each one down.

Show Them Their Progress When “Installing” Your App

Not every SaaS app is a one-click setup. In fact, the more steps there are, the more a user is likely to get distracted and discouraged.

While it might be tempting to refactor your code to create an easier installation process, we can use onboarding emails to bridge the gap. We just need to show the user how far they’ve come…and how much effort it will take to finish the step.

This is known as the endowed progress effect, which is defined as:

“People [who are] provided with artificial advancement toward a goal exhibit greater persistence toward reaching [that] goal.”

Translation: If people believe it won’t take long to accomplish something, they will be motivated to finish it.

In a study done at USC, researchers handed out loyalty punch cards at a car wash. Half of the group was issued empty punch cards, whereas Group B was given punch cards with two pre-issued stamps. Regardless of which group they were in, each member had to purchase eight car washes to be eligible for a free one.

They found out the rate of completion of the punch card for Group B was double the rate of completion of Group A. Even though both groups still had to pay for eight car washes!

You can show a user their installation progress in your onboarding emails in a visual format, the way Dropbox has done here:

Dropbox Onboarding Email

However, there is a way to nail endowed progress using just words. See this onboarding email example from Drift:

Drift Onboarding Email

Whether Cara knew it or not, using the phrase “SO close” is a case of endowed progress. She got the reader to feel a little bit of anxiety because they never finished setting up their account.

And she even offered to help the user finish installation of their app – an example of stellar customer success.

When writing onboarding emails, consider how you can use endowed progress to get users to finish installing your app – even if it’s as simple as telling the user how “close” they are to finishing something.

Tie Features To An Outcome They Feel Is Achievable

When I write onboarding email campaigns for clients, I’m often given a list of features to highlight in the emails.

Don’t get me wrong – this is a great start. But this is when I start working some copywriting magic with a formula called FAB.

FAB stands for:

  • F = Features. What can your product or service do? What does it offer?
  • A = Advantages. Why is it helpful? What problem(s) does it solve?
  • B = Benefits. Why is this relevant to the reader? What does it mean for them?

Using this framework helps you think beyond saying what the feature does on a tactical level…and move towards explaining how life will change for the user if they use this product or service.

But sometimes users are irrational, and despite wanting their life to get better, they resist. After all, I can think of many instances where I resist paying $25/month for a tool because I am attached to my clunky (albeit free) method.

According to neuro-linguistic programming experts Hoobyar, Dotz, and Sanders, this is incongruence, or when “[one] feels conflicted about a goal or a situation.”

So even a user KNOWS they can save time or improves their life with your app, they are afraid of change. In their irrational mind, it might take more time and effort in learning to use your tool, than do it the way they’ve done it in the past.

Therefore, when pushing features in your onboarding emails, be cognizant of your user’s goals and allude to the change they can make as result of your product – but don’t be too far-fetched about it.

Let’s use this email from Camtasia, a video editing tool, as an example. In this particular email, they’ve highlighted their audio editing features.

Camtasia Onboarding Email

Since Camtasia targets users with no prior video experience, it’d be odd if Camtasia started talking about the ability to add reverb and compression – after all, their target user has no idea what those things even are.

But Camtasia describes feature as editing mistakes and adding music tracks. And they allude to the goal that they want you to accomplish as a result of learning to master these features: Sounding like a pro.

If I were rewriting this email, I might spend a little more time expanding on what “sounding like a pro” means – especially for someone whose video editing for the first time.

So when discussing features in onboarding emails, consider the user’s internal conflict about accomplishing their goals. By talking about realistic goals they can achieve as a result of using your product, you can overcome it…and get closer to converting the user into a paid customer.

Connect An Integration To Their Everyday Work Habits

The last thing a user wants is “another tool.”

When you send users an email encouraging them to integrate your app with Slack, Github, or any other tool they use on a regular basis, it’s not always obvious how it will improve the way they currently do their work.

Which is why if you’re writing onboarding emails, you need to understand exactly how your product fits into your user’s everyday work habits.

And when you figure out exactly how that happens, you can take advantage of a user’s ability to stack habits together.

While many notable psychology scholars have discussed the phenomenon, I like James Clear’s definition:

Stacking a new habit on top of an existing habit. Because the current habit is strongly wired into your brain already, you can add a new habit into this fast and efficient network of neurons more quickly than if you tried to build a new path from scratch.

Meaning you’re not just encouraging a user to connect two apps. You’re building a new habit in your user’s brain to associate with their existing ones. Which leads to a quicker product adoption.

Let’s look an email example. For SmartSheet users who work in Sales, this Salesforce integration is a nice-to-have option.

Smartsheet Onboarding Email

But how does it tie into the way sales people currently use Salesforce? Or how they use Smartsheet?

If I were to rewrite this email for free trial users of SmartSheet, I would talk more about the pain of switching between Salesforce and another spreadsheet service on a user’s computer screen.

I’d also highlight the annoyance of keeping multiple types of information in two different SaaS apps…and how the integration makes it easy to sync information, regardless of which app gets updated.

By calling out the reasons why it’s in the user’s interest to connect two apps, you eliminate their hesitance to add yet “another tool” to their workflow.

Finally, A Solution For The Oblivious Free Trial Users

Any SaaS founder who’s having trouble converting trial users into paid accounts would be irrational NOT to look into improving their onboarding emails.

You’ll need to overcome your expert blind spot to properly evaluate your user’s abilities, using these six questions to guide you:

  • How much time does it take to set up and use the app?
  • Can I afford the app – and make it worthwhile?
  • Is it difficult to use this app?
  • Does the app require me to think in new or different ways I’m not used to?
  • Does I have to break rules or convention to use this app?
  • Does this app fit into my daily routine?

And when you get around to writing your onboarding emails, remember to:

  1. Show the user’s progress when they’re installing the app
  2. Tie features to an outcome the user feels is achievable within their current means
  3. Connect an integration to a user’s everyday work habits

Add these things to your onboarding emails, and you’ll have more trial-to-paid conversions than you’ll know what to do with.

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Sophia Le helps SaaS companies convert trial users into paying customers, combining email with the psychology of persuasion. Visit her website for a free fill-in-the-blank welcome email template and follow her on Twitter.