User Onboarding Email Best Practices

User onboarding emails can help you take your trial engagement from “okay” to “incredible.”

Today, we’re going to look at how to build a trial engagement journey that gets people to keep coming back again and again and again. From there, we’re going to help you turn your users into happy, paying customers. All through the power of onboarding email sequences.

There are three core elements to this discussion:

  1. User onboarding email best practices
  2. Learning how to create a behavior-based content engagement program
  3. Designing a trial engagement journey

We’re going to go through 3 onboarding tracks, from first visit to conversion, with examples of what to do and how to build them out.

Five Must-Have User Onboarding Emails

There are five main onboarding emails we’re going to be referencing and using throughout this article:

  • Welcome Email
  • Usage Tips
  • Sales Touches
  • Usage Reviews
  • Expiry Warning

Let’s take a closer look at some of them before we go any further. This’ll help a lot when we get into the details later on.

Welcome emails

  • Should aim for 60%+ open rate
  • Have two purposes
    o To train your audience to open your emails
    o To set the expectation of what is coming next
  • Have no images and are focused purely on clarity. Having no images greatly reduces your risk of ending up in the spam folder or confusing new users. This is the most important email, so play it as safe as possible to be as smart as possible
  • Are plain text
  • Have a CTA

Check some examples of good welcome emails below:

1st Example Of  User Onboarding Email

This welcome email is focused on determining the Job To Be Done for each user.

2nd Example Of Onboarding Email

This welcome email is introductory, human, and aims to build connection and motivation.

Welcome User Onboarding Email

This final example is all about moving new customers towards value actions and ‘Aha’ moments.

Each one has its value and will suit different companies with different products.

Usage Tips

  • Direct users to a specific in-app page (e.g. Manage users page)
  • Link to specific help center articles or blog posts (e.g. how to invite a user from outside your company)
  • Give actionable best practices, or invite abandoned users back – a key part of onboarding email sequences
Example Of Usage Tips

With Soapbox, creating a video is not enough – sharing your first video is their ‘aha’ moment. This Usage Tip is helping the user move to the next step and achieve that all-important value.

Sales touches

  • Could be sent out as a “success meeting” to celebrate the user achieving an ‘aha’ moment and to get more use out of the product
  • Inviting inactive users to an orientation demo (e.g. “30 minute crash course on how to share documents and collaborate between teams”)
Example Of Sales Touches

See how this example is so tightly user-focused? The goal is to help me achieve better value out of their product, not to make me spend my money.

Usage reviews

  • Sent halfway through a trial and the onboarding email sequence to give users a bird’s-eye view of their progress and suggest areas to explore further

Showcase your value metrics in these emails! By sharing these early, your users are going to ‘get’ how your product works for them and understand its core value quicker.

Example Of Usage Reviews

The key metric for ZenDesk is time taken to respond. So by sharing this monthly snapshot, they help to frame usage that will aid users in achieving value.

2nd Example Of Usage Reviews

This is as simple as you can get, but it’s Twitter’s goal! Engagement begets engagement.

Expiry warnings

  • Sent with one week left in the trial to remind users to buy. Be helpful and confident, not pushy and salesy.
Example Of Expiry Warning

These are a little less exciting, but they are incredibly important as they represent one of the last few chances in your onboarding email sequence to convert trial users into customers. This is a really good example from Basecamp that does a great job of restating the value to the user.

User Onboarding Email Best Practices

Before we get into best practice and big ideas for onboarding email sequences, it’s important to point out something you really want to avoid.

Do not send nagging emails!

If you aren’t sure what a nagging email looks like, this is a good example from my own inbox. On the surface, it seems okay, but once you dig into it with your Product-Led hat on, you’ll see some major issues.

Example Of A Nagging Email

Nagging emails:

  • Assume the recipient already knows that the product is worth their time
  • Assume that since someone signed up for a trial, they’re immediately ready to buy
  • Repeat the same request, over and over
  • Don’t focus on how the reader benefits, only the sender
  • Are cold, impersonal, and solely concerned with making a sale

A big problem with the example email above is that the title shows they don’t know whether I have or haven’t downloaded their app. This gives away that it’s a time-based email, not one that’s personalized to my place in the customer journey and with no consideration of how I am using their product.

Time-based content can be useful in your onboarding email sequence, but you have to know how to use it correctly.

If you want to prevent nagging emails, make sure you focus on:

  • Addressing common questions and objections at a given stage in the funnel (based on behavior)
  • Educating users about how you can solve their pain
  • Explaining benefits (not features) of your product
  • Giving users a single, clear call to action

How to create a behavior-based user onboarding email program

Traditional onboarding emails are:

  • Not outcome-driven
  • Not tied to what the user has done in the product
  • 100% time-based
  • Feature-driven
  • One-size fits all

It’s not a comparison you might expect, but we can learn a lot from the manufacturing industry when it comes to creating behavior-based onboarding email sequences.

For example, Toyota operates an exemplary just-in-time system. When someone buys a car, they go out to design and buy the specific parts for each order rather than having a huge inventory sitting around. The whole system starts the ‘user signal’ of someone placing an order.

We want our onboarding emails to be just-in-time, not just-in-case.

Design a trial engagement journey

We don’t want to eliminate time-based emails from our onboarding sequence, as they serve an important purpose, but we’re trying to find the right places for them and to merge them with behavior-based emails.

We’re going to dive into three different tracks you can setup to incorporate time- and behavior-based emails:

  • Track one (quick win) - is the essential onboarding email sequence, triggered when a user starts a trial
  • Track two (getting them hooked) – is triggered after a quick win/’aha’ moment has been achieved
  • Track three (convert) – is intended to convert a trial user from free to paid

Each one of these tracks is essential in your customer lifecycle and each one leads into the next. They all start with user signals and have been proven time and time again to drive success and conversions.

Important note: With all of these tracks, you do not need to take a user through every step. If they achieve the end goal after one or two emails in the sequence, they do not need to be sent the others!

Track One - Quick Win

This track is all about getting users to the first quick win in your product. Your onboarding emails in this track should break down the steps they need to take to get to that quick win.

Onboarding Email Track 1

The signup is the signal for your Welcome Email to be sent.

Don’t be afraid to send follow-up emails. ~60% of people aren’t going to open them at the first attempt, so follow them up with a message that asks: “Did you get to that last thing I sent? Here’s why I thought it would help and how it will benefit you.”

These Usage Tips go all the way through to the user achieving their first quick win.

Note how there are no sales emails in this track! This is really intentional. This first track is just about getting users to become successful.

The goal with these onboarding emails is customer success, not product sales.

Track Two – The Hook

This track is all about getting users to experience the ‘aha’ moment again and again (and using external triggers to drive them to adopt a new behavior).

Nir Eyal’s ‘Hooked’ lays out a great formula for forming habits:

Formula For Forming Habits

External triggers can include:

  • paid triggers (advertising)
  • earned triggers (public and media relations)
  • relationship triggers (word of mouth)
  • owned triggers (email and other assets you build)

But you can’t just rely on external triggers, as they have very short half-life. After a while, they lose their effectiveness. An ad is most effective on its first impression, not its tenth.

So, we are always searching to set up internal triggers and include them in our user onboarding emails.

Internal triggers manifest automatically in your mind and turn your product into the first thing that comes to mind when a user has the Job To Be Done that your product solves.

For example, let’s think about Twitter.

You get a notification on your phone (trigger), you open Twitter (action), you see someone liked your tweet (reward), and then you spend time on the platform or repeat the action by tweeting more (investment).

So, Track 2 emails are built on these habit-forming principles. It could look something like this:

Onboarding Email Track 2

Everybody’s Product Qualified Leads (PQLs) are different, but the steps in this template will always be transferable if you reverse engineer them from your PQL criteria.

If you know where you want someone to be, go backwards through the steps they need to take to get there.

Success measure: Signup-to-PQL rate = Signups/PQLs

Track Three - Conversion

Track Three sees you aligning your users’ perceived and experienced values with your product. This is when users understand your product’s value proposition on their own terms.

When they make it to this point, your product has sold itself!

Onboarding Email Track 3

The moment a user becomes a PQL is the best time to begin sales outreach. Do not hesitate or hold back from contacting your PQLs because you will never have a better chance at converting them. You can set this onboarding email to trigger within minutes of them becoming a PQL.

If they don’t convert immediately, then you move them along the track, sharing case studies that show how other users are benefiting from your product. The ‘Better Life’ steps will help you outline the experienced value your users achieve and the CTA is simply to upgrade.

If your users do not convert at this stage – all hope is not lost!

Offering trial extensions and post-trial surveys are a great way to give you and your trial users a deeper understanding of your product and the way it is used. These are two vital tactics to use if you want to improve your conversion rate and fit seamlessly in as part of these onboarding emails.

Success measure: PQL-to-Customer rate = PQL/customers

Build your moat

What is your competitive advantage as a business?

In the (distant) past, people would build moats to make it hard for others to take down their castle.

Our businesses also need moats and the best moat you can have is successful users. There is nothing that can breach our defences if we have successful users.

Our customers are all different and we can’t hand-hold every one of them, so there are inevitably different categories of contact and complexity that they fall into:

  • High-touch (reserved for enterprise and complex/expensive products)
  • Low-touch (most common, built on email and onboarding flows. Scalable, automated, and personalized)
  • No-touch (completely streamlined onboarding flow, often has a low lifetime value (LTV))

Our customers fall into these different categories of sales complexity based on their Customer Acquisition Cost (CAC).

The LTV of our product for each potential customer can help us determine the best way we can help our customers.

For instance, a high LTV product or customer means we can afford to invest in sales agents or customer success agents.

For most SaaS businesses, high LTV customers do not make up the bulk of their sales.

That’s why, today, we’ve focused on low-touch approaches and how to use onboarding emails as an extension of our product.

Pop quiz, homework, and bonus reading!

To do a little revision, see if you can remember:

  1. What you need to measure in order to improve your PQL conversion rate
  2. How to avoid sending nagging emails
  3. Which lifecycle emails focus on showcasing your value metrics

Take what you’ve learned and build out a visual flow of what Track One will look like for your business. Take time to identify the actions that will trigger each email in the sequence.

And now that you’re really into the flow of things, take a look at these other resources to help you get a deeper understanding of onboarding emails that will convert your trial users:

Wes Bush
Wes Bush
Wes Bush is the bestselling author of Product-Led Growth. He’s a renowned Product-Led Growth pioneer and has challenged an entire industry to find a better way to approach SaaS growth.