The Definitive Guide to User Onboarding: Part Three

Editor’s Note: This article is Part 3 of a 3-part series that was first published on the Product-Led Institute blog here. You can read Part 1 here and Part 2 here.

Based on the user onboarding emails covered in Part 2, I’m going to share how you can create a just-in-time onboarding email sequence that converts.

Create a Just-In-Time User Onboarding Sequence

Signals tell us when we should send a specific email or enroll a user into a new campaign.

In my Just-In-Time Email Onboarding Sequence above there are only four signals:

  1. Signup
  2. Quick Win
  3. Product-Qualified Lead (PQL)
  4. Customer

Each of these signals tells us an important part about where the user is in their journey.

Based on the signal, we can enroll people into different email onboarding tracks. For instance, if someone experiences a quick win in the product, we can now send emails based on how to dive deeper into the product.

Or if someone becomes a Product Qualified Lead (PQL), we can now send sales touch and case study emails to encourage users to upgrade.

You’re soon going to see how we can use all of those emails we just talked about.

Before diving in, I wanted to point out one small detail that is easy to miss. In the onboarding tracks, if you see a lightning bolt underneath the email, it is a trigger-based email. Whereas if you see a clock underneath an email, it is time-based.

Now, that we’re on the same page, let’s dive in!

Just-In-Time User Onboarding Track One – Quick Win

Signal: Signup

Key Outcome: Quick Win

As you can see above, when someone signs up it signals the start of the email onboarding track. As soon as someone signs up, it should trigger a welcome email immediately after.

What you might find unusual is that the next three steps all focus on usage tips.

As we covered earlier, usage tip emails only try to accomplish three things:

  1. Directing users to a specific in-app page (e.g. “Manage users” page)
  2. Linking to specific help center articles or blog posts (e.g. “how to invite a user from outside your company”)
  3. Giving actionable best practices, or inviting abandoned users back

In the first onboarding track, the only thing we care about is getting someone to experience a quick win in the product.

For instance, if we operate a business intelligence software solution, our first quick win might be setting up a dashboard to visualize our analytics. At first, every email we send to new users should be focused on hitting that income.

One thing that is easy to miss when it comes to Email Onboarding Track One is that you might not need to send any usage tips to users if they accomplish the quick win in the first-run onboarding experience (aka the first time someone uses a product).

Let’s say you’re CrazyEgg, a heatmap tool, and your first quick win is getting users to upload a tracking script to their website. If they accomplish this in the first-run onboarding experience, why would you bother sending any more emails about how to upload the script? On the flip side, if you didn’t upload the script, it would be extremely helpful to have emails that guided users how to upload the script. Wouldn’t you agree?

Once your users have accomplished a quick win, it’s time to think about how you can turn your new users into repeat users.

According to Intercom, 40-60% of users who sign up for a free trial of your software or SaaS application will use it once and never come back.

That’s a lot of waste. One of the best ways to bring people back is through Email Onboarding Track Two.

Key Takeaways:

  • User Onboarding Track One focuses entirely on helping users experience a quick win in the product
  • The only two emails you need to include in onboarding track one are welcome and usage tip emails
  • User Onboarding Track One is not focused on selling at all

Just-In-Time User Onboarding Track Two – Product Qualified Lead (PQL)

Signal: Quick Win

Key Outcome: Product Qualified Lead (PQL)

Email Onboarding Track Two starts as soon as someone experiences a quick win in the product and ends when someone becomes a PQL.

If you’re not sure what a PQL is, I recommend reading the Beginner’s Guide to PQLs.

PQLs help us identify users who have experienced the product’s core value and are most likely to convert as customers.

For a business intelligence solution, a PQL could be a user who creates their first few dashboards and shares it on a TV display.

For Drift, a PQL could be when someone has had 100 chats on their website using the tool.

For CrazyEgg, a PQL could be as simple as viewing your heatmaps and user recordings multiple times and uncovering an insight.

A PQL is unique to every business, however, the one commonality is that a PQL is used to monitor when users experience meaningful value in the product.

One of the best models to get more users to become a PQL is inspired by Nir Eyal’s book, Hooked.

What I love about Nir’s model is that there are only four actions you need people to take in order to create a habit-forming product.

As you can see, you start with a trigger, get people to take an action, which (ideally) results in a reward and an additional investment in the product. This cycle, if repeated, builds long-time users.

Leave one item out, like rewards, and you risk losing users.

To get a better idea of how to use this framework when it comes to user onboarding, I’m going to break down each item into more detail.


There are both external and internal triggers.

External Triggers

External triggers are much easier to control than internal triggers.

Here are a few examples of external triggers that you can use to increase the odds of having a user come back to your product:

  1. Paid Triggers – Advertising
  2. Earned Triggers – Public and Media Relations
  3. Owned Triggers – Website, Email, & Blog

External triggers are comparable to lighting a match. They’re typically very bright and powerful at the beginning but then they lose their effectiveness fast before ultimately not working.

That’s why welcome emails typically have a 60%+ open rate and then the open rates dramatically drop off.

The best way to use external triggers, like user onboarding emails, is to encourage users to experience meaningful value in your product.

Our whole goal in this track is to use triggers to spark an action that requires an additional investment of time in the product, which inevitably results in a reward.

The more times we take users through our habit-loop, the more likely they are to stay as users and eventually customers.

Internal Triggers

Internal triggers, on the other hand, only become stronger and stronger.

Internal triggers manifest in the mind.

Here are just a few examples of internal triggers that I’m sure you’re familiar with:

  1. When you’re bored or sitting alone at a restaurant, do you pull out our phone and check Facebook?
  2. When you need a quick reply from a coworker, do you send an email or a message on Slack?
  3. When you want to write a blog post, do you open up Google Docs?

Each time you use an internal trigger and it results in a reward, our brain is wired to remember it. Depending on how big the reward and dopamine rush, products can become highly addictive in a short period of time.

The process of creating strong internal triggers is comparable to trying to find a new pizza shop that your friends have been raving about.

The first time you have a pizza craving and decide ongoing, you might make a few wrong turns, take some side roads, eventually pull out Google Maps, and end up taking an inefficient way of getting there.

But, if the pizza is amazing, you’re coming back. However, the next time you shave off 5-minutes from your previous route.

By the third time, you’re taking the highway and shave off 15-minutes from the first route you took.

Although we’re not selling pizza, our brains are constantly looking for more efficient ways to help us get to our yummy dopamine rush.

Internal triggers start as inefficient paths in the brain and consistently become more efficient the more we use them.

Internal triggers do take time to build, but are a prerequisite to building a truly habit-forming product.


The actions you ask your new users to take will have an incredible impact on if your users end up upgrading or not. In your user onboarding emails, if you ask people to do anything that doesn’t help people experience a meaningful reward in your product, you can hurt your free user to paid conversion rate.

Good actions to ask your users to take often have these characteristics in common:

  • The action is closely tied to experiencing a reward
  • The reward leads to an additional investment in using the product

Whereas, bad actions you want to avoid are:

  • Not aligned with experiencing meaningful value in the product;
  • Not specific to what users have done in the product;

With that in mind, what are the three actions you want people to take in your product? What actions currently result in a reward and an additional investment in your product?

To help you answer these questions, here are a few examples from well-known products:

For Soapbox by Wistia, whenever you record your first video and don’t share it with coworkers, they send you a user onboarding email encouraging you to take the action to share it with your colleagues or prospects.

Once you take the action to share the video, Wistia is teeing you up to experience a reward. Whether that be saving you time explaining something complex or having your co-worker say they really enjoyed the video.

This cycle naturally leads users to want to invest more time and energy into using the product.


This is where the user does a little work. The user “pays” with something of value: time, money, social capital, effort, emotional commitment or personal data.

“Investment is about future rewards that make the next action more likely.” – Nir Eyal, Hooked

Without any form of initial investment, most software products aren’t that valuable.

If you think about Salesforce, the CRM solution gets its value from integrating with other tools, managing your contacts, analyzing your deals, and building reports to understand your business better.

By definition, it’s a Do It Yourself (DIY) kind of deal when you sign up. Sure, the Salesforce team can onboard your team but you need to show up, invest your time, learn how to use the tool, and then train your team how to use it.

It isn’t until you invest the time, energy, frustration, and money until you start to see how it can truly help your business.

The tricky part about investment is it is unrealistic to expect your new user to complete all the required onboarding tasks right at the beginning.

Much like you wouldn’t expect to get a six pack the first time visiting the gym. It takes time, but what you need to do early on in the onboarding process is understand the first few investments you need your user to take.

In many cases, this could be breaking down the steps it takes for a user to experience a quick win in the product and then using those steps as the first investment you ask users to take.

That way users won’t get demotivated right at the beginning. If the user can see progress, you’ll be able to keep them motivated.

For Buffer, the first investment they ask users to take is to connect their social media accounts. This small investment brings the user much closer to experiencing meaningful value in the product. 

For Wave, they start by asking you what you’re planning on using the product for. This product tour helps eliminate a significant investment of time for users who don’t want to set up all the features in the account at the beginning.

To recap, if you want to build a habit-forming product, you need to create habit loops that start with a trigger and end with an additional investment in the product. If you can do this, you’ll have a habit-forming product that hooks users to continue using your product.

Once your users are hooked, the most logical next step is asking users to upgrade.

  • User Onboarding Track Two is all about building a habit-forming product
  • The goal is to use habit loops which include triggers, actions, rewards, and investments that motivate the user to continue to use the product
  • Although we can rely on external triggers (like email) to motivate users to come back to the product, external triggers quickly lose their effectiveness over time. To build a habit-forming product, you need to invest in building internal triggers

Just-In-Time User Onboarding Track 3 – Convert

Freemium and free-trial signups have one thing in common: Neither generates revenue. – Derek Gleason, ConversionXL

For the first two onboarding tracks, the entire focus has been devoid of generating revenue. In case you were curious, that wasn’t by accident.

You see, where most people mess up in user onboarding is trying to monetize too quickly. One of the biggest mistakes I see happen over and over again is skipping the first two onboarding tracks and focusing on converting users.

It’s so easy to do. By not focusing on the first two onboarding tracks, you will inevitably have a terrible free to paid conversion rate, unless your product is one-of-a-kind. So, naturally, you jump to how to improve free to paid conversion rates.

If that’s you, go back and read the first two onboarding tracks. Without that foundation, all of the strategies and tactics I’m about to share won’t be anywhere near as effective.

If you’re still reading this, I’m going to assume that you’ve read the first two user onboarding tracks.

At first glance, Onboarding Track Three looks a bit overwhelming.

You have a bunch of different emails, but one thing is clear. Every email is focused on upgrading the user to a paying customer.

As far as emails go, you have:

  • Sales Outreach Emails
  • Case Study Emails
  • Better Life Emails
  • Trial Expiry Emails
  • Trial Extension Emails
  • Post-Trial Surveys
  • New Customer Welcome Emails

Now, that’s quite a lot of emails. By this point, you might be thinking something like, “Wes, if I realistically sent out every email in Onboarding Track 1,2, and 3, that would overwhelm my users.”

My response to you would be, well, not necessarily. Each of these onboarding tracks is trigger-based. So if your user experiences a quick win in the product the first time testing out the product, you wouldn’t need to send them any usage tip emails and would auto-enroll them into Onboarding Track Two.

For Onboarding Track Three, if the user upgraded when they received the case study email, you’d immediately stop sending them more emails to upgrade. Or at least I hope you would.

The beauty of these three onboarding tracks is that they are specific to where the user is in their journey.

Whenever it comes to Onboarding Track 3, it’s important to note that how you reach out to each user is entirely dependent on the average LTV of each customer.

If you have a high LTV, you can afford a higher CAC and a more manual sales approach. Or if you’re like many SaaS businesses that fit somewhere in the middle, you’ll want to deploy a low-touch sales model as soon as someone becomes a PQL.

How you reach out really depends on what your average LTV is. Although this is not a rule, if you want to grow sustainably, you’ll inevitably have to match your sales approach with your average LTV so that your CAC doesn’t destroy your margins.

If you do go with the low-touch approach, I would recommend learning more about how Atlassian has grown it’s low touch sales model into an automated sales machine.

Key Takeaways:

  • The entire focus for Onboarding Track Three is to upgrade users into customers.
  • How you reach out to users is dependent on what your average LTV is. If you don’t match your outreach approach with your
  • LTV of a customer, you’ll risk running an unprofitable business.
  • Once a user upgrades, you need to remove them immediately from Onboarding Track Three.

Just-In-Time User Onboarding Sequence Review

When it comes to user onboarding emails, you need to catch people where they are in their user journey. Each email we send out needs to help the user progress further and help them accomplish what your product enables people to do.

To recap, Onboarding Track One focuses entirely on helping users experience a quick win in the product.

Every email in this track is trigger-based. You will always need to send out the welcome email, however, when it comes to usage tip emails, you can skip them if users already accomplish those recommended actions in the product.

For Onboarding Track Two, it starts the second a user experiences a quick win in the product.

The first email in the track is a usage review, however, that can be modified depending on if you can showcase value from the product.

For CrazyEgg, this could be showcasing a user’s heatmap of their homepage in an email.

For some products, however, it’s not that simple to showcase your product’s value as soon as they experience a quick win in the product. If that’s the case, you can always skip the usage review email or delay it.

For the trigger emails, all you’re trying to accomplish is helping the user take a meaningful action in the product that results in a reward and additional investment in the product. By doing this, you’re able to build hooks into your product that are essential to building a habit-forming product.

For Onboarding Track Three, the entire focus is to upgrade users.

Typically sales will reach out as soon as a user has become a PQL. That way sales is only focusing on the leads that are most likely to close.

For the Case Study emails, you can have your customers help you handle any objections your users may have whether that be through a video testimonial or case study.

For your Better Life emails, you want to focus on highlighting the main benefits of your product and prompt users to upgrade.

For your Trial Expiry emails, you want to focus on communicating the value of your product while reminding people that their free trial is about to expire.

For your Post-Trial Survey emails, the whole goal is to learn why people don’t upgrade and then enroll each user into a follow-up sequence.

If we put all the email onboarding tracks together, you’ll have a Just-In-Time onboarding system that converts free users into paying customers.


Wes Bush helps B2B SaaS leaders acquire and convert more users at Traffic Is Currency. If you want to learn who your best customers are and, more importantly, what frustrates them to action, you can steal his free course at
You might also like ...
10 Critical Brand Marketing KPIs You Should Be Measuring in 2020
When it comes to creating new marketing campaigns for your brand, data is king. Using a data-driven strategy ensures that...
by Kevin Payne
Customer Success
Why Customer Success Leaders Aren't Getting a Seat at the Table

With only lagging metrics in their toolset, customer success leaders can’t really drive strategy at the executive level. Here’s Chris Hicken, former president at UserTesting, on how to change that.

by Chris Hicken, CEO at 'nuffsaid
Customer Success
Practical SaaS Retention Strategies That Move the Needle (Part Two)

Learn several strategies to improve retention in this two-part series.

by Corey Haines