The Definitive Guide to User Onboarding: Part Two

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

User Onboarding Starts Like Building a Car

When assembling a car, you can have all the parts you need but if you don’t know what tools to use, there’s a slim chance you’re going to build a car that can get you from point A to point B.

User onboarding is no different.

You can have all the right parts but if it’s not assembled together properly, you’ll be left with an expensive “solution” that doesn’t work. And that’s no fun.

The problem I find most people have is that they just don’t know what user onboarding tools they can use to improve their free user to paid conversion rate.

Who can blame them though? There are countless user onboarding tools and it’s only becoming a more crowded space as more brands adopt product-led growth.

To simplify all the tools we can use to assemble our high-converting user onboarding flow, let’s divide all the tools into in-app and conversational onboarding tools.

In-App Onboarding Tools help users adopt the product in the application itself.

Conversational Onboarding Tools work to educate users, bring them back into the application, and eventually upgrade their account.

When it comes to in-app onboarding tools, here are the most common tools you can use:

  • Welcome Messages
  • Product Tours
  • Progress Bars
  • Checklists
  • Onboarding Tooltips
  • Empty States

For conversational onboarding tools, here are the most common ones you can use:

  • Lifecycle Emails
  • Push Notifications
  • Explainer Videos
  • Direct Mail

Even if you’re familiar with the majority of these onboarding parts, I’m going to walk through each one so that you can be confident that you’re using the onboarding tool in a way that will improve your free user to paid conversion rate.

In-App User Onboarding Tools

In-App User Onboarding Tools help users adopt the product in the application itself.

Ideally, every tool below works in unison to help users experience meaningful value in the product.

Here are the main in-app user onboarding tools I’ll break down:

  • Welcome Messages
  • Product Tours
  • Progress Bars
  • Checklists
  • Onboarding Tooltips
  • Empty States

Welcome Messages

If you knock on a door to a friend’s house, what kind of response would you expect?

Would your friend welcome you? Or would they not say a single word and let you walk around their house and eat the food in the fridge?

In this context, the second scenario sounds weird. Friends say hello to friends.

Whenever it comes to user onboarding, a lot of companies don’t even welcome their guests when they sign up for their product. It’s a “help yourself to the kitchen” kind of deal. As a user, it can feel a bit odd. All humans have the innate desire to feel welcome.

In this example by Nimble CRM, they were able to showcase a message from the CEO that personally welcomed the user to the product.

The message simply shares a little bit about why the founder decided to create the product and reinstates the value proposition. This message can also help increase a user’s motivation for using the product.

Key Takeaways

  1. Welcome messages are your opportunity to welcome new users and make them feel invited – you are the host after all.
  2. In addition to saying hello, you can use this as an opportunity to reinstate your value proposition and increase your user’s motivation before diving right into the product.
  3. Welcome messages can also be used to set expectations of what people should expect in their experience using your product.

Product Tours

Ultimately, product tours help put your user on the right track.

In Evernote’s case, this might include trying to understand how you intend to use the product so that they can help you accomplish your goals.

In Wave’s case, they want to understand how you plan to use the tool so that they can guide you to the part of the product that is most relevant to you.

In Drift’s case, they want to learn how you are planning on using the product from the beginning.

Although completely different products, Wave, Evernote and Drift are asking you to identify your main job-to-be-done in the product. Your response to this question can trigger a different onboarding track that is specific to what you want to accomplish. This is not a one-size fits all model.

If you have a simple consumer application, you might be able to get away without using a product tour step, but if you have a complex product with features that accomplish different tasks, a product tour is a must.

To improve adoption, I recommend utilizing “focus mode” where background elements are hidden and the number of choices someone can take is minimal. A great example of this is the Wave product tour below.

One of the reasons product tours are extremely effective is because they leverage Hick’s Law and the Paradox of Choice.

Hick’s Law: Decision time increases with every additional choice.

Paradox of Choice: More choices, less likely to choose.

By eliminating the number of decisions a new user has to make, you increase the likelihood that they will make the right decision.

When structuring your product tour, it’s important to ask yourself these questions:

  1. What is each user trying to accomplish in the product?
  2. What are the first few steps a user needs to take in order to get value out of the product? For example, CrazyEgg, Drift, and HotJar are borderline useless products until you upload javascript on your website. Once you complete this one action, there’s incredible value in each platform but users need to complete the initial step. If you have a must-have step like the javascript example, you should consider covering it in the product tour.

Key Takeaways

  1. Product tours should ask users what they’re trying to accomplish in the product.
  2. Product tours should cover important step(s) that set users up for success using the product.
  3. High-performing product tours can often utilize “focus mode” where all unnecessary elements like the navigation bar are stripped away from the product until the user completes the product tour.
  4. Product tours are typically between 2-5 steps, but can be longer or shorter depending on the complexity of your product.

Progress Bars

When running a marathon, I often look forward to seeing the markers for every kilometer I’ve run so far. Each marker reminds me of how far I’ve run and how far I have to go before the race is over. At first, it can be demotivating when you see that you’ve only run 1 out of 42 kilometers.

However, once you start getting closer to the 30 km mark, your motivation goes up, you push yourself harder and you run until you cross the finish line or, in my case, pass out.

When it comes to user onboarding, the same principle holds true. Humans are addicted to progress and will work hard to finish something they think is achievable.

When first using LinkedIn, we’ll see a progress bar to showcase how far we’ve come along setting up our account. When we see that we’re a beginner, we’re curious what it takes to become an expert and will work through the steps LinkedIn has laid out in order to fully set up an account.

When setting up a Drift account, they use a progress bar to showcase how far you have to go in order to complete the onboarding steps. This reassures people that the onboarding process won’t take long and that you’re only a few steps away from completion.

Key Takeaways

  1. Progress bars that play best to our bias start with a substantial percentage of the bar filled out. This helps us feel like we’re already underway instead of starting from scratch, and it increases our desire to complete the task.

Onboarding Checklists

Checklists have been proven to help us break down big tasks into bite-sized ones.

In Evernote’s case, they use an onboarding checklist to help users set up their account.

Checklists alone can only get you so far. If you want to get the most value out of your onboarding checklists, you’ll want to have them partly filled out by the time the user sees them.

This simple tactic allows you to employ the “endowed progress effect,” which is a psychological phenomenon that basically boils down to this: the closer people think they are to completing something, the more likely they are to actually see it through.

In Quora’s case, once you go through their product tour, you’ll automatically complete 1-3 of the checklist items.

In addition to giving your users an overview of the steps they need to set up their account, you simultaneously increase the user’s motivation because they now know how many steps it takes.

For best results, I recommend having between 3-5 checklist items for a new user to complete.

According to Zapier, another reason why onboarding checklists work so well is because of the Zeigarnik Effect. This phenomenon is based on the tendency to think about uncompleted tasks more than completed tasks.

Basically, not finishing a task or tying up loose ends can be really bothersome, nagging at us until we complete it. Researchers call this task tension. It’s that nagging feeling that helps someone stay the course until they’ve achieved the goal and can relieve that tension.

It’s why cliffhangers are so effective in movies and TV shows. It’s why crossing off an item on your to-do list can feel so satisfying. It’s why this might freak you out.

Key Takeaways

  1. Checklists can motivate new users to complete the crucial setup tasks required to get your product up and running
  2. Checklists can turn complex, multistep processes, such as scheduling out a month of social media content, into simple, achievable tasks
  3. Onboarding checklists work to our advantage because they employ both the Endowed Progress and Zeigarnik Effect

Onboarding Tooltips

Onboarding tooltips can be used to help users learn how to use a product.

Tooltips can reduce the burden on support and scale up usability.

Here are the three main ways you can use hotspots and action-driven tooltips:

  1. To show first-time users how to use the product
  2. To offer helpful tips to new users. Think of this like a coach
  3. To show experienced users new areas of the product they might never have tried otherwise. This is great for increasing the retention of customers

In Drift’s case, they use hotspots effectively to direct new users to explore key areas of the product.

In Slack’s case, they use hotspots to show you how to use the platform quickly. With a product like Slack, where they’re literally training you to communicate in a different way than you’re used to, these hotspots train you quickly on how to use the platform.

One of the benefits of using onboarding tooltips is that they’re relatively easy to setup. However, a lot of companies use onboarding tooltips incorrectly.

Tell me if this sounds familiar? You log in to a product for the first time and then a tooltip pops up and tells you to click on a feature so you do. Then the tooltip prompts you to take you through one feature after another until you’ve explored the entire product.

This abuse of onboarding tooltips is like playing whack-a-mole.

The problem with this approach is that it leads the user to experience no meaningful value in the product.

Contrast the experience I just shared with you to an onboarding tooltip that walked you through how to create your first invoice.

One leads you aimlessly through an entire product, while the other is razer specific on helping you. Now, tell me, how are you going to use onboarding tooltips from here on out?

Empty States

Most software applications are relatively boring when you first log in. There’s no data that is specific to you, it’s just the raw application. So, when you first login to an application, what do you show people? Do you show people dummy data?

Unfortunately, there is no broad stroke answer to this one, but I would suggest against using dummy data in most cases.

What I would recommend is using an empty state to show people what they need to do in order to successfully set up their account and experience meaningful value in the product.

In Gmail’s case, an empty state is used to help the user set up their account. As you can see, each of the items listed in Gmail’s empty state helps users set up and personalize their account.

For Story Chief, they use an empty state to encourage users to craft their first story.

For Buffer, they use an empty state to encourage you to connect your social media accounts. If you think about it, nobody is ever going to use Buffer unless they complete this step. As such, the Buffer team has done a great job ensuring that people connect their social media accounts right from the beginning.

When it comes to deciding what items to include in an empty state, make sure to ask yourself these questions:

  1. What steps do I need in order for a user to experience a quick win in the product?
  2. What mandatory steps are there in my onboarding process?
  3. How can I make sure that the majority of users complete this step?

If you ask yourself those three questions, you’ll have a much better idea of what items you should include in an empty state.

Key Takeaways

  1. Empty states are commonly found when a user hits a product’s dashboard for the first time.
  2. Empty states should prompt people to take an action that will lead them closer to experiencing a quick win and meaningful value in the product.
  3. In-App User Onboarding Tools

When it comes to user onboarding, these are the top in-app onboarding tools:

  • Welcome Messages
  • Product Tours
  • Progress Bars
  • Checklists
  • Onboarding Tooltips
  • Empty States

Each tool can be used to help users experience meaningful value in your product. However, the context in which you use each tool will determine how effective it is.

For instance, using welcome messages on the second visit won’t be nearly as effective as showing users the first time they log in.

Now that we’ve covered the main in-app onboarding tools, let’s dive into conversational onboarding tools and see how they can complement our existing onboarding.

Conversational Onboarding Tools

Conversational Onboarding Tools work to educate users, bring them back into the application, and eventually upgrade their account.

Here are the most common conversational onboarding tools you can use:

  • Lifecycle Emails
  • Push Notifications
  • Explainer Videos
  • Direct Mail

These are some of the main reasons why conversational onboarding tools are becoming widely adopted:

  • It helps educate users
  • You can set the right expectations
  • You can get your users where they are and pull them back into your app.
  • You can work to increase people’s motivation to use and buy your product.

One of the biggest problems conversational onboarding tools address is that far too many people look to tools to solve their problem when, in reality, there’s often an underlying issue why something is not working.

Take going to the gym as an example. If you buy a membership but never touch foot in the gym once, you’re not going to wake up the next day looking like Arnold Schwarzenegger. The gym could help you become more fit, but it’s useless unless you invest the time in using it.

The same concept can be applied to software. We need to make sure that we do our job educating people and setting the right expectations.

One of the best ways to do educate users and set the right expectations is through lifecycle emails.

Lifecycle Emails

In this video below, I’ll share how you can create a just-in-time user onboarding email system that will help you convert free users into paying customers.

The primary function of lifecycle emails is to do something your site can’t: go get your users where they are and pull them back into your app. That’s to say, if your gym members aren’t showing up, lifecycle emails drive out to their house and haul them out of bed on your behalf. That said, the end goal of lifecycle emails is to eventually not need them, in the same way that you don’t permanently install training wheels — the point is to help see the adjustment period through, then let the “real” use take over. For software, that means habitual & unprompted use. To accomplish this, lifecycle emails should be set up to nudge people along through the most critical inflection points of the journey from signup to thriving user. They’re kind of like a joint between two bones, in that sense: acting as the connective tissue that links one key activity to the next. –

When it comes to setting up lifecycle emails, one of the most challenging parts is figuring out what emails you even need to send in the first place.

To make this whole process easy on you, I’ve compiled the top 9 lifecycle emails you should use:

  1. Welcome Emails
  2. Usage Tips
  3. Sales Touches
  4. Usage Reviews
  5. Case Study
  6. Better Life
  7. Post-Trial Survey
  8. Expiry Warning / Trial Extension
  9. Customer Welcome Emails

At their best, lifecycle emails act like an extension of your product with the magical ability to reach beyond your app or site to get people to come back and make progress towards customer happiness.

In this next section, I’m going to break down the ten most common lifecycle emails. To get the most value out of this section, I would recommend crafting a rough draft version of your lifecycle emails while going through each section.

If you need to grab your pencil or laptop, I can wait.

Welcome Email

Welcome emails are triggered as soon as someone signs up for an account. One of the best parts about welcome emails is that it has the highest open rate. Typically you should aim for 60%+ open rates.

Even with my SaaS customer research course, I’m easily able to hit above 70% open rates and I’m no email extraordinaire.

Given that it’s relatively easy to capture people’s attention in a welcome email, what content should you put in it?

Although it’s tempting to write a lot about the product and ask the user to upgrade in a welcome email, I encourage you to not take this approach.

Your welcome emails should only have two purposes. First, you need to train your audience to open your emails. Second, you need to set the expectation of what’s coming next.

To make sure your audience receives this email and it doesn’t get caught in a lovely spam filter, I recommend using “plain text” and no images, at least for the first email.

Lastly, make sure your welcome email has a clear CTA. If you recently launched your product, you can learn a lot from just asking the question, “why did you sign up to use X product?.”

If you’re at a loss for words when it comes to drafting your welcome emails, here are two examples of welcome emails that follow the recommendations above:

Welcome Email One

Subject: a personal hello 🙂



I’m one of the co-founders of [Your Company] and I’m excited
you’ve decided to sign up.

The [Your Company’s Name] Team and I have poured our heart and soul into making [key outcome your product solves for] suck less, so I get really fired up when someone new, like you, joins the ranks.

My top priority is to make sure you’re able to {insert value proposition], so if you have any questions about our product, the website, or even my lackluster
mustache, feel free to reply directly to this email.

I hope you able to [accomplish key outcome in product]! Stay in touch 🙂

P.S. Yes, I’m a real human.

– Wes, Co-Founder

Welcome Email Two

Subject: you’re in — [ company name ]


Hey, thanks again for checking out [ company name ] (we help you [
<5 word summary of what you do ] ).

  • Customer benefit 1 (“You don’t have to worry about X anymore”)
  • Customer benefit 2 (“You can finally actually achieve Y, and in less time”)
  • Customer benefit 3 (“It’s free for the first month” / statement on value received)

But, none of that’s going to happen if you don’t get started 🙂

==> CREATE YOUR FIRST DASHBOARD HERE <== (your action-worded CTA)

Talk soon,


Key Takeaways

  1. Welcome emails have the highest open rates out of all lifecycle emails.
  2. Your welcome emails should only have two purposes. First, you need to train your audience to open your emails. Second, you need to set the expectation of what’s coming next.
  3. To make sure your audience receives this email and it doesn’t get caught in a lovely spam filter, I recommend using “plain text” and no images, at least for the first email.

Usage Tip Emails

Usage tips are helpful nudges that direct users to take steps in the product that will set them up for success.

One thing to keep in mind when using usage tip emails is that you should be careful what activity you encourage. For instance, if the activity you’re encouraging users to take isn’t lined up with experiencing meaningful value in the product, you risk losing the user’s motivation.

In general, your usage tip emails should do these three things:

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

If you can do these three things, you’ll be in a better position to help your users become successful.

A perfect example of a usage tip is from Wistia’s Soapbox product. As soon as I created my first video, they sent a usage tip email to encourage me to share it with someone.

This email helped me learn more about Wistia’s features, but also made it easier for me to experience meaningful value from the product when I eventually shared the video.

Key Takeaways

  1. Usage tip emails nudge users to take steps in the product that will set them up for success.
  2. The best usage tips are trigger-based and sent out once you do or don’t complete a certain item in your onboarding.

Sales Touch Emails

As the name implies, sales touches are when sales reaches out to users. These emails can be automated, but the most important part here is timing.

If you send your sales touch emails too soon, you’ll turn people away. If you send them too late, you’ll miss out on sales.

The sweet spot for sending sales touch emails, ladies and gentlemen, is as soon as someone experiences meaningful value in your product.

As Lincoln Murphy puts it:

“You’ll find in a Free Trial that initial success for your user is actually the point where becoming a paying customer is the next most logical step. So you’ll get that “they convert to a paying customer” outcome you want, by focusing on the outcome they want. Winner-Winner.”

The best time to send out your sales touch emails is as soon as someone experiences meaningful.

For Databox, this is when you create and customize your first dashboard.

Notice how the email doesn’t come across as “salesy” and the goal of the message is to help me get more value out of the platform.

When it comes to your sales touch emails, I’d encourage you to try two things:

  1. Frame your sales touch emails as a “success meeting” to celebrate the user achieving an aha moment and to get more use out of the product
  2. Invite inactive users to an orientation demo (e.g. “30-minute crash course on how to share documents and collaborate between teams”)

You’ll most likely find that these “sales” emails are well received and users will be more than happy to hear what you have to say.

When writing your sales touch emails, provides a few free templates to help you get started. I’ve included one of my favorite sales touch emails below:

Subject: [Intriguing phrase about how a paid feature will make their lives easier. E.g…

Hi {{user.first_name | capitalize | default: “there”}},

[Pain point referenced in subject line] is no fun. [Describe a few problems the pain point causes. E.g., keeps them at the office late in the evening, forces them to delete important files or scatter them across multiple locations, wastes precious hours each week preparing for meetings and then having to reschedule.]

With [paid feature], you’ll [get huge benefit. E.g., have the freedom to take Friday afternoons off, rest easy knowing their files are all in one place, increase productivity by 18%].

Since [paid feature] is part of our [paid plan name] plan, you’ll just want to upgrade to [paid plan name] and you’ll be good to go!

Sounds great. Take me to my Billing page now, so I can start [getting benefit] [link].

Talk soon,


Key Takeaways

  1. The sweet spot for sending sales touch emails is as soon as someone experiences meaningful value in your product.
  2. Craft your sales touch emails in a way where the goal of the message is to help users get more value out of the platform.

Usage Review Emails

Usage review emails showcase the value of your product.

These emails should far outlive your onboarding experience as they remind people why your product is valuable.

Typically these emails showcase your product’s value metrics.

For Mailchimp, this is showcasing the emails you’ve sent.

For Vidyard, this is showcasing who watched your videos and for how long.

For LuckyOrange, a heatmap tool, they send out a daily and weekly report on your website activity and make it extremely easy to dive into user recordings.

For your own product, you may not be able to leverage usage review emails if your product has a long time-to-value. If that’s the case, don’t worry about including usage review emails in your initial user onboarding email flow.

One of the most common mistakes I see most businesses make when it comes to usage review emails is showcasing useless activity. For instance, how many times did you log in? Yes, logging in counts as “activity” but nobody really cares about that genre of activity. We want to know what activity impacted our lives in a positive way.

As a filter for what metrics or data to include in your usage review emails, always make sure that it passes the “what’s in it for me?” test.

With that being said, here’s a usage review email template from that you can modify to your business:

Subject: Your [Product] weekly activity report

Hi {{user.first_name | capitalize | default: “there”}},

[Statement about what they accomplished with your product. E.g…

  • Here’s how many tasks your team accomplished last week
  • Here’s the current status of your proposals (drafted, sent, and accepted)
  • Here’s how many hours of work [Product] saved you last week ]

[Activity section. Rule of thumb: only show activity that will make your user feel accomplished. A good barometer: is it activity they’d feel proud of, or want to show to their boss? If so, it’s probably good activity to show. E.g…

  • Number of new proposals sent
  • Number of new proposals accepted
  • Increased productivity
  • Increased traffic
  • Increased engagement with their content or product
  • Increased sign-ups or revenue ]

Happy [verb your product does]ing!

– Signature

When it comes to your usage review emails, please make sure you don’t send them out before someone has experienced meaningful value in your product.

If you send these emails out too early, your users aren’t going to be able to see the value of your product.

One thing to always consider is how you can make usage review emails more engaging as time goes on.

Sometimes it requires a bit of creativity on your end and other times it can be as simple as asking your users what they’d prefer to receive in these emails.

FullStory does a great job doing this by asking users what user recordings they’d like to receive in their weekly digest email.

Key Takeaways

  1. Usage review emails are used to showcase the value of your product.
  2. Usage review emails should far outlive your onboarding experience as they remind people why your product is valuable.
  3. As a filter for what metrics or data to include in your usage review emails, always make sure that it passes the “what’s in it for me?” test.

Case Study Emails

As Joanna from Copyhackers would say, case studies are great. As long as you tell the story right.

And by “tell the story right,” I mean be a good storyteller:

  • Open with a hook
  • Lure the reader from one line to the next
  • Start in the middle of the action
  • Create compelling characters
  • Set the story around a central conflict

If you don’t have conflict, you don’t have a story.

If you don’t have a hook, who would read?

As Joanna points out in the two variants below, which email does a better job capturing your attention?

Image Credit to

If you’re like most people, Treatment B captured and maintained your attention throughout the entire email and gave you a convincing reason to upgrade.

Part of that reason is because your customers can relate better with your users and often do a much better job selling than you can.

Whether it’s sending a case study email that includes a video testimonial, customer story, or case-study, you need to showcase your customer’s results from using the product.

For Invision, they do this by showcasing some of the incredible designs their customers have created through using the product.

Now, how do you decide which testimonials to showcase?

One of the best ways to decide which testimonials to feature is based on the objections you consistently receive when selling your product.

For most businesses, these objections could be:

  • The price is too high
  • We don’t have the budget
  • It’s not important right now

What I’d recommend doing is pairing your #1 objection with the testimonial that addresses the objection head-on.

For instance, if your top objection is that the price is too high, you’d want to include a testimonial that showcases the amount of value the customer received from using your product.

That way, you’re addressing your top objections head on and your testimonials are doing the heavy lifting for you.

If you send these case study emails before selling each user on your product, you’ll improve your free user to paid conversion rate.

Key Takeaways

  1. Use case study emails to combat objections that your users might have before they enter the buying phase
  2. Make sure that people hear “what’s in it for me?” throughout each case study email

Better Life Emails

Better Life emails focus on communicating the benefits of the product.

The main CTA in these emails will often be to upgrade an account, however, they can also be used to direct people to try specific features out on their own.

Better Life emails are different than case study emails in that it doesn’t rely on you to tell a customer’s story but can simply focus on communicating the benefits of the product.

For Twist, they use Better Life Emails to encourage people to “take back the workday” and sign up their team.

Image credit to

For your Better Life emails, one of the best things you can showcase is how your product will make the user’s life better. If you’re selling a business intelligence tool, this could be showcasing how the user will no longer need to spend countless hours crunching numbers in excel.

One of the most common mistakes whenever it comes to Better Life emails is only focusing on the functional job your product solves for.

To avoid this, you need to go beyond “what” the product is and do customer research. This will help you highlight the emotional and social jobs people hire your product for.

As Steve Blank would say, “Cheating on customer development is like cheating on your parachute packing class”

It’s not worth it. In any purchase, you have to account for the functional, social, and emotional reasons why people buy your product. Here’s a breakdown of each job:

  • Functional Jobs. The core tasks that customers want to get done
  • Emotional Jobs. How customers want to feel or avoid feeling as a result of executing the core functional job
  • Social Jobs. How customers want to be perceived by others

If you can understand these three main reasons why people buy your product, you can boost your conversion rate and ultimately acquire more customers.

If you’re not confident why people buy your product, I’d recommend taking my free customer research course as a start.

Before writing your Better Life Emails, ask yourself these questions:

  • When talking to potential buyers, what benefits get them most excited?
  • What benefits make it a no brainer for people to upgrade?

If you ask yourself these questions, you’ll have a better idea on what benefits to feature.

Key Takeaways

  1. Better Life Emails are used to showcase the benefits of your product
  2. The CTA is often used to upgrade users, however, it can also be used to help users experience those benefits for themselves in the product

Expiry Warning Emails

Expiry warning emails remind the user to upgrade before the free trial ends.

Typically expiry warning emails are used for free trials. Freemium models don’t typically use expiry warning emails because you are giving away part of the product away for free forever. With that being said, if you have a hybrid freemium model where you combine both free trial and freemium models, expiry emails can be used to motivate users to upgrade.

If you have an opt-out free trial (aka when you require the credit card upfront before someone can start the trial), you MUST send expiry warning emails. No ifs or buts here.

If you don’t send out expiry warning emails, you’re guaranteed to annoy users who give your support a hard time and demand a refund.

Can we really blame these people though? What did you do the last time you signed up for a product with a credit card and missed the deadline? Did you continue paying for the product for a month or two before realizing you forgot to cancel? Or did you demand support give you a refund because you forgot to cancel your plan?

Now, I won’t dive into whether you should have a free trial with or without a credit card at signup right now, but, as a general rule of thumb, you should always make it easy for users to cancel their account.

For Squarespace, they send out expiry emails to notify users that their trial is going to expire soon. What’s great about this email is that they reinstate the value proposition and why it makes sense to upgrade now.

According to PostMark App, expiry warning emails have three main goals:

1. To set clear expectations

Trials end – that’s just how they work. However, if users have provided a credit card as part of the signup process, and they’ll be charged automatically, you want to make sure to give them a few days notice about the charge so that they aren’t surprised.

The last thing you want is to annoy users who forgot they signed up for your product and ended up accidentally paying. When they figure out that they were charged, they will demand a refund.

Even if you don’t require a credit card upfront, you want to craft a painless transition to becoming a paying customer.

The best way to do that is by:

  • Giving users as much notice as possible
  • Making sure it’s crystal clear when the trial expires and what happens if the trial expires
  • Providing a call-to-action for users to upgrade

2. Make it easy for users to upgrade, cancel or do nothing

Some people will upgrade, and some won’t. As such, you want it to be easy for people to upgrade. With that being said, you also need to keep in mind that most people won’t upgrade so it should be easy for users to cancel their account. Making this process clear and easy from the expiry email can serve as a great way to make a positive impression. Who knows? Maybe they’ll return someday.

3. Communicate how users can get help

The transition from trial to paying customer can be a stressful one. Once your customers decide to use your software, they’ll want to make sure the transition is seamless. In some cases, they might even wonder if their existing data from the trial will be maintained. When will they be charged? How can they get approval from their team?

There are countless questions and concerns you’ll receive, the important part is to make sure that customers know that they can get help and where to find it.

What are some common mistakes with trial expiration emails?

Trial expiration emails are special because they’re serving two very different user types.

On one hand, you have the people that want to become paying customers, and on the other hand, you have those that don’t. In the same email, it’s important to address the needs of both groups without making the email confusing. Most mistakes in trial expiration emails stem from these conflicting goals.

Mistake #1: Failing to provide enough advanced notice

Weekends, vacations, and travel can interfere with the timing of a trial expiration. So it’s important to give people a heads up. This way users know exactly when a trial will expire and you can help them avoid accidental interruptions like forgetting to cancel their account.

In general, I recommend sending an expiry email at least three days before the end of each user’s trial. This will give your users enough time to make a decision on moving forward with your product or not.

Mistake #2: Assuming that the recipient wants to begin paying for the product

One of the biggest mistakes I see companies make when sending out expiry emails is not including the product’s main value proposition. It should be no surprise that offering a compelling reason to take an action results in more people (actually) taking that action.

Just because someone signs up for a free trial does not mean that they are ready to buy. The majority of people who sign up for your free trial or freemium model won’t convert.

As such, you need to make sure that you include compelling reasons for someone to upgrade their account in your expiry emails.

Screenhero proves this point by failing to include a convincing reason to upgrade.

On the other hand, Squarespace’s expiry email does a great job highlighting the key benefits of the platform. Now we know why we should consider upgrading, right?

To recap, your expiry emails should be able to answer these questions:

  1. Why should I upgrade?
  2. How do I upgrade?
  3. How much time do I have left?
  4. What happens when the trial is over?
  5. How do I cancel? If you require a credit card for your free trial signup.
  6. Where can I go if I need help?

Key Takeaways

  1. You must send expiry emails if you have an opt-out free trial. If you don’t, users will forget they signed up and get mad when they find out they’ve been charged for a product they haven’t been using
  2. Make sure you reinstate your value proposition in each expiry email. If you do, you’ll create a compelling reason for users to upgrade
  3. Make it incredibly easy for someone to upgrade in the expiry email

Customer Welcome Emails

Have you ever purchased a plane ticket on a somewhat sketchy travel website and then waited for what seemed like an eternity to receive an email confirmation that your trip was booked?

When you don’t have a lot of trust in a brand and buy something from them, waiting for an email confirmation email can fill like an eternity. Your new customers feel the same way.

Customer Welcome Emails have three main goals:

  1. You want to reassure your users that they made the right decision
  2. You want to remind your users of what they can now do with the platform
  3. You want to set the expectation for what’s to come next. Is a customer success rep going to reach out?

One thing that is all too common is businesses that don’t have an autoresponder set up to welcome new customers. Most of these businesses do reach out manually but it takes them a long time.

Meanwhile, your new customer is getting nervous sweats and wondering if they made the right decision. Pro tip: don’t make your new customer think twice.

For Spotify, they welcome users as soon as they upgrade to the premium plan.

Image credit to

One thing Spotify has done really well in this email is reminding users why they upgraded and also showcasing the value of the platform. This email increases a user’s motivation to check out the product and listen to some great music without ads.

If you have a freemium product, I’d strongly recommend including a recap of your premium features so that the user can then explore them afterwards.

For Realtime Board, they send out customer welcome emails as soon as you upgrade. What’s great about this email is it’s easy to pay attention to the points that are relevant to you and dive into the product.

Image credit to

Key Takeaways

  1. Customer Welcome Emails must be sent as soon as users upgrade.
  2. The whole point of customer welcome emails is to reassure your users that they made the right decision, remind your users of what they can now do with the platform, and set the expectation for what’s to come next.

Post-Trial Survey Emails

Even if we put together the most amazing free trial experience, the majority of our users are just not going to convert.

Some users might have never been a good fit.

Some might have just not had time to check out your tool.

Others, well, they might just have needed more time or needed someone to help them learn how to use the product.

Although there are countless reasons why people may not have upgraded, you’ll never learn “what stopped them” if you don’t implement post-trial survey emails.

For Autopilot, their post-trial survey emails look like this.

What I like about this email is how it gets straight to the point and encourages you to fill out the quick survey below.

Based on your response in the survey, Autopilot enrolls you into an automated sequence.

Autopilot recommends starting with this list:

  • Still evaluating → Offer a trial extension
  • Not a fit → Drop into nurture
  • Too complex → Schedule a customer success call
  • Too expensive → Provide a one-time discount
  • Went with another solution → Send top of funnel lead nurturing emails to stay top of mind when the other service doesn’t work out
  • Just doing research → Add to nurture (notice the nurturing trend?)
  • Missing product feature or integration → Update your product roadmap, let the expired trialist know when it’s live

If you use your free trial survey in this manner, you’ll undoubtedly be able to handle objections as to why people didn’t buy your product, learn more about how you could improve your free trial experience, and ultimately help more people.

Key Takeaways

  1. Post-trial survey emails can help you improve your free trial to paid conversion rate if you trigger certain events based on the user’s feedback. For instance, if a user says the product was too complex, you can then have a customer success representative reach out to try to walk the user through the product.

Lifecycle Emails Overview

When it comes to user onboarding emails, these are the most common mistakes:

  1. Not outcome-driven
  2. Not tied to what you’ve done in the product
  3. 100% time-based
  4. Feature-driven
  5. One-size fits all

Sound familiar?

The entire experience is devoid of personalization. As a result, this process results in many different forms of waste, such as:

  • Waste of over-producing content
  • Waste of the new users’ time if the content is not relevant
  • Waste of resources driving signups
  • Waste of customer support team’s time
  • Waste of the sales team’s time trying to sell low potential users

Don’t get me wrong, this process can still convert users into paying customers but it misses the mark on meeting the user where they are in their journey.

For a 14-day free trial, here’s what a typical email engagement program looks like:

  1. Day 1 – Welcome Email
  2. Day 3 – Content to Educate User
  3. Day 5 – Check-In Demo
  4. Day 8 – Product Features
  5. Day 12 – Expiry Warning Email

The problem with this approach is it’s one-size-fits-all and doesn’t bode well for the outliers below:

  • If you’re a power user and keep receiving product feature emails for a feature you’ve already used, it’s pointless
  • If you’ve never logged into the product, why should you receive advanced lessons on how to use the product?
  • Or if you already upgraded and continue to receive all the emails, how does that feel?

The only way to avoid these scenarios and improve your free user to paid conversion rate is to use smart signals.

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

Wes Bush
Wes Bush

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
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