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[Webinar] User Onboarding Emails — Examples & Best Practices

In this webinar that we hosted with the awesome team at Userpilot, I’m sharing some of the best practices for crafting onboarding emails that convert trial users to paying customers.

Watch the webinar if you want to learn:

  • What are some of the most effective types of user onboarding emails that improve the trial Conversion Rate. With real examples from Encharge customers and other successful SaaS companies.
  • Answers to the most pressing onboarding questions that SaaS businesses in the audience had. Like “how to figure out my critical value moments if I have a complex tool?” or “what is the perfect trial length?

You can watch the full webinar recording and check the slides, as well as a lightly edited transcription of the talk.

Full Webinar Recording

Webinar Slides

Webinar Transcript

[00:00:04.710] – Aazar

Hi guys, this is Aazar. I’m the Head of Growth at Userpilot. Thank you for joining us. I will give the reins to Kalo and so that he can start presenting. Kalo, would you like to introduce yourself?

[00:00:17.980] – Kalo

Yeah, absolutely. A pleasure to be with all the fine folks here and hope the weather is as good as here. It’s sunny in Sofia, Bulgaria, today. So I am the co-founder of Encharge is a marketing automation platform. We help SaaS companies convert more of their free users — trial or freemium users — to paying customers through targeted emails. And we mostly focus on the so-called action-based emails or trigger-based emails. And that’s what this presentation will be primarily on today.

[00:01:10.890]- Aazar

Before we start, let me ask our audience a question about onboarding. How do you currently do email onboarding? How many of you send time-based, and how many of you send trigger-based emails?


Great. So we have some data, and it says 50/50 for time-based vs. action-based emails in our audience. You can start with the presentation now.

[00:02:32.450] – Kalo

Again, we’re going to talk about user onboarding emails and some examples and best practices.


At Encharge, we primarily help SaaS companies convert more trial users through targeted action-driven emails to increase.

In this presentation, we’ll cover a few main things.


First of all, I’ll show you some examples. Example triggered emails from some of our customers, as well as some great successful SaaS companies.


Then, we’re going to talk about how actually to identify these actions in your app. What are the actions that you want to send emails about?


Towards the end of the presentation, I will give you a real-life example of marketing automation flow from one of our customers. That way, you can see how these emails are implemented and how you can implement them for your product as well.

Action-triggered emails = higher trial Conversion Rate


In the beginning poll, some people answered that they have no idea what trigger-based emails are.


In a nutshell, these are emails that you send when the user does do or doesn’t do something in your app. Let’s say you have a product like Encharge, where the main benefit is sending emails. You’d want to send a trigger-based email when the user imports their contacts, creates their first campaign or invites a team member. These are the action-triggered emails.


These emails are the bread and butter of SaaS onboarding. They’re much more effective than time-based emails and lead to higher conversion rates, but are also much harder to execute.


The majority of your trials will leave your website after they sign up. They would visit a page or two and leave your product forever. The only way to get people back to your website and push them down your onboarding process is to use emails.

And the best type of emails you can use when it comes to SaaS is the action-based email.


Action-based emails work in pace with the customer journey and get higher engagement for that reason. The user receives an email when they care about that email. When they activate a feature, or they’ve started activating a feature, but haven’t completed the whole process. In that case, for example, you can send the push or nudge email.


These emails take into consideration the journey of the user. Bear in mind that there will be some people that are really at the top of your funnel — they’re just evaluating tools. For those people, you don’t want to send like very advanced how-to guides or anything like that.


But there will be some people that are already familiar with the features; they have activated a particular set of important features. For the people that have already experienced value in your product, you want to send them, for example, an upgrade email where you can push them to come back to your app and make a purchase.


An important thing to consider here if you’re sending time-based emails is that most time-based emails would not be relevant for your users. For example, let’s say I sign up for your task management app, and I complete a few tasks in your app. And a couple of days later, you send me an email that prompts me to go back to the app and complete my first task. This will be an irrelevant email to me.


But the biggest issue here is that one irrelevant email would leave a bad taste in my onboarding experience, and I would perceive the whole email communication is irrelevant from that point onward. This dampens the entire onboarding and reduces email engagement.


It’s not just about sending one irrelevant email, it’s the whole experience and how your users perceive the relevance of your communication.

Onboarding emails that improve Conversion Rate


We have found with our customers there is a set of emails that you want to send, and this pretty much applies to all free trial and freemium SaaS products.


The first one is the welcome email, which you send when your users sign up.


You would also want to send reward emails. These are emails that you send when the user activates a feature or does a specific activity in your app. With reward emails, you encourage people for their actions.


Then the Nudge email is something you would want to send when a user has started doing something in your app but hasn’t completed the whole process. You want to get them back on track, back in the app to complete the action.


For the active users, engaged with your app, and experienced value within your app. They had a few features activated, maybe reach that so-called Aha moments. You want to send an upgrade email and don’t wait until the trial expiration date to send out an upgrade email.


And conversely, for the inactive ones, the passive users that haven’t engaged with your app, you will want to offer them an extension, and you will do that through an extension email.


Then we have the trial expiration email, which is towards the end of your trial and then a post-trial expiration feedback email.


In the next few slides, I’m going to explore each type of email with examples from some of our customers as well as successful SaaS companies.

Welcome Email


The first email that pretty much every SaaS company sends is the welcome email message. This is something you want to send on signup. And this is the most engaged email. You could expect anything between 40 to 60% open rate. And the natural thing that most marketers do here is they try to include every single feature, every single call to action resource, webinar, how-to guide, whatever. Because like that’s the first and most engaged email


So we got to make sure it works. We got to put more things into it.


My approach is a little bit different, not only with the welcome email but with emails in general.


I like to keep onboarding emails clear and simple.


Every single email I sent needs to have one business goal. What do you want to achieve with that email? Do you want to get the user back to the app?


Do you want to get feedback? You want them to read the blog post or learn more about your tool, whatever. There’s one single business goal for you.


The next thing is also to consider the user’s desired outcome. So what they want to achieve? This really ties in with the value proposition of your product. So if you have an app like Todoist or task management software, your users might want to save time or improve their communication with their team members and so on.


So once you know your business goal and the goal of the user, their desired outcome, what they are trying to achieve through your software is really easy to then create simple emails with a single call to action.


It depends on how you want to structure your flows. Still, I encourage you if you’re not sure what to include in the welcome email, just explain the main benefit of the software. Explain how the software works in just three steps, and also gives some indication of what the users will expect from the trials or how long the trial is going to work, what features are available, accessible in the trial, and so on.


The next thing is really that single call to action, which is to encourage the next critical action in your app. So in the case of Todoist, that might be creating your first task.


This example is from one of our customers Veremark. They are an HR reference software. You can see the intro from the co-founder. You can see what the benefits are, they’ve quantified the benefit of the software, which is 33 percent faster checking compared to traditional reference checking methods.

Screenshot 2020 04 13 at 2.13.49 PM


They’ve also explained how the software works in just a few steps. They provide us information about the trial. So how long the trial is and what they can expect from the trial. And then, you can see the next critical action – get the user to create their first reference check. We don’t give them links to webinars, help docs, and explain every single feature we have. We just provide one single CTA that gets the user back to the app and gets them to create their first reference check.

Reward email


The next example is the Reward email. The reward email is something you want to send when a user does a specific activity in your app successfully. Whether they invite a team member, create their first task, create their first email. These are little treats that you send in your user’s inbox to make them move towards their desired outcome. We want to encourage here only the things that are critical for them to experience that outcome. So whether that’s saving time or, in the case of Veremark, do faster reference checking. You really want to encourage only those actions that provide value.


You don’t want to send a reward email for every single feature because that’s going to be overwhelming. And we’ll again dampen the whole onboarding experience.


Here you can see the reward email from Wistia, which is pretty awesome. When you create your first video, they send this funky illustration. Another important thing to consider with that email, you want to show them better ways to use that feature. This is again, moving people towards the desired outcome. In the case of Wistia, they congratulated me on uploading my first video. But they’ve also given me the opportunity to customize the video with a thumbnail and colors. I can continue my onboarding experience.

9da16626 9a7b 4a2d 9c78 51070aa3c756 1

Nudge email


The next one, which is a powerful email, is for the people that have started doing something important in your app but haven’t completed it. The goal of the push or nudge email is to get those people back to the app. You want to give them a reason, explain why they need to do that, why they should spend five, ten, fifteen minutes to complete that action. In the Veremark example, they’ve handled one of the objections that background checks are no fun, and they’ve also emphasized the problem of the traditional reference check methods that they do take too long.


Veremark also gives them a reason on why they need to go back to the app and submit that request. And again, you can see here it’s following the same model of just one goal — Get users back to the app to complete the first reference check, one desired outcome — improve their reference check process, and one single call to action that gets people back to the app.

Image 2020 03 04 at 11.13.09 AM 1

Upgrade email


The next one is the Upgrade email. Based on my experience, most SaaS companies send that email when users have reached the end of the trial period. But the thing here is that these emails only work well with activated trials. When a person has completed one, two, or maybe all of the critical actions in your onboarding process, there is no reason not to send them the upgrade email.


And it works the other way around for someone that hasn’t activated any features or reached any value moments. There is no reason to send him on a great email. It’s like asking a stranger in the street to marry you. It would be just very awkward, maybe even annoying for them.


Again, the upgrade email is what you want to send to activated user trials.


You can see a brilliant example here from Zapier. They emphasize what the user will miss out by not upgrading; they quantify the value that they experience within the trial window — the user has automated, 63 tasks, and they are also giving you a little bit more information about their premium plans. It can also see that single call to action. They’ve also made it very relevant for us by offering the most appropriate plan. In that case, the basic plan.

Screenshot 2020 04 07 at 9.56.43 AM 2


You want to contrast the outcomes of upgrading versus not upgrading. You want to picture how your app has improved their life already and how their life will look without the app.


In that, I’ve already automated so many tasks, and by no upgrading, that means that I would not have automated that many tasks.

Extension email


The next email which we want to send to all these people that haven’t done anything in our app. We don’t want to send an upgrade email again.


Instead, what you want to do is start a conversation with those people. You want to allow them to trial your product a little bit longer; you want to engage with them. This will give an opportunity not only to qualify them and see if they’re an actual lead by engaging in a personal conversation with them but also an opportunity for them to help them experience evaluating a trial window. This is a great example from Flow. It’s a very simple email that offers to extend the trial of the user by just replying to the email.

trial extension retention email design from flow 1

Segment active/passive users


The important thing here is that when you send onboarding emails, and when it comes specifically to the upgrade and extension emails, you really want to segment the active users from the passive ones. This is how a flow here would look in Encharge where the user has signed up. We’ve segmented the different types of users — active and passive users. We send the upgrade emails to the active users and the trial extension email to the passive user.

Screenshot 2020 03 31 at 6.33.26 PM 1

Trial expiration email


Trial expiration email is something you want to send at the end of a trial. The goal of the trial expiration email is not to educate the user or help them experience value. It’s the last hit. If onboarding was a boxing match, then the trial expiration email is the final blow. It’s the email that closes the deal.


Here you address any remaining objections — whether that’s the price risk, trust, no urgency. You want to handle this objection. For the engaged users, you also want to provide pricing details and upgrade instructions.


It’s also important to give users options. If you have a premium product, you might want to provide them with an option to downgrade. If they’re not ready to upgrade it yet, give them an extension option.


You can see here the example with Basecamp, where they’ve given the options to cancel or downgrade. They’ve also handled objections like how long it would take to upgrade and what happens with my data.

basecamp 1

Post-trial expiration email


The last email that I want to give you as an example is the post-trial expiration feedback email. You want to send this email three to seven days or maybe 14 days after expiration to all of the users that haven’t upgraded.


The goal of this email is to figure out why people are not upgrading. And you can use that data throughout your whole email communication from the very first welcome email until the upgrade email where you tend to address objections.


The best way we have found to execute the post-expiration feedback email is not to send the link to an external service, but to do something else instead. You want to give your users options. Give them links in that email and ask them to answer by clicking on the single most relevant answer for them.

Screenshot 2020 04 01 at 5.51.03 PM 1


A platform like Encharge would record these clicks, and you can go back to the platform and see how many people have clicked on a specific answer.


This approach actually generates much higher response vs. asking people to open a browser window with a Google form and type in their name and email because it’s so frictionless. All they need to do is click on a link, and their answer is recorded.


Just take the 3 to 5 most common objections and include them in that email. If you don’t have any data, just use whatever your gut feeling says about why people are not converting, and you can include them in that post-expiration feedback.

Onboarding emails in practice


All these emails are great, but how do you set it up in your product? What are the actual steps to execute these emails?


So I’ve broken down the process into three main steps. The first one is for you to figure out what are the critical activities that you want to track in order to send emails around them.


Don’t start with five, ten, hundred. Just start with the three main ones. These are activities that every single customer has completed within their trial window in the past. If you already have any data, you can look at your database, or if you’re more sophisticated and use something like Mixpanel, you can see whether there’s any usage pattern. What are these activities, these actions, that every single customer has completed? So these are the things that you want to push people to do in order for them to reach the Aha moment and experience value.


Once you know these three actions, what you want to do is create an event tracking plan. An event tracking plan is something that you send to your developers. You can use Segment, or they can integrate that directly with the marketing automation tool. You go to developers, and you say, these are the three actions that I want to use with our marketing automation tool. I want to send emails with those actions. Could you please integrate that with Segment or you can look at the API of the marketing automation tool. Then your developers will go back and integrate those. It might take a couple of days or a couple of weeks. Some developers find it very hard to find time for marketing development. You need to be a little bit pushy with them.


The third step is once you have the event integrated with Segment, you want to build a marketing automation flow in your tool of choice.


And now, I’ll show you here how a marketing automation flow works in our platform Encharge. Encharge is a visual drag and drop platform. I’ve already created this flow here for Veremark so that I can give you an example. It works with Triggers and Actions. Trigger are steps that start a flow, and you want to initiate a flow with the events that you mapped in the previous step.

Screenshot 2020 04 09 at 4.39.16 PM 1


Like “Signed up.” This is the event, the name of the event, to have the trigger signed up. You want to send a welcome email. And these are examples that we already covered in the previous slides.


This is a trigger. And then this is the action. And what I did here with that behavior-based flow, once we sent a welcome email, I check if people have completed the next critical action. In the case of Veremark, you want people to send their first request and complete a request (request criteria met). So here I’m using these tags to check if people have completed that specific action. I’m checking if people have sent their first request if they haven’t sent their first request, what I’m doing is I’m sending a push email.


One of the emails that we covered in the previous slides, and try to get people back to the app and get them to complete that action. But if they’ve already completed that action, I’m not going to send that email. What I’m doing then is I’m continuing the flow and checking for the next critical action. If they haven’t completed that action either, I’m going to send them another push email. BUT if they have completed the action, I’m going to send them an upgrade email right away. I’m not waiting 14 days for them to finish their trial.


So if they have completed all of the actions — sent a request and completed a request, it means they have completed all of the critical value moments in my app. It means it’s totally fine for me to send an Upgrade email.

More resources on onboarding emails

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