How to Increase Paid Subscriptions with Effective SaaS Onboarding Emails

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Here’s a scary fact for SaaS business owners: it doesn’t matter how good your service is – a confusing or ineffective onboarding experience can ruin your business.

That’s not an exaggeration – it really is that important.

I don’t say this to make you panic, though. In fact, the potential upside of a strong onboarding process makes it a huge opportunity for growth. It’s not uncommon to achieve results such as a 71% decrease in churn or 350% higher conversions to a paid subscription by creating a better onboarding sequence.

This post is all about why you need an effective onboarding email sequence – and how to create one.

Why an Engaging Onboarding Experience is Vital

Let’s start with an uncomfortable truth: the majority of your free trial users will login for the first time…and never come back.

This often isn’t because they hated the product. In many cases, at least some of these users could have become loyal subscribers.

So what went wrong?

To understand why this happens, it’s important to be aware of the psychology of free trial users.

When a user signs up for a trial, your marketing has convinced them just enough for them to give you a small amount of their valuable time. That’s it. They are still highly sceptical that your product can deliver real value.

For that reason, they aren’t going to devote hours to learning how to use your software.

Instead, most will login and take a quick look around. If they aren’t engaged – or at least partially convinced of the potential value – they will probably get distracted and do something else.

At this stage, even if they had every intention of coming back and giving your software another try, you’ve probably lost them forever.

Now, an internal onboarding process can help this. But it can’t bring people back once they leave.

And that’s where onboarding emails come in.

The Importance of Email in the Onboarding Process

There are plenty of ways to guide users through the onboarding process. In-built tutorials, checklists and fast support are all important examples.

But SaaS onboarding emails are a vital component. In fact, I rank them as essential.

As I mentioned, free trial users who login and leave may be ideal prospects. They may just have been distracted, didn’t have time to start using the software, or weren’t grabbed by your onboarding process.

Emails allow you to re-engage these users outside of your software. Do this right, and you could greatly increase your conversion rate from free trial to paid subscription.

What Makes an Effective Onboarding Email Campaign?

There are two primary goals of an onboarding campaign:

  1. Get the user to deeply engage with the software and quickly receive value.
  2. Move the user to a paid subscription at the end of a trial.

It sounds simple – and it can be.

But one of the biggest mistakes – and reasons why onboarding fails – is not putting yourself in your customer’s shoes.

When you live and breathe your business and service, you’re in a very different place to a new user. You might know that they need the product. They may even believe that they need the product. But unless you can remove their doubts and fears, only the most motivated free trial users will take the time to learn how to get the most out of your service.

SaaS onboarding emails, when done correctly, can bridge the gap between how you want customers to use your product – and how free trial users actually use it.

Step 1: Define Specific Engagements for a More Invested User

The goal of onboarding is to get users deeply engaged in your product or service.

You don’t want them to fill in basic details (unless those details are vital to getting value from the product). Instead, you want users to take significant steps towards becoming a long-term user.

For that reason, before you start writing SaaS onboarding emails, you need to know the specific engagements you want users to take.

How to Develop an Onboarding Roadmap

Here are a few questions you can ask to develop a “roadmap” of customer engagements:

  • What’s the quickest way I can demonstrate value to the user?
  • What are the most important actions users need to take before they can receive this value?
  • What actions can I get users to take that would make converting to a paid subscriber a logical next step?
  • What do my free trial users want to achieve from the trial?

The last point is key. Take note that the question is not what you want from the free trial (i.e. a paid subscriber) – it’s what your customer wants.

Now, by answering these questions, you’ll probably have a relatively long list of actions your users need to take.

But during an onboarding sequence, we don’t want to bombard users with 15-20 actions. This is likely to have the opposite effect to our goal of increased engagement.

Instead, pick the top 3-5 actions you think are most important for users to take. Then put them in a logical order and try to define a direct or indirect benefit to the user forcompleting the action. These are the “milestones” for your onboarding sequence.

Don’t Forget Promotional Emails

It’s true that effective SaaS onboarding emails naturally increase the chances of a paid subscription. As users become more engaged, they hopefully start to receive real value from your service – increasing the chances of a paid subscription.

But why leave this to chance?

It’s important to include sales messages in your onboarding sequence – especially towards the end of the trial.

Promotional emails should include the following:

  • A reminder that the user’s free trial will expire soon (with exact number of days remaining).
  • A recap of what the user has learned/completed so far.
  • An overview of the benefits and value provided by the service (and how they are linked to completed actions).
  • A call to action to upgrade to a paid subscription.

You can still include educational content in the promotional emails. But the goal is to get the user to subscribe to a paid plan.

I recommend including 2-3 “hard sell” emails during the thirty day trial.

The Goal of Each Email is to Move Users to the Next Step

It’s tempting to try and get users to speed through your onboarding process. While there are advantages to doing this, each email should only ever have one goal.

Read that again – it’s important!

To put it another way, the only purpose of each email is to move each user to the next step in your roadmap.

If each email succeeds in moving the user forward along your roadmap, by the end of the onboarding sequence they will be deeply engaged and, hopefully, have received real value.

This sounds simple in practice. But when you start writing the emails, it’s easy to fall into the trap of asking users for two or even more actions. This is a mistake.

By the way, asking users to like your Facebook page or follow you on Twitter is still asking for an action. So these goals should be addressed in separate emails – as long as you think they are important.

Note: In this post I’m only discussing timed emails. These are sent out automatically on a fixed schedule regardless of user action. Timed emails are a good start, and can greatly improve free trial upgrade rates. But you’ll probably want to incorporate behavioural emails (i.e. emails that are triggered based on actions) into your strategy. Look out for a future post about behavioural emails.

Step 2: Write Personal Emails

Once your roadmap is in place, it’s time to write the emails.

The success of SaaS onboarding emails often comes down to how well you understand your customers. What are their fears? Objections? Beliefs about yours or similar services?

Your users desires, in particular, are often not as simple as you think. So it’s vital to fully understand your prospects and then write emails that put them at ease…while focusing on the benefits of completing the desired action.

Here are a few more tips for writing engaging emails:

Use a Personal Tone

Email is a personal channel. So make sure your emails are written directly to the reader.

An easy way to do this is to imagine you’re writing to a single customer. Even though the email will be sent to thousands of users, it should feel like one-to-one communication.

Also, try to avoid being too formal in the email (unless your target audience prefers this type of communication). The emails should be easy to read – otherwise they are likely to be skipped.

Don’t Overdo Personalisation

The occasional personalised greeting can have a positive effect on your emails. I use “Dear [firstname]” for many of the onboarding emails I write for clients. But don’t overdo it.

If you continuously add the user’s name throughout the email, it comes across as patronising. The days of users being impressed by this type of blatant personalisation are long gone.

Avoid Being Overly “Cute”

There’s nothing wrong with writing “cute” emails – as long as the tone doesn’t get in the way of the message. Unfortunately, many SaaS providers focus so much on tone that the message becomes lost.

To be clear: you want the emails to be personal. And you definitely don’t want them to be dry or boring.

But if your tone starts to become the focus of the email, it can start to detract from the benefits and goals you are trying to convey.

Note: I offer a SaaS onboarding copywriting service. If you want to hire a professional to write your emails, contact me to see how I can help.

Step 3: Ask for a Specific Action

As you know, each email should only have one goal. Correspondingly, there should only be one CTA in an email.

This doesn’t mean you can’t have two buttons or links. In fact, I often put two or even three links in an email so users never have to search for where to click. But these links should all lead to the same destination.

Here are a few tips for getting the user to take action with an effective CTA:

  • Make sure your CTA is easy to find. Both buttons and text links can work. Just make sure that you use colour and other formatting to make the CTA stand out.
  • Use an accurate call to action. The text you use for your CTA should accurately describe where a user is going to be sent. If you can include an implied benefit in the CTA – even better!
  • Link to the exact location. If you want users to perform an action, don’t link to their control panel homepage. Instead, link directly to the page within your service. You can go one step further and use a one-time authentication key to log users in automatically when they click the CTA.

Step 4: Track Your Results and Iterate

Once you’ve implemented your initial onboarding strategy, the next step is to improve it.

For this reason, every email, link and goal should be tracked. You should be able to view granular stats for each email – including open rates, click-through rates and actions completed.

While stats such as open rates are important, you should only optimise based on how effective an email is at getting users to take the desired action.


Getting a user to sign up for your trial isn’t the end of the hard work – it’s just the beginning. You’ve managed to get their attention, but now you need to show them value.

Creating a set of engaging, persuasive emails is an excellent way to move users through your onboarding roadmap. By writing in a personal tone, assigning one goal to each email, and making it easy for users to take small steps towards real value, you can encourage deep engagement. This nearly always results in greater conversion rates to paid subscriptions.

Then, once you’ve gathered data on which aspects of your onboarding sequence is effective – or not – it’s important to use this data to continuously improve.

Is your current onboarding process not generating the results you need? Contact me today to find out how my SaaS copywriting service can help boost your conversion rates from free trial to paid subscribers.

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