How to craft email onboarding that converts sceptical free trial users

Email onboarding is your most important channel for converting free trial users into paying customers.

email onboarding free trial users

How many of your free trial users convert to paid customers? The number could be 20% or 25% or 11%, or maybe lower. Wherever your number is at currently, there’s a good chance that email onboarding is your secret weapon to converting more free trial users.

Successful email onboarding requires the right strategy, copy, design, and automation. Plus, continued testing is needed to make incremental improvements.

Keep reading to learn more, and be sure to sign up for GoSquared, so you can get access to free Analytics, free Live Chat and be among the first to hear about our upcoming automation product!

What is email onboarding?

what is email onboarding

Email onboarding is helping new users or customers onboard to your product via email, so that they experience the product’s value sooner and are more likely to convert to a paid customer or to keep their subscription active.

Email onboarding has a lot of uses: everything from onboarding clients for a service to onboarding new employees.

In this post, we’re focusing on using email onboarding to convert free trial users.

Remember: we are about to launch GoSquared Automation where you will be able to put all the lessons from this post into action. Reach out to us if you’d like to be one of the first to try it out!

Email onboarding strategy

email onboarding strategy

The most important requirement of your email onboarding flow is that it guides users to the “Aha!” moment faster, or the moment at which users first experience value and see that your product is worth the cost.

Discover your real “Aha!” moment with customer survey questions and user testing

Your “Aha!” moment might not be what you think it is, and that’s fine.

Start with a hypothesis and go from there. Here are some examples of hypotheses:

  • Our product’s “Aha!” moment is when a user adds a task to a team calendar
  • Our product’s “Aha!” moment is when a user listens to an audio track for at least 5 minutes
  • Our product’s “Aha!” moment is when a user finds at least one prospect’s email address

Because your email onboarding focuses on this “Aha!” moment over all other features and functions, you first need to be sure you’re guiding users to the right thing.

There are two smart ways to test whether your hypothesis is true or not before proceeding with creating or upgrading your email onboarding: user testing and customer surveys.

user testing onboarding emails

You can use a tool like UserTesting to record real user sessions and ask questions on their journey.
For the most valuable information, you should analyze sessions from new users. You can offer an extended free trial (6 months or more) in exchange for the person’s time.

Customer surveys are also useful in validating your “Aha!” moment. These are the top questions (learned from Claire Suellentrop) that will help you understand why users convert (send them to all of your users or an active subset):

  1. How did you discover PRODUCT NAME and what made you decide to try it?
  2. What happened when you first tried PRODUCT NAME that you made you convinced it could help you OUTCOME?
  3. Why did you decide to become a customer of PRODUCT NAME?
  4. What tasks can you achieve with PRODUCT NAME?
  5. How were you handling all of these tasks before?
  6. What feature(s) of PRODUCT NAME could you not live without?

By getting real user feedback from both new users and paying users you can discover the first time your product shows value, and make that the highlight of your onboarding.

Remember: your email onboarding doesn’t need to guide users to every type of value they can receive from the product, but instead the biggest, best, most immediate value.

Email onboarding copy and design

email onboarding design and copy

Now that you know what you need to guide users towards, it’s time to perfect your actual emails.

Should your emails be designed or plain text only?

Entrepreneurs and product marketers ask this question often: should we use designed emails or plain text emails? There’s no right or wrong answer, but there are some important distinctions that can help you decide.

  • Designed emails: Best for product-focused emails like guiding people back to the product, signing in and using a feature because they can be designed in a way that feels like your product
  • Plain text emails: Best for sales follow-up or asking for feedback because they feel more like a personal email, even when automated

plain text onboarding email

In this example of a plain text email, the Head of Product at Alexa (Amazon’s SEO tool) asks for feedback on why the new user has signed up in the first place.

Onboarding welcome email template

Getting the first email right is critical. The longer that new free trial users wait to use your product, the less likely they are to log back in and later convert. You want them to use the product while the memory of signing up is still fresh.

primsleur onboarding email
primsleur onboarding email
primsleur onboarding email

In this example from Pimsleur (language learning app), a new free trial user is given an initial email that thanks them for their order. Payment will begin 7 days later, so framing it as an order helps remind them of that.
Then the email follows up with the steps they want users to take, as well as the free resources.

Here’s the template for recreating this email:

Thank you for your order
Hi {Firstname},
Thank you for subscribing to {Product}! Your subscription is active and ready for you to begin enjoying {Outcome}.
{Order details only if a credit card was required}
Here’s how to get started:
{2 or 3 steps to guide users to the “Aha!” moment quickly}
{Resource 1, such as a device they can use}
{Resource 2, a learning guide like an ebook or webinar}

And here’s a great resource for more customer onboarding templates.

Onboarding email subject lines

To convert more free trial users into customers with email, you need them to open your emails. Test a variety of email subject line styles, including very short, conversational ones and more informative ones.

Here are some examples:

  • A reminder about your invitation to monday.com – Monday.com
  • Hey {Firstname}, How’s Your Business Doing? – FreshBooks
  • Your Secret Weapon to Small Business Success – FreshBooks
  • How to stay above water in your social inbox – Sprout Social
  • Reports that make you look good – Sprout Social
  • Followup… – Sprout Social
  • quick question – Alexa
  • Hi {Firstname}, thanks for signing up! – Alexa
  • Hi {Firstname}, what is your first impression? – Alexa

Copywriting formulas can help you nail your subject lines with no guesswork.

Email onboarding automation

email automation

How you’ll automate your email onboarding dictates much of what you’ll be writing and designing as well.

Long term, you should shoot for email onboarding that relies at least in part on user behaviour. However, setting up trigger-based email onboarding can be a massive project. You might not be able to invest in it right now. If that’s the case then a drip campaign sent to all free trial users is your best starting point.

Remember: we are about to launch GoSquared Automation where you will be able to put all the lessons from this post into action. Reach out to us if you’d like to be one of the first to try it out!

Drip campaign for all users

Sending a drip campaign to all users means that everyone will receive the same email onboarding sequence regardless of their activity inside of the product. Even if you later have some behaviour-based onboarding emails, you will still likely have a drip campaign for one to three initial emails. Welcome emails, as well as emails that share resources (such as help centres ebooks and webinars), can all be set as a drip.

Even though Alexa later makes use of behaviour emails, their initial welcome and sales follow up emails are set as a drip.

Alexa email onboarding

Triggered by user behavior (or lack thereof)

Email onboarding that is based on user behaviour has the opportunity for greater success because it is catering the tips, tricks and advice to what the user is most likely to need. Here are four categories of users that can set-up specific emails for during your free trial:

  • Actively logging in and using high-value features in the app
  • Logging into the app but not using high-value features
  • Hasn’t logged into the app in a certain amount of days during free-trial
  • Hasn’t logged into the app at all during the free trial

Someone who has logged into your app 10 times during your free trial is going to need a different message than someone who hasn’t logged in at all. For the active free trial user, you’ll want to guide them deeper into the product and to an additional value beyond the “Aha!” moment.

For the inactive user, you’ll still be guiding them to the “Aha!” moment, though later in your sequence you may try a different avenue, such as offering a personal onboarding call or sending them different help desk articles.

In the below example from Alexa, a notification email for a site audit (sent during the free trial) is used to offer an ebook.

Alexa ebook offer onboarding email

The lesson here is that all sorts of product-based actions can be used to deepen the onboarding experience. If your product sends notifications when report downloads are ready, or for anything else, you can make use of this precious attention to guide the free trial user to a new resource or feature.

Email onboarding optimisation

email optimisation

Beyond the strategy, the copy, the design and automation, there’s still one more facet on email onboarding to master: optimisation.

Social media tool Sprout Social sends both sales follow up emails and product emails that teach free trial subscribers about new features in a pre-set sequence. They can continually test and optimize these individual sequences and also test them against each other. What gets better results?

onboarding email

email onboarding

Here are all of the factors that you’ll want to test over time:

  • Click through from email through to log in / product use
  • Emails that brought the highest and lowest amount of product use
  • Email subject lines
  • Featured resources inside of emails
  • Steps to the “Aha!” moment
  • Different “Aha!” moments and features (in the case of more complex products)
  • Email design style

Take the time to get your email onboarding right

email automation timing

Email onboarding is easy to overlook when your team is busy building new features and acquiring new users. But everyone who has signed up for a free trial could become a product-qualified lead or even a customer.

When it comes to email onboarding, the ultimate question you need to ask is this: How can I show up in free trial users’ inbox to guide them toward the value they requested by first signing up?

If that still feels mysterious, start back at square one with user testing and customer research. They’ll tell you what they need.