How to Use Webinars to Improve Trial-to-Paid Conversions

we’re now converting over 50% of our webinar attendees (who are our trial customers) into paying ones, improving our trial-to-paid conversions by over 4%, and reducing our churn by 2% as well.
Webinar free to paid trial

We knew we had the best product in the market. Userpilot is one of the easiest user onboarding tools to use. People love our UI.

Yet even with great content and engaging user onboarding flows inside our product, a lot of our trial users weren’t converting.

We were puzzled.

We went back and forth in order to find out why it was happening.

Then it hit us.

While talking with our users, we realized they asked a lot of non-product related questions.

Furthermore, we saw that in order to get high-quality users who will stick with us for the long term, we needed to educate them.

So, we decided to use webinars as our go-to strategy for improving trial-to-paid conversions.

As a result, we’re now converting over 50% of our webinar attendees (who are our trial customers) into paying ones, improving our trial-to-paid conversions by over 4%, and reducing our churn by 2% as well.

Let’s break down our entire process to get to that point.

Understand Where Your Problem Is

The first and probably most obvious step is to identify the problems.

If you’re not converting enough people, what could be the cause? Is it bad user onboarding? Poor feature adoption flows? Poor customer support?

There may be many reasons for this. For example:

  • Your UI may be bad
  • Your users don’t have a serious enough problem
  • Your users are not educated enough about either your product or your solution

In our case, it was the last reason. How did we discover that?

We actually went out and talked to our users.

Webinars to improve Trial-to-Paid conversions

Many businesses these days underestimate the power of one-on-one conversations with their potential users.

For us, it wasn’t a big deal to reach out and schedule a meeting with customers since we’re often manually onboarding them with 2–3 calls before they become paying customers — especially prospects with potentially high annual customer value.

Conversation is also helpful even if the problem doesn’t lie in customer education.

For example, if your UI isn’t intuitive, you can easily reach out to your target audience and ask where the problem is, as well as use some behavior analytics tools like Hotjar that will give you this type of information (you can view session recordings in them). 

No matter what the problem is, the first step is always reaching out to your trial customers and speaking with them.

You have nothing to lose, and you will be able to find out the topics that interest them.


Choose a Webinar Infrastructure that Works for You

Choosing the perfect webinar infrastructure is as important as creating quality content for your webinars.

Here’s the toolkit that helped us create, distribute, and host frictionless webinars:

  • Our tool Userpilot, used to distribute our upcoming webinars to trial users via in-app slideouts
  • Our internal tool, used to distributing our webinars through email (welcome email + webinar specific email)
  • Demio, used to hosting webinars
  • Notion, used to track webinar results and keep everything in one place

Once you know where the problem lies and you sort out your infrastructure, it’s the right time to distribute your webinars.

Here’s a breakdown of how we do it at Userpilot.

How We Distribute Our Webinars

The target audience for these webinars is our trial users who are still evaluating us and trying to figure out the application.

There are two places where we can find them:

  • Inside our product
  • In our email list

So, we have two main ways of distributing our webinars.

Once we identify in-app that our trial users are struggling (whether that’s because they don’t know how to use our product or they get bad results), we show them a slideout with a webinar invitation:

Userpilot Slide out for webinar invitations

Why is this slideout great?

  • It’s triggered when our users need it the most – Since our webinar is about implementing Userpilot’s features and working with our trial customers on their own user onboarding flows, this webinar is sent right on time. Why? Because it’s shown to our trial customers who are currently trying to create experiences for themselves.
  • It’s personalized – There’s nothing worse than having generic in-app pop-ups and slideouts. This particular slideout is personalized with users’ first names, which attracts their attention.
  • It’s “humanized” – The main purpose here is for our users to engage with our customer success manager. Instead of showing various graphics and creatives, we show a smiley face of our customer success manager. Also, in the first paragraph of the copy, she introduces herself. This helps us to create a stronger bond with our trial users.
  • The copy is short, sharp, and to the point – We use different “power words” to make this slideout copy outstanding, such as, What will you learn?, get an instant value out of Userpilot, and so on.

This particular slideout was seen by 1,333 people, and 14% of them signed up, which is a great conversion rate (compared to much lower conversions from email).

Userpilot Slide out conversion rate

If somehow our trial customers forget or overlook our slideout, we also distribute our webinar inside the in-app resource widget:

Userpilot resource widget for webinars

In either case, once the customers click on “Register,” they’re automatically redirected to our Demio landing page where they can save the spot.

Since the landing page is a second step of this flywheel, it’s pretty important for it to be great and converting.

Our Demio landing page is divided into two parts:

  • The first one is the quick and frictionless sign-up for trial users who are convinced our webinar will help them.
  • The second one goes more in-depth into what the webinar is all about.

The first one has an engaging headline and a frictionless sign-up form:

Userpilot Registration form on Demio

Note that whenever you want to get more people on the top of your funnel, webinars, or any other lead qualification magnets, it’s a good practice to use frictionless sign-up forms.

Frictionless sign-up forms are those that don’t require your potential leads and customers to fill in numerous data points. Even more, the sign-up process is quick, easy, and enjoyable.

Now, for the users who are still not convinced that our webinar is great for them, we have the second part of our landing page:

Webinar Details on Demio

Pay close attention to the copy itself. It doesn’t speak on “why our webinar is great.” It actually talks about how people can benefit from it.

Show the Aha moment quickly and reduce the time to value; Boost feature engagement; Onboard new signups,and other bullet points are actually the biggest pain problems that we are solving.

The best part is, the majority of our trial users actually signed up for the Userpilot trial in order to solve these problems.

That’s why, at the end of the day, they click on the “Register” button.

So, we saw how we distribute our webinars across our product. But how do we use emails for it?

When it comes to the emails, as soon as our customers sign up for the product, we send them this transactional email:

Userpilot transactional email

Why is this email great?

  • It’s short, smart, and straight to the point.
  • Webinar sign-up is frictionless.
  • Showcasing a video of our customer success manager, Elise, brings a human touch and helps to build a relationship with our trial customers.

Then, 30 minutes before the webinar starts, Demio sends an automated reminder to our attendees.

These two distribution tactics help us to secure over 30 high-quality trial users to attend our webinars.

Perhaps you think 30 companies is not much, but considering we have quite a big lifetime customer value (LCV), it’s great.

👉 Editor’s note: If you’d like to improve your trial to paid conversion, register for this product adoption school for free.

What Do Our Webinars Look Like?

The main goal of our webinars is to familiarize trial users with our core features and show how to implement them into their own strategies and user onboarding flows.

There are essentially three parts to our webinars:

  • Introduction and asking a couple of questions so we can personalize the second half of the webinars to our users’ needs
  • A short, quick breakdown of Userpilot and showcasing how it works
  • Educating the people on “how we think” and the best user onboarding practices

The very first thing we do is create a couple of polls for our trial users. The questions we ask are rather general, such as:

  • What’s your current user onboarding education?
  • Have you installed Userpilot’s javascript snippet?
  • What are their job roles?
  • What do you want to achieve using our tool? (And hence, what product experiments they need)
  • And so on

This helps us to get to know our users better and personalize the second part of our webinar. 

After we finish the introduction, we go through the standard and crisp presentation of the most important Userpilot features.

When it comes to the second part, the majority of products could be accompanied by an entire walkthrough across their product, but we don’t do that.


Because it’s boring. Instead, we tell people the best practices for implementing Userpilot and educate them about user onboarding and product-led growth in general. We show them strategies that work, such as:

  • Don’t create product tours.
  • Don’t create too many steps.
  • Get the user to the “aha!” moment ASAP.

Why do this instead of bragging about our product?

Well, we noticed that the more value you offer, the more success your users will have. More success means they will stay longer with you and bring you more money.

It’s as simple as that.

What Do We Do After Our Webinars?

You won’t experience a big success if you don’t have clearly defined follow-up and call-to-action steps.

In Userpilot’s case, the workflow after the webinar has finished is pretty simple:

  • Demio sends an automated email with the replay session of the webinar so that our attendees can go back to it and listen to it again whenever they want.
  • Elise, our customer success manager, sends follow-up emails.

Those follow-up emails are really important, especially for products like Userpilot where the LCV is big.

The next step for us is to get on a call with our attendees so we can make sure they’re having a successful experience with our product.

This call to action helps us to ensure better trial-to-paid conversions.

Here’s how that follow-up email appears:

Hey {{firstName}},

Thanks again for attending the webinar on Minimum Viable Onboarding, I hope you found it informative and took away some ideas that you can implement into your own onboarding experiences. Please let me know if you have any further questions. Here is my calendar, I would love to see what you building and help in any way I can. 

Thanks again, 


The Bottom Line

As you can see, this webinar strategy helps us to convert over 50% of our trial users into premium plans.

To wrap up everything we mentioned:

  • Make sure you know exactly what your activation rate problems are. Knowing this will help you to create better content for your webinars.
  • Find the toolkit that works for you.
  • Go in front of your trial users by using in-app elements and email.
  • Make sure your webinars are engaging. Don’t forget to offer real value.
  • Always have a clear call to action and follow-up steps after each webinar.



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