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How to Win Back Users who are Abandoning your Trial

Lots of people start trials, then for whatever reason abandon them. With these few tips you can make sure users complete their trial and stay on the path to become a happy customer.

Stephen Nancekivell
Stephen Nancekivell
Senior Software Engineer
February 1, 2023
How to Win Back Users who are Abandoning your Trial

Who hasn’t excitedly signed up for a free trial believing that a new program or service might just change your life – and then forgot all about it? Life happens. Changes in priorities happen. Enticing weekend plans or urgent work deadlines happen. There are a number of potential reasons your users are abandoning your free trials that have absolutely nothing to do with your product. And there are some that also have to do with obstacles in your onboarding process.

So, what can you do about it? You can monitor their onboarding journey and reach out at the right times to get them back on the path to becoming happy, paying customers.

What does that look like? We’ll show you.

How to Catch Users Likely to Abandon your Trial Before it’s Too Late​

With most subscription products, the journey from a free trial to a paying subscriber has significant commonalities. While some eventual subscribers might spend more time using your product than others and some might take advantage of specific features while others don’t, there are usually key indicators in your new user onboarding journey that indicate (based on your past data) that their free trial is setting them up to convert.

You can predict which users are going to convert and who is going to abandon their trial. If you know early, you can do something to get them back on track. If the trial runs out it is too late, you then have to convince them to come back and try again - often without another free trial.

Here are some ways to pinpoint users that are in danger of not converting early:

Activation Metrics​

Activation is the key action that shows a user is getting value out of the product and correlates strongly with them completing a trial. For a music streaming service this would be creating or following a playlist or listening to a song on the 2nd day of the trial.

For a project management software application, that might include things like adding team members to the company account,, starting projects, setting up boards,, or updating their progress on projects.

Essentially, activation metrics are any data points that show a user is setting up their account, actively using your product, or completing important milestones. These are the things that make them more likely to convert at the end of the trial. You might also find some surprising activation metrics if you dig deep into your data.

Once you know what optimizes a user for conversion, you know which of your users are on the right path – and which might need a nudge getting onto that right path.

Time to Complete Each Step​

So, what if a user is completing all the right milestones – but they're doing it about a week or two later than other users? That’s a bad sign. While it could just mean they got a bit busy and didn’t set up their account as quickly as other users, it could also mean that they’re not as engaged with your product and that they won’t have enough time to get a good idea of how it works or complete all the activation milestones before the trial comes to an end. That’s not what you want. You want your users to love your product so much by then and to have completed all the steps that help with conversion that they have a high likelihood of subscribing immediately. No thought or deliberation needed.

If users are lagging behind completing key activation steps, you should have a way to give them a nudge so that they get back on track.

Manual Review​

For many companies, it makes sense to have someone manually look at the new accounts a day or so after users sign-up. Why? Because you would be shocked by what you can find out by doing that.

For example, let’s say you’re a database company and multiple people on the infrastructure team at a very large tech company sign up for free accounts. That’s a good indication that they might be testing out the database to potentially launch a new product or service on. An account manager can flag that account for extra monitoring – and potentially even reach out to those customers personally to offer a more personalized onboarding experience, custom pricing options, or help conceptualizing their project. A personal touch point will also allow you to get more information about what they’re planning to use the database for.

While it’s impossible to provide every new user with such a high touch onboarding process, there are certain users that could make such a big impact on your ARR (Anual Recuring Revenue) that it makes sense to offer a more hands on onboarding process. Even if it doesn’t make sense to reach out directly, an account manager can check weekly to see how certain VIP accounts are moving through the activation process – and reach out to help if there are any road bumps.

Ways to Reach Out​

Once you know what it looks like when your users are off track, you can reach out to them to try to get them back on track. Here are some good ways to do that:

Email Onboarding Drip Campaign​

Ever have someone dump a lot of information on you all at once? It was overwhelming, wasn’t it? You should be sending an email onboarding drip campaign to all your users but you should have a special one for users who seem to have abandoned their trials.

Every few days, you can email them talking about another use case, linking to a different tutorial, or offering help. You can also write these emails to look like they’re personal messages coming from real people at your company offering to help or asking for feedback on their experience.

They should be set up so that if the customer responds to the email by completing an activation milestone, they get another email helping them complete the next activation metric. But if they don’t? You send them an email that asks for feedback or offers a higher touch solution.

Onboarding Tutorials and Tips​

What does your onboarding flow look like? Do you have in-app tips and tutorials that pop up for your new users when they check out different parts of your product? Do you have a setup wizard that keeps track of which activation steps they have yet to complete and messages them with a nudge or tips to complete it when they sign in?

Love him or hate him, Microsoft’s Clippy helped a generation learn how to navigate a whole new word processing experience. What would your Clippy look like or say?

In-app Support​

You likely know what it looks like when your users are confused. They might spend a lot of time on the settings page or looking for something in your UI. If there are certain signals that indicate that they likely need help understanding something, that’s a great time to hit them with a popup from a chatbot or your customer service team offering to help.

Proactive customer service is always more effective. By offering help before they become frustrated with your product, you optimize them for conversion at the end of your trial.

Onboarding Webinars​

Another great way to reach out to users who get lost in your onboarding flow is to invite them to an onboarding webinar. You can either automate this as part of your drip campaign or have someone manually email the new user.

This is a great way to help people who need more hands-on learning opportunities or might have questions they want to ask you directly because they’re stuck on how to use a particular functionality.

Ways to Win Users Back​

Now that you know what to look for and how to contact them, what should you remember about how to win them back?

Remember these four key tips for getting users back on track:

  1. Help them learn: Learning a new software program can be hard, even if your product is designed intuitively. Think about sending them tutorial videos, inviting them to webinars, doing a demo, or linking them to your great docs.
  2. Show your value: Why should they use you? Make sure in your communications with them during your trial to send them things like info about relevant use cases, case studies showing the total value of ownership of your product, and info about how to use cool features that will make their lives easier or better..
  3. Keep them moving through the flow: Some users get stuck on activation milestones once and then they’re fine. Others get stuck repeatedly. Make sure you continue to help users move forward by offering them the help and support they need to do so every time they seem stuck.
  4. Sweeten the deal: If you notice someone isn’t moving through the flow at the same speed as customers that generally convert, you might decide to sweeten the deal to get them interested. Offer them a free seat for a colleague, a limited-time upgrade if they convert, or an extension of their trial period. You can test different ways to sweeten the deal to see which are most effective at converting. The goal is to improve your conversion metrics by better understanding why your customers are hesitating in adopting your product.

The Bottom Line​

The secret to optimizing your free trial conversion rates isn’t just ensuring you get as many people into your free trial funnel as possible and hoping things work out for the best. Users currently in your free trial are at a critical point. You’ve already convinced them to try your product out – now you just need to get them over the hurdles involved in adopting your product.

Ensuring that you have automated and manual ways to detect when users are getting stuck in the funnel and strategies for how to get them back on track is key for improving your conversion metrics and revenue.

At Upollo, we help SaaS companies optimize their revenue by helping them convert more happy paying customers. That might mean helping you pinpoint users who are repeat trialers or account sharers – but it could also mean helping you track your users’ journeys and optimize your messaging to them. We’re here to help you succeed at every stage of your users’ journeys.

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About the Author
Stephen Nancekivell
Stephen Nancekivell
Senior Software Engineer

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