Trial users are the key to learning why people don’t convert
Note: this post was inspired by Gergely Orosz’s tweet about automated emails at the end of a trial.
Here’s a common scenario: you sign up for an online tool that you’re curious about. You check it out once, spend a few minutes playing around, and then for some reason, you don’t go back. It might be that the tool didn’t meet your expectations, was missing something important, or you simply got busy with life. Now, 3 days before your trial expires, you receive an email that says:
Subject: Your trial is about to expire
Hi there,We hope you’ve been enjoying your trial of our product! There are only 3 days left on your trial. To keep using our tool after your trial ends, choose a subscription…
Your friendly sales team
It’s a pretty generic message. It doesn’t reference anything you actually did, doesn’t give you any helpful context, and simply urges you to pay without any real conversation.
So who’s driving re-engagement?
In most startups, there’s a disconnect between marketing, product and engineering. Instead of marketing defining the flows for re-engagement campaigns, the product team ends up asking engineers to set up automated emails, who then turn around and ask marketing for the copy.
The email above doesn’t work because:
- It’s not personal. It doesn’t mention anything about your specific experience.
- It’s not relevant. It assumes you loved the product when you might not have even used it much.
- There’s no engagement, no question for you to respond to or any invitation for feedback.
- It asks for money without offering anything in return.
- It feels automated, not a genuine message from a team that cares.
Marketing owns the full customer journey
Getting someone to sign up for a free trial is often the most difficult and expensive step in customer acquisition. At that point, marketing enters the phase of customer retention. So should marketing spend time and money converting trial users? Yes. It’s their job to ask questions and understand why people don’t convert or churn later.
For example:
- Why did someone sign up but never really use the product?
- What stopped them from returning after a trial?
- What prevented them from taking the final step and becoming a paying customer?
A good end-of-trial email should:
- Mention what you did or didn’t do. Shows the compay is paying attention.
- Ask a question or give users a reason to respond.
- Consider extending the trial or providing exclusive features.
- Use a warm, human tone instead of sending a robotic, automated email.
- Create a feedback loop and make it easy for users to share their thoughts about what didn’t work for them.
Here’s a better example of an email the company should send:
Subject: Still deciding? Here’s how to get more time to explore…
Hi Matt,
We noticed you signed up a few weeks ago but haven’t been back since. Just so you know, we’re not giving up on you yet!
If you’re still exploring, we’d love to hear your thoughts. Let us know about your first impressions and three things we could improve by visiting our feedback page: [URL]
Your feedback helps us make the product better, and if something wasn’t clear, we’d be happy to help explain how it works.
As a thank you, we’ll automatically extend your trial by 15 days!
This type of message shows genuine interest in your experience, rather than just asking for money. You’re also giving them a bit more time to ask questions and provide feedback. It doesn’t cost much, the signal is strong, and what you learn might be more valuable than the subscription you didn’t get.
Length of the trial
Research shows that free trials shorter than 5 days have lower conversion rates. Trials from 7 to 30 days have better results. This suggests that while longer trials can help, it also depends on the type of product being offered.
For simple tools (like grammar checkers or screen recorders), a week is usually enough. But for more complex tools, like those for creativity or team collaboration, users often need more time to explore.
However, the length of the trial is not the only factor. A shorter trial with the right support often works better than a longer one with no guidance. What really matters is understanding what the user is trying to do, then helping them get there. That means showing them how the product works, offering clear examples, and making sure they see how it solves their problem.
Conclusion
Potential customers haven’t paid yet, but they’ve shown interest. They’re already in your funnel, curious to see what your product can do. How you treat them in those first few interactions can shape whether they convert, lose interest, or quietly walk away.
“You never get a second chance to make a first impression.”
The trial period is critical for making good first impressions. If someone tries the product and never comes back, don’t just send a money request, try to understand their experience. What you learn from a “no” can be more valuable than chasing another “yes”.
