SaaS Free Trial Experiment: Unexpected Lessons

The Trial Subscription Rollercoaster: Lessons from Implementing a 3-Day Free Trial

The Beginning: Automating Our Trial Process

So, on 8th May, I added a 3-day trial to our subscription plans. The users would add their credit card details during checkout, and our payment provider (Paddle) would manage the 3-day trial.

Before doing this, the users would send a support ticket, and I would add them to one of my workspaces so they could try out the platform.

It was an exhausting cycle, and I had to monitor when I had to reach out to them (on trial end).

Then, I thought we could automate this. The payment provider would be able to manage everything, including user statuses, and the users wouldn't need to contact me to do this.

From 8th to 20th May (today), we had 30+ trial users on our platform; the system worked! If I run the numbers, we have a 50% conversion rate from trial to paid.

We were able to get some users who had signed up on our platform more than 10 months ago to start a trial, which felt like a huge win!

Tracking User Behavior: The Good and The Bad

Since this is something new that I was trying out, I wanted to see how these trial users were behaving on our platform. I have set up custom events on Usermaven so that we can check which features are getting used more; the workflows are monitored through Funnels and Journeys. I was checking the other metrics through Paddle's ProfitWell and Retain.

Since we launched the trial plans, almost 40% of the subscriptions were for the annual plans. This was incredibly exciting because annual plans are the holy grail for any SaaS founder! They reduce churn by locking in users longer, improving cash flow with upfront payments, and giving us more runway to improve the product. Plus, annual subscribers are more committed users who provide better feedback. As a bootstrapped founder, seeing those annual plan conversions made my day each time the notification came in! 😁

But then, after the 3-day trials, the annual plans were never activated; I saw the logs, and the subscriptions were canceled before they were billed.

The Plot Thickens: Payment Issues and Clever Users

The other issue I noticed from ProfitWell with the trial users was that their payments failed. Paddle Retain would start sending them emails to retain them, but they would not go through. I reached out to a few, asking them what went wrong, but I never heard back from them. The logs show they were pretty active during the trial period but didn't want to pay for it.

Then came the brilliant ones... 😀

After a subscription expires, users can either resubscribe to a paid plan OR revert to the Free plan. The users would take the 3-day trial, cancel, get their subscription expired, revert to the Free plan, and then start a 3-day trial again 😅 Hahaha, this was the funniest/saddest thing, and I don't think I could have even imagined this scenario in my wildest dreams!

When Trials Go Wild: The Extreme Users

Then came the abusers... 🥲

I am sure these users had blocked everything on their calendar and dedicated their entire existence to PostNitro when their trial started 😅 Every custom event was triggered 3x more than usual in the past 10 days. I noticed this when, in a single day, I saw 82 carousel videos, 224 PDFs, and 97 PNG files downloaded, all from 4-5 different trial account users. For all of this, they were usingthe premium AI models to generate the content for the slides.

Haha, the past 10 days have been the most interesting in my two years of founding PostNitro. Too many things happened too fast and too close together. It was an exhilarating experience, and I learned so much from all this!

Key Lessons Learned

• Always have some measures in place to prevent abuse of your platform, especially if your running cost can get out of hand.
• The trial is an excellent idea, and I contacted the converted users. They like the platform more now that they've understood how it works.
• Set reasonable usage limits during trials - I should have capped daily exports or AI generations to prevent the "download everything" marathon sessions.
• A cooling-off period between trials - requiring at least 30 days before someone can start a new trial would have prevented the trial-cancel-repeat cycle.
• Be more strategic with trial length - 3 days might be too short for some to fully evaluate but long enough for others to extract massive value without converting.
• Track specific feature usage during trials to understand what drives conversions vs. what drives abuse.
• Pre-qualify trial users better - perhaps requiring a 15-minute onboarding call would have weeded out the abusers and increased our conversion rate.

Would I Do It Again?

So, would I bring the trial subscriptions back? 100% yes, but this time, I would do it smarter! I should have known and set up contingencies before launching the trial plans. I built this fantastic playground but forgot to put any fences around it! The emotional rollercoaster was intense - from the elation of seeing those trial signups and the initial 50% conversion rate to the disappointment of watching users game the system. There were moments I facepalmed at my desk, seeing the usage logs, and burst out laughing at how creative some users were in maximizing their "free" experience. Despite the challenges, the trial gave us invaluable data on what users really want from PostNitro - information we couldn't have gathered any other way.

At PostNitro, I've experimented with many things, be it features or pricing, and every time, I've sat down and taken a retrospective. I have always understood what went wrong, where or what went excellent, and how to improve it. One of the best things about PostNitro is that I've reached so many people worldwide; you can be a part of my journey to being a SaaS founder on X (Twitter) as I share my lessons there more often. 🙂

We are offering a 50% discount on the annual plans until 31st May, which will benefit everyone. Checkout or upgrade and the code will be applied automatically.