If Your Free Trial Was Some Guy on Your Sales Team, I’d Fire Him Today

The free trial – a powerful ally or the single biggest headache in your sales process.

Love ’em or hate ’em, they are important to subscription-based businesses. Giving people a chance to use the premium content and features on your site will connect the dots for them in a way that a sales page could never do.

But there’s a big problem. Your free trial is a lazy bum.

Let’s look at this. For most subscription products, this is the flow that the free trial takes when someone signs up:

Typical trial flow

Typical trial flow

Sounds familiar, right? The customer is given a certain amount of time to experience life behind the paywall without putting their money at risk, and then when the time runs out, they make the call on whether your product is worth paying for or not.

There are two big problems with this approach.

First, the best window of opportunity to turn someone into a customer is when they are most excited about your product, and that is rarely at the moment when the clock expires on their trial.

This would be like if a car salesman at a dealership waited at his desk until after you looked around the lot, sat in the car, breathed in the heavenly smell of leather, took it for a test drive while thinking to yourself “damn I look good in this thing”, and walked back to your car to go home before running after you to see if you wanted to buy.

Obviously he would be a horrible car salesman, because at that point you’ve already moved on from the things that had you really excited about the car. Maybe you loved the car, but you’ve talked yourself out of buying right now – it’s one of the first dealerships you’ve visited and who knows, you may find a better deal or a car you like more somewhere else.

Here’s the thing: most people will figure out very early on in the trial if your product is a good fit for them or not. So why be content on waiting until the full 7, 14 or 30 days are up before you try to get them to act on it?

I’ve got a better idea – but more on that in just a minute.

The second problem in the typical trial flow is that because so much of the conversion effort happens at the point that the trial ends, the conversation relies heavily on the incentive of not losing access (rather negative), instead of being able to frame the sale around the things that hold the most value for them.

You’re also putting the burden of proof once again on your shoulders as you have to find ways to remind them why your product is a good fit for them rather than having the upgrade discussion when they are most convinced. It’s like the car salesman having to remind me several days later how great that feeling was when I was at the wheel. It’s too late. That pitch has lost its power.

If your product resonates strongly with the people trying it out, then losing that access may be enough to get them on board. But it shouldn’t be what dominates the conversation.

So let’s look at how you can shift the strategy for your free trial and address these two problems with your sales process.

First, figure out what your “Wow!” moments are

Free trials become most effective when you get people experiencing the “Wow!” moments of your product.

“Wow! is the moment in a free trial where your buyer suddenly sees the benefit they get from using your product, and says to themselves “Wow! This is great!”. It’s also the moment where you have converted them into a fan who is likely to buy.” – David Skok

These “Wow!” moments are your best opportunities to win a over a new customer, but because you’re banking on the conversion once the trial ends, you risk missing that window entirely. This is what an ideal free trial strategy would look like:

Optimized trial flow

Optimized trial flow

A great way to pin down what the “Wow!” moments are for your own site are to look closely at what the unique strengths of your product are that solve your customer’s problems and that set you apart from their other options?

  • Do you have really high-quality production value in your videos?
  • Is it the depth of your content library?
  • Is it really easy to setup and use?
  • Do you have a unique expertise in this industry that your students would highly benefit from?
  • Are you able to explain complex problems/tasks to people in a way that’s easy to understand and follow through on?

Let’s look at Treehouse (an online training platform for aspiring developers) as an example. During the trial, the parts that stood out for me as the biggest strengths of their product was the learning environment (workspaces that I could actually practice on, progress trackers, gamification) and their ability to explain advanced concepts in a simple way that I can wrap my head around.

Treehouse's "Wow!" moments

Treehouse’s “Wow!” moments

So if they were picking out what the “Wow!” moments are, their list might look something like this:

  • Watching a video and grasping a basic concept
  • Earning a beginner badge
  • Coding in the workspace
  • Completing a course

Their best chance at getting me to become a customer is to get me experiencing the things on that list (and quickly). At the moment that I do (when I finally no longer feel like learning PHP is hopeless), they reach out and make a customer out of me.

It’s important to remember that what you think those “Wow!” moments are may actually not resonate that strongly with your customers. Personally reach out to the people who are trying out your product and find out what caught their attention. When did they realize that there was really something to this.

Tracking when those Wow! moments happen

I expect you might be thinking to yourself, “yeah, this is a great idea, but I’m not standing over their shoulders watching their screens. How do I know when people are hitting those “Wow!” moments so that a message is sent at the right time?”

Unfortunately, there’s no turn-key solution to do exactly that (not quite yet, anyway ?). It’s going to require some development time and help from a third party app to get a system in place that tracks when those events happen and triggers the messages to go out just to people in the free trial.

The best combination of tools we’ve used to set this automation up is Intercom and Segment. If you’re somewhat comfortable around javascript, then here is some documentation on integrating the two for this purpose.

If you don’t have the know-how or the time to set up the tracking and automation yourself, get in touch with us here and we can walk through the process of us building that for you.

How to ship an improvement to your free trial this week

For something you can put in place now, make an educated guess on how long it takes the average user to hit your most important Wow! moments during the free trial. Add one or two messages to your free trial sequence that are scheduled around that timeline.

Don’t make them too pushy. Remember, you already have an agreement with them that they get ‘X’ amount of days to try your product out. Making it feel like you’re nudging them forward will turn them off very quickly.

Instead, focus on the value they would get by upgrading if they already felt confident this was a good fit for them. Let’s expand a bit more on what that conversation should look like.

Improve the sales conversation

By personalizing the calls-to-action in this way, it allows you to address the other big problem with free trials – the fact that the main trigger for people to buy is so that access won’t be taken away from them.

When you are able to ask for the sale at the moments they are most excited about your product, you can reframe the call-to-action to focus more on the positive incentives and the benefits of upgrading now.

“Congrats on completing your first course! Now that you’ve had a chance to go through the material and explore the library, are you ready to dive in?

You still have time left on your free trial, but if you’re ready to start the path towards a better career, you can go ahead and upgrade now and {insert benefits here}.

Those benefits to upgrading could include:
Unlocking full access to features and benefits that weren’t included in the trial
A discount on the first month/year to reward their bold decisiveness
A free bonus gift (ebook, t-shirt, discount with another site/product that compliments yours)

Remember, it doesn’t always take 7, 14 or 30 days for people to come to the conclusion that your product is a great fit for them, so prompting the upgrade before their trial expires is not such a crazy idea (especially when the benefits of them doing so are obvious).

[Main takeaway]: only prompting the upgrade when the trial expires is hurting your sales. Find out when people are most excited about your product and start the conversation there.

As subscription-based products continue to evolve and take over the world, we need to be rethinking our approach to key components like free trials.

The next wave of marketing is all about creating more personalized and relevant conversations with the people who are buying. This is one step in the right direction.