How to Upsell Better from Trials

Whenever a service takes a payment card before a trial, I immediately have a dread of “oh, I bet I forget to cancel this in time”.

To be clear, companies ask for a card in advance, because it removes the need for the user to make a decision (if they want to stick around).

The inverse requires the user to actually bother logging in and entering a payment method—this will create churn.

One UX technique that companies use to calm some of this pre-trial anxiety is to promise that they’ll remind you a few days before your trial ends.

The easy implementation would be a simple email automation, like Canva above.

But you can do better.

Imagine that you’re booking a flight. Which of these two scenarios would you feel more comfortable in:

i.e., you’re more likely to believe in the outcome. Surely the company is less likely to ignore a direct request, rather than a broad company policy, right?

Now look at Rise:

What they’ve done here is smart: they’ve added a toggle to be reminded.

What I imagine the outcome of this small component is:

Not many people who signed up to a service 3 weeks ago, will remember that they’re expecting an email reminder before their trial ends.

So, a quick win: remind the user that this safeguard exists.

Here are two examples, from Duolingo and Nibble:

Something to consider about #1, is that not every product is optimised by taking payment methods before a trial.

To a certain extent, the entire model behind Google Meets is the opposite.

They’ll let you create a meeting with almost no friction, and then when your about to hit your usage cap, you’ll be able to start a trial from within the call.

Think about it like this:

• Google gives you the product for free, with low friction.
• They’ll catch you at a good moment to start a trial in a few clicks.

Or, take Asana, who don’t even require a payment method.

They’ll let you try a premium feature for 30 days, in a single click.

You don’t need to enter a card, they’re not confusing you with a hundred other premium perks—they’re focused on getting you to experience the value.

Before your 30-day trial ends, they’ll start leveraging 🚦 Loss Aversion, and prompt you to enter a payment method before you lose access.

Otherwise they’ll let it expire, and just re-subscribe whenever they next want to use it. There’s little incentive to take action now.

If you can, experiment with just getting the person to use the product, with as little friction as possible—not even mentioning a trial.

For example, Flighty (the flight tracking app) know that the value of tracking a random flight is very low.

But it does allow you to see, and use, all of the features—there’s a button to experience Flighty Pro, at any time.

It’d take some experimenting to implement something like this effectively, but here are a few (fake) ideas:

• When offering social proof, the more specific, the better (Medium).
  • If you run an animation agency, a quote from the “head of animation at Disney” is likely more effective than the same quote from the more generic “Disney”.
  • Likewise, just showing a bunch of company logos is relatively ineffective.
• If you can’t name real people in your social proof, use more generalised statistics, but frame them to be relevant to the user (Babbel).
  • “65% of our users are in the UK like you”
  • “1,035 students are currently learning English too”
• If you have a large existing user base, consider showing realtime numbers, such as “number of new customers today” (HelloFresh).