How to reactivate lost trials

What Canva teaches us about turning churned users into revenue

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I’ve paid for Canva three separate times in the past year.

It’s a cycle of churn → reactivation → churn for me.

I can’t quite justify it long-term (I basically live in Figma), but when I need a one-off feature, I’m back.

And I’m not the only one.

Reactivation campaigns can recover anywhere from 5% to 40% of churned users (even 50% in the case of one gym…) - and up to 38% of lifetime value can come after a user returns.

From a product perspective, there are two key moments in this cycle:

1. The off-boarding flow (which I covered last September - in short, leave the door open)
2. The win-back moment (which we’ll focus on today)

What’s interesting isn’t just that I reactivated - but how.

It happened over two sessions, and across two very different needs.

Let’s break down what happened, what Canva got right and how you can apply this to any product:

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🎯 Session 1: When intent is high, price still matters

I was planning a 30th birthday party. I opened Canva to make the invite. The free templates were… fine.

But the premium ones? Stunnin’. Absolutely gorgeous.

Especially this one:

Everything about this paywall was ✨ contextual ✨ — not generic:

• “⭐ Upgrade to use this template” as the microcopy
• “Unlock our best templates” as the header
• The exact template I wanted featured in the image

But when I clicked upgrade, the first number I saw was £270 — yikes. No trial (which is understanable, given I already had a trial in my first subscription).

Even £27 for a monthly plan felt steep for a single invite.

This was meant to be a ten-minute job, not a template treasure hunt.

So I closed the tab.

Task: incomplete.

📌 Key takeaway: the first number someone sees matters. There’s a fine line between not shocking people with an annual price while also being transparent about how much things cost.

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👑 Session 2: Trials work best when urgency is real

A week later, Canva caught me at the right moment. A moment of even greater urgency.

I was exporting a LinkedIn carousel when I stumbled across some little crown icons on the download settings 👑 👑 👑

Turns out, higher-quality downloads are a Pro feature.

I really needed better download quality in that moment, so I dragged the file size slider. And, lo and behold, I hit another contextual paywall:

But this time, instead of pricing, I was offered a second free trial.

Funnily enough, I’d been shown a trial pop-up a few weeks back and dismissed it because I didn't need it at the time.

This time, however, I took it. But because I was in a hurry 🏃‍♀️🏃‍♀️🏃‍♀️

I needed to get this post out, and I had zero time for friction.

📌 Key takeaway: Reactivation works best when it solves a problem in the moment. Canva likely triggered this trial based on my usage: either time since churn, or it identified that I'd exited of the paywall without paying in my last session.

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🎉 After reactivation: Light-touch onboarding, heavy payoff

After accepting the trial, I got the classic Canva confetti.

Before the confetti had finished falling, I also got a prompt to set up my team.

In the moment, I really needed to finish this piece of content, so I tapped ‘I’ll set up later.’

I don’t know if this onboarding is the same as for new users — or tailored for returners. But it reminded me of what Duolingo does so well: re-onboarding returning users to help them rediscover the magic moment.

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So, what can we learn?

If you’re building a paid product - freemium or not - here are nine things to think about:

1. Don’t treat churned users like they’re gone forever: you don’t just have one shot to get people back, sometimes the third time is a charm. Design systems to support that reality.
2. Make your paywalls contextual: tightly link your paywall copy and imagery to where the user just was and what they want the most.
3. Think of trials not as a one-off but as a lever: just because the second offer of a free trial doesn’t work, that doesn’t mean the third won’t.
4. Play with time-based versus trigger-based offers: the previous reactivation trial I got from Canva a few weeks back felt random (just a pop-up out of nowhere), the next one felt targeted. Play with both types of triggers (time-based and behaviour-based).
5. Help returners find the “aha” moment quickly: what’s the reactivation experience? What moment do people need to revisit in order to stay? Don't just leave them hanging.
6. Let users build investment before the upsell: In both sessions, Canva lets me start the task before showing me the paywall. Creating sunk cost 🧠 - even just a few minutes - increases willingness to convert.

Any more for any more?

Thank you SO much for reading (all the way to the bottom, wow look at you go).

See you next week,

Rosie 🕺
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🚴🏼 I should be in the Pyrenees by now!

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