How to Make “Free” Hurt So Good Users Beg to Pay

Moon Yiu
5 min readJan 9, 2024

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Free trials are a SaaS staple. They get users hooked, let them sample your amazingness, and (ideally) convert them into loyal, paying customers. But what happens when free trial conversions lag? It’s time to get a little… strategic. Let’s talk about loss aversion, a psychological superpower you can wield to turn the tide from trial ghosts to paying champions.

Imagine this: you stumble upon a clothing store advertising a “closing down sale — everything 90% off!” You sprint in, wallet flapping, only to find… the same sale a year later. Talk about anticlimactic, right? Yet, this bait-and-switch thrives because it exploits a fundamental human quirk: loss aversion. We dread loss more than we savor gain. And SaaS founders can leverage this to their advantage.

Think of your free trial as a taste of heaven, with a ticking clock as the fiery gates to hell. “2 days left till free lunch evaporates!”, YouTube whispers. Ecommerce sites scream, “Flash sale ends in 7 hours!” These aren’t just marketing gimmicks; they’re masterclasses in triggering loss aversion. The impending loss of that sweet free service, those valuable features, fuels a frantic need to secure them before they vanish into the ether.

But loss aversion isn’t just about urgency. It’s also about FOMO (fear of missing out). Remember those gym memberships with hefty cancellation fees? They prey on the fear of losing access to all that discounted protein shakes, the nice sauna/steam room, the smug satisfaction of being a gym-goer (even if you never touch a treadmill). It’s a gamble, sure, but the potential loss of those perceived benefits can be enough to tip users towards subscription salvation.

The Art of Framing Loss: Making “Free” Feel Fleeting

Imagine, as a writer, you’re offered a free trial of a fancy AI writing assistant. You craft, it edits, the magic is undeniable. But the clock ticks, and a message pops up: “72 hours until your creativity becomes locked away.” Suddenly, the thought of returning to blank pages and clunky sentences sends shivers down your spine. That’s loss aversion in action, folks.

Instead of just highlighting the features you gain with a paid plan, emphasize the pain of losing what you’ve tasted. No more instant grammar checks? No more AI-powered brainstorming? Paint a picture of a writerly dystopia, and watch conversions rise.

Beyond Urgency: The FOMO Factor and the Power of Perceived Value

But loss aversion isn’t just about the ticking clock. It’s also about the fear of missing out, that nagging suspicion you’re leaving something valuable behind. Think of those fancy analytics your free trial offered — those actionable insights, those competitor comparisons, the sweet, sweet feeling of data-driven power. Losing that can feel like walking into a business meeting blindfolded.

Now, imagine a marketing SaaS. Their free trial gives you a taste of targeted ad campaigns, conversion tracking, and audience insights. Then, boom! A gentle reminder — “Upgrade before the insights disappear! Don’t be left guessing in the marketing dark.” Suddenly, subscribing isn’t just about features; it’s about avoiding strategic oblivion.

The Ethics of Enticement: Wielding Loss Aversion Wisely

Remember, trust is your ultimate currency. Don’t resort to cheap tricks like fake scarcity or blatantly manipulative tactics. Focus on the genuine value users lose by staying free. Show them how much better their lives (or businesses) could be with your paid features. Let the power of loss aversion do its work naturally, without resorting to emotional manipulation.

So, how can you harness this potent force for your SaaS? Here are some pro tips:

  • Highlight the potential loss during free trials. Don’t just tout what they gain when they convert; remind them of what they’ll lose when the trial ends. No more unlimited storage? No access to advanced analytics? Make it sting!
  • Frame cancellations as losses, not gains. Instead of focusing on getting their money back, emphasize the lost benefits. No more personalized recommendations? No priority customer support? Paint a picture of a bleak, featureless wasteland beyond the paywall.
  • Employ limited-time offers strategically. Flash sales, countdown timers, last-chance deals — they’re not just for ecommerce anymore. Use them to create a sense of urgency and trigger that fear of missing out on limited-time perks.
  • Be ethical, not manipulative. Remember, trust is key. Don’t resort to fake scarcity or fear-mongering. Focus on highlighting the genuine value users lose by remaining free, and let the power of loss aversion do the rest.

Here are the real-world examples of successful Saas products:

  • Grammarly: Their free plan gives you basic checks, then gently nudges you towards pro features with messages like, “Unlock advanced suggestions to eliminate hidden errors and write with clarity.”
  • Canva: Their free plan lets you create basic designs, but upgrading removes watermarks, unlocks premium templates, and grants access to a massive library of stock photos. The pain of losing those visual goodies can be quite persuasive!
  • Slack: Their free plan gets you started, but upgrading for unlimited messages, searchable history, and guest access ensures you never miss a beat. The biggest fear would be when you lose all your chat history and data!

By understanding and leveraging this powerful psychological principle, you can turn “free” into a potent motivator, nudging users from trial dabblers to passionate, paying advocates. So, stop hoping and start strategizing. Let loss aversion be your secret weapon, and watch your conversion rates soar. Just remember, wield this power wisely, with transparency and a focus on real value. Because in the end, happy, paying customers are the ultimate win, and loss aversion is just the tool to get you there.

What are your thoughts? We’d love to hear more! Feel free to reach out to me via LinkedIn or Twitter for shorter tips on how to craft the next viral product.

Moon is Founder & CEO of DigitSense, a digital product studio that design, develop, and market digital products like a tech startup on its own, where we blend cutting-edge tech with user-centric magic to transform your vision into reality.

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Moon Yiu

Turbocharge your software product from concept to unicorn 🦄 | Tech entrepreneur | Founder of DigitSense | I craft products with user obsession 🪄