Want to know what really works in subscription monetization? After leading growth at companies like WWE and Nickelodeon, I’ve found it’s not just about what you charge – it’s about creating value that makes customers happy to pay.

Let me share a story from one client. We were trying to get more people to upgrade to our premium tier, but our normal tactics weren’t working. When we dug into the data (like we learned in the Marine Corps: assess before you act), we found something surprising. People weren’t upgrading because of the extra features we offered. They upgraded when they felt part of something special.

So we changed our approach. Instead of just blocking off features in different tiers, we started giving new users full access to everything for a short time. We showed them exactly what they’d be missing if they didn’t upgrade. This simple change made a big difference – our upgrade rates went up significantly.

But here’s the real secret: good pricing isn’t about tricks or pressure. It’s about matching what you offer to what different customers want. At another client, we found that some users loved exclusive content, while others wanted early access to new features. So we built our pricing tiers around these different groups.

Here’s what works:

Let people try everything during their trial – don’t hold anything back. Eleana Verna calls this the Reverse Free Trial.

Watch how people use your product, then build your pricing around that

Create clear reasons to upgrade based on what customers actually value

Make each tier feel special and worth the money

Want to know if your pricing strategy is working? Here’s my simple test: Are your customers getting more value over time, not less? If not, it’s time to rethink your approach.

Remember: In subscription businesses, the goal isn’t to get the most money from customers today. It’s to create so much value that they’re happy to pay you more over time.

Like we say in the Marine Corps: Mission success isn’t about short-term wins – it’s about long-term victory. The same is true for subscription pricing.

Want to talk about building a monetization strategy that actually works? Let’s connect.

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I help subscription/SaaS businesses with growth strategy and execution so they can grow in a predictable, repeatable way. I have 20+ years of experience leading growth at startups like Curiosity, mid-sized companies like WWE, and large companies like Viacom/Nickelodeon.