Two killer pricing mistakes

Pricing is one of the highest-leverage decisions a startup can make—but too many founders treat it like a detail instead of a core part of product-market fit. While there are many ways pricing can go wrong, two of the most common mistakes fall into the same trap: complexity. Either they force customers to understand a convoluted pricing structure, or they build an overly complex system on the backend that slows down sales, onboarding, and product velocity.

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Super complicated pricing

The first mistake: forcing customers to decode your pricing. Founders often spend too much time trying to make their pricing reflect every little nuance of their product—every feature tier, every integration, every edge case. The result is a matrix that might make sense internally but looks like a puzzle to the outside world.

Think of the enterprise SaaS startup that charges based on a mix of users, data usage, and API calls, all wrapped up in opaque tier names like "Professional" and "Business Plus." No one outside your company will take the time to understand that. If you make potential customers do math or consult a glossary, they’ll bounce. Worse, they might put it into ChatGPT to decode it for them. Where they’ll likely also learn about competitors.