20 Signs Your Pricing Is Broken

I frequently get asked: “how do we know our pricing needs a revisit?”

Spoiler: it’s not just when your contract says it’s time to inflation index.

Pricing isn’t set-and-forget. It’s a muscle you need to train and maintain. And while some signals are obvious, others are more subtle.

Here are 20 signs you’re leaving money on the table.

1. No pushback? You’re too cheap.
   If prospects never push back on your pricing, you’re probably too cheap.

2. Your churn is “too good”
   Yes, there is such a thing as healthy churn. If no one’s leaving, you’re not pushing enough.

3. You haven’t touched pricing in 2+ yrs
   Revenue = deals x price. If you’re only optimising deal volume, you’re neglecting 50% of the revenue formula.

4. Heavy users say you’re cheap
   Ignore what most users are saying about pricing and listen more to your power users. They can point you in the right direction.

5. No one is upgrading
   Acquiring customers is just the beginning. You need to have a pricing strategy to grow them.

6. Power users aren’t power payers
   If your top 10% aren’t paying 10x the average, you’ve got a value capture problem.

7. You’re discounting like it’s Black Friday
   If discounting is the rule rather than the exception, your list price is nothing but an illusion.

8. Your AEs struggle to explain it
   If your reps can’t explain your pricing clearly, they’re in no position to win.

9. Your ICP changed
   Your legacy customers shouldn’t dictate your pricing strategy. Your ICP should.

10. You solve new problems now
    New use case = new monetisation strategy.

11. You’re solving the same problems, but better
    New functionality leading to more value for your customers? Update your pricing accordingly.

12. You raised a boatload of cash
    If you’re in venture-mode, subsidising to capture market share might make sense.

13. No one owns pricing
    When no one in your organisation owns pricing, it’s likely been neglected for a while.

14. Competitive pressures
    If your competition is coming after your market share, pricing and packaging can provide an edge. Focus on making it easy to start and expand customers as your lock-in strengthens.

15. Increasing churn
    While rare, high churn can be caused by high prices. However, please note that many people rather blame price than share tough feedback with you.

16. Low adoption
    Are you pure usage-based or pure outcome-based? You might struggle with low adoption due to lack of skin-in-the-game. Platform or implementation fees can help.

17. Functional pricing tiers
    Even in 2025, many software companies are focussed more on functionality than value. Yet customers allocate budgets to solving problems rather than features. Introduce tiers based on jobs-to-be-done.

18. Improved usage analytics
    When you’re first starting to analyse your usage data, you might identify user patterns. Focus on features used heavily by small groups and consider turning these into add-ons.

19. You’re simply the best
    Solving a particular problem 10x better than any other alternative? Consider adopting premium pricing. See Superhuman for flawless execution of premium software pricing.

20. Tailor-made trouble
    You’re always offering bespoke deals to any sizeable customer. Over time this legacy becomes unsustainable.

There you have it: 20 signals your pricing might be broken.

Successful companies understand pricing isn’t set-and-forget.

Pricing is a reliable growth lever you need to train and maintain.

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