You used to be able to revisit pricing once every 18 months. Now it could be out of date within 6 months.

I’ve advised more than 100 SaaS and AI founders on their pricing and monetization, including more than a dozen already in 2026. Pricing anxiety is higher than I’ve ever seen it before and nobody seems to be happy with their pricing. Even a giant like Salesforce just announced their fifth AI pricing model (🤯) in fewer than two years.

Each pricing model comes with so much baggage. Flat-fee subscriptions block upsell. Seat-based pricing isn’t future-proof. Hybrid pricing is too difficult to explain. Token pricing is getting commoditized as enterprises shift away from tokenmaxxing.

Up today: 4 questions to ask to see if your pricing model needs to change. Plus, proven tools, Claude skills, and frameworks to improve your pricing strategy.

🔓 Bonus for paid subscribers: Tools to run your own pricing project and a new Claude skill to design a willingness-to-pay survey.

Perhaps the most important reason to change pricing is that your goals have changed.

You’ve moved from prioritizing growth-at-any-cost to profitability. You’ve pivoted from SMB to Enterprise customers. Or you’re shifting gears from new logo acquisition to building an expansion motion.

Show me what you’re optimizing for, I’ll show you the right pricing strategy.

One small problem: most leadership teams I’ve worked with haven’t clarified their objectives (aside from perhaps an ARR target). Each function focuses on different metrics. Pricing gets caught in between.

How to do it: The pricing trade-off exercise

Start by writing down the 3-5 most important business objective decisions that relate to your pricing. My go-to’s are:

Send this exercise to your executive team as a poll. Each leader should fill it out without being biased by what others think — this is what gives you a clean baseline.

Map how everyone voted on the slide above. Then discuss the discrepancies in your next exec meeting. This gives you the North Star for your next pricing decision.

Pricing can look great on paper. But what matters is how prospects perceive it.

My rule of thumb is that you should aim to lose 20% of deals due to pricing.

Why 20%? It filters out prospects who don’t have budget or didn’t see much value in your product — these wouldn’t be great customers anyway. But it’s not so high that pricing is a major barrier to winning deals.

If you barely get any pushback on pricing, that’s a powerful signal on its own. The signal: your prices are probably too low.

If you’re losing 40% or more of your deals due to pricing, that’s a red flag. Something changed in the market and what you’re doing isn’t working.

How to do it: Win-loss pricing analyzer