I’ve been through enough B2B SaaS pricing and packaging changes to become skeptical whenever pricing is framed primarily as a math problem.
The number obviously matters. You need to understand willingness to pay, competitive benchmarks, unit economics, discounting, and how a change will affect both new business and the installed base. But in my experience, those aren’t usually the hardest questions.
The hard part is getting the company to agree on what you’re actually charging for.
Pricing forces a bunch of product strategy questions into the open that companies can otherwise avoid. What is the thing customers actually value? Which capabilities naturally belong together? Where should customers enter the product, and what should cause them to expand? Which differences between packages are meaningful to a buyer versus distinctions that only make sense to us internally?
It also forces you to confront complexity.
I’ve seen pricing models that were intellectually elegant and operationally terrible. The spreadsheet worked beautifully, but Sales struggled to explain the packages, customers couldn’t predict what they would pay, or every deal required an exception. I’ve also seen teams spend an enormous amount of time debating whether something should cost $25,000 or $30,000 while ignoring the much bigger problem that a customer couldn’t clearly explain why they would buy one package instead of another.
One test I’ve come to appreciate is surprisingly simple: Can a salesperson who wasn’t involved in designing the new model explain it to a customer in a few minutes without pulling up a complicated spreadsheet?
If the answer is no, the pricing probably isn’t finished.
The best pricing work I’ve been involved with has therefore looked a lot like product strategy. Start with the customer problems you’re solving and understand where value meaningfully increases. Build packages around those value boundaries. Choose a metric that allows revenue to grow as the value the customer receives grows. Then pressure-test the model against the realities of selling, renewing, expanding, and migrating actual customers.
This last part matters more than it gets credit for. A new pricing model can look great for new logos and create enormous friction when you try to move an existing customer base onto it. The migration strategy—what changes, how much it changes, what customers receive in return, and how you handle exceptions—is part of the pricing strategy, not an implementation detail.
That’s why I’ve come to think of pricing as one of the most powerful strategic tools a product company has. It forces you to make explicit choices about your product, your customers, and how you intend to grow.
The actual price is only one of those choices.