A bundle takes several things and returns one number.
That number is the only signal you ever get back. It tells you the customer was willing to pay it. It tells you nothing at all about which part of what you sold made them willing.
Most companies never notice the gap, because as long as it stays bundled the question never has to be answered.
The guess, and why it goes the same way every time
Ask a company which half of its offering the customer is really buying and you'll get an answer. It's usually confident and it's usually the part that was hardest to build.
That's not vanity, it's arithmetic. The expensive half absorbed the engineering, the roadmap and most of the meetings, so it's the half the company thinks about. Cost of production is what's visible from the inside.
The customer is running a completely different calculation. They're paying to have something taken off their plate, and what they value is whatever removes the most work, risk or judgement from their week. The two halves are rarely the same half. There's no reason they would be.
So the company's belief about what it sells and the customer's reason for buying can sit a long way apart for years, and the revenue number won't tell either of them.
You find out at the seam
The truth arrives at a discontinuity. A repackaging. A tier split. Retiring a service and keeping the software.
I watched a company do exactly that: it withdrew a managed service and left every customer with full access to the platform underneath. From the inside it read as a plan change, because the thing they'd invested most in was still there.
The customers didn't read it that way. They said, in writing and at length, that the service was what they had been buying. The platform they could take or leave. The company had spent years improving the half that wasn't the purchase.
That's a real answer to a genuinely important question. It just arrives in the worst possible form, all at once, as cancellations, from people who are already gone by the time you read it.
The instrument you already have
Strategic unbundling is usually argued on revenue, and the revenue case is real: hold an item back, attach it to the milestone that earns it, and it prices higher there than it ever did inside the bundle.
But there's a second thing it does that nobody claims, and it might be worth more.
An item you hold back and sell separately produces a price. That price is a measurement. You now know what that component is worth on its own, to real buyers, in the specific moment when they need it. Do it across the things you currently give away inside the first deal and you have an actual map of which parts of your offering carry the willingness to pay, built from purchases rather than from opinions.
Which means the bundle isn't just leaving money on the table. It's leaving the information on the table, and the information is what tells you where to put the next two years of engineering.
What to do with that
You don't need to unbundle everything, and plenty of it has to stay in. Market parity is real, and anything the customer needs in the gap between signing and first value belongs in the first deal regardless of what it would fetch alone.
The candidates are the things you throw in without thinking. The extra seats. The onboarding you stopped charging for. The module everyone gets. Each of those is a thing you have decided is worth zero, and you decided it without ever testing it.
Take one. Attach it to a milestone. Put a number on it. Watch whether people pay.
Now you know something about your own business that you could not have learned any other way, and you learned it from customers who are still here.
Lincoln Murphy formally named and popularized Customer Success starting in 2010 and has spent 15 years connecting it to expansion revenue and commercial outcomes. Read The Premise.