B2B SaaS companies tend to grow quickly and then stall somewhere between $10M and $100M ARR, for a reason that never shows up cleanly on a dashboard. What's happened is that they've accumulated something we call commercial debt without anyone raising a flag about it. They're now spending so much energy maintaining a tangle of bespoke customer agreements that they can't reprice, can't expand efficiently, and can't get out of their own way.

Complexity and drag arises from supporting a hodgepodge of different commercial agreements without a clear system.
‍
- Ulrik Lehrskov-Schmidt, author of The Pricing Roadmap

What is commercial debt?

Commercial debt.
‍
The operational load created by variance across your customer agreements - different contracts, prices, packaging, and terms accumulating from one exception at a time until the variance itself becomes a heavy, invisible tax on everything the company does.

A note on the name: we didn't invent it. We borrowed it from a Visma CFO who used the phrase in a keynote some years ago, and it captured something we'd been describing without a word for it since the mid-2010s.

The variance itself builds from short-term decisions that each look completely reasonable at the time. A deal is close, but the customer won't take the standard contract.

They want a feature from the enterprise tier, monthly billing instead of annual, a fixed price instead of per-user, a different cancellation term. They're important, and they'll sign if you just give them this one thing - so the exception goes in. Each bespoke deal looks almost identical to the others, just a slight variation from the baseline.

Stack five hundred of them, and the variations become the dominant feature of your customer base. Nobody designed the resulting mess; it accreted, one sensible "yes" at a time. Commercial debt is never a decision - it's the sum of a thousand small ones.

Where commercial debt shows up

Once you know what to look for, commercial debt shows up in three specific places. Any book of business past a certain size has at least a bit of it. You'll probably recognize at least one of these from your own:

Renewals get hard. When every contract is different, each renewal starts with re-learning the account - "What was that deal again?" What did we promise them, at what price, on what terms? In practice, finance ends up keeping a spreadsheet of bespoke renewal terms - this customer's custom price-increase cap, that one's ninety-day notice period, another's special uplift schedule - and works it by hand, one account at a time. Multiplied across a portfolio of one-offs, you can see how renewals become a real problem.

Expansion goes manual. Upsell and cross-sell stop being repeatable motions, because what a customer can be sold next depends on the particular bundle and terms they happen to be on. Every expansion conversation becomes bespoke, and the CS team spends more time reconstructing the account than selling into it.

Pricing changes become nearly impossible. This is the most expensive symptom of the three. When you finally want to raise prices, you can't just send an email. You have to reopen hundreds of individual contracts, each negotiated differently, many requiring the customer's explicit consent to change.

If all these three symptoms feel familiar, you already know you're dealing with commercial debt.

The link with technical debt

There's another cost worth naming here - one most companies never connect to commercial debt at all, because it lands on the engineering team's plate instead of the sales team's.

Every time sales closes a deal with a non-standard term - a bespoke feature, a custom configuration, monthly billing for one account - someone has to build and maintain that exception in the codebase, the billing system, or both.

Which means commercial debt doesn't just accumulate on the commercial side. It accumulates on the technical side too, and in our experience the causation almost always runs in that direction: commercial debt drives technical debt, not the other way round. The trap is that engineering teams watch only the technical side, which is why the commercial side runs unwatched for years.

That's why the useful test to run against any concession isn't "does this win the deal?" but "does this build commercial debt, and does this build tech debt?"

If you're making an exception to close one customer, that customer had better be worth it. Otherwise, you're adding top line without any bottom line to show for it. We call that fluff value, and it's what fills the pipeline of a company that looks healthy on the surface but can't scale.

Why commercial debt stalls growth

The commercial debt that drives all of that has a predictable onset. Most companies run on a hustle-first mentality in the early years, and that's the right call - closing deals however you have to is how you prove the business exists in the first place. The trouble starts when that mentality doesn't retire on schedule. Around $10M ARR, a company's accounts are usually already sitting on different formats - legacy pricing, a since-bought-out channel partner's terms, two product versions' worth of contracts - and the variance starts to bite. From that point onwards, more and more of the organization's energy goes into handling existing business rather than winning new business, and the growth curve flattens out.

The cost of getting to that point can be enormous.

One case we worked diligence on: an enterprise software company with about 600 customers that was under-priced by an estimated 85% - a clean catch-up to market that everyone in the boardroom agreed on.

But, because those 600 customers sat on 600 different contracts spread across various hard drives, capturing that value would have meant putting the entire sales force on renegotiation for eighteen months instead of selling. The company sold itself instead of raising prices, because the operational cost of the catch-up was higher than the payoff.

Another we've watched play out: a US HR-tech company that rocketed to $85M ARR and then spent five years stuck below $100M, running on razor-thin margins despite a blue-chip enterprise portfolio - because every account was a hand-held, manually signed contract that procurement had ground down.

Impressive top line, almost no bottom line, and no way to reprice the book without opening every deal from scratch.

This is also why repricing gets blocked upstream so often. When teams look at why they can't raise prices even though every signal says they should, commercial debt is usually the real obstacle - not customer reaction (see also: SaaS Price Increases & Repricing at willingnesstopay.com/saas-price-increase).

‍

How to avoid it: one framework and a dynamic contract

So, if commercial debt is the problem, the cure is structural discipline - one contract framework, one pricing framework, one discount framework, and a refusal to deviate outside controlled limits.

Hold that line long enough, and every customer ends up sitting inside a single system, which means you can change prices or product across the bulk of the base by sending an email - Netflix-style - instead of renegotiating a book.

In B2B enterprise this doesn't mean one identical contract for every customer. It means one framework with pre-designed variance - a set of pre-approved "deviations" customers can choose from - so the flexibility lives inside the framework rather than outside it.

The very largest deals (roughly €1M and up) will always be individually negotiated, and that's fine; you can command a premium for the bespoke work. You can also charge an explicit fee for accommodating custom terms more broadly, since large enterprises already know that flexibility costs something, and pricing it removes the awkwardness of negotiating it deal by deal. None of this creates commercial debt, because the variance was designed into the system in advance rather than improvised deal by deal.

The contract itself is where the discipline starts. We call the shape it needs to take a dynamic contract framework, and it has three non-negotiable features.

The dynamic contract framework: three non-negotiable features

A useful test to run on your existing contracts is a simple one - can you raise prices without triggering a formal renegotiation? If the answer is yes, you're already ahead of more than 80% of B2B SaaS contracts we come across in engagements.

The quid pro quo is that you don't lock the customer in on their side either.

We recommend asymmetrical cancellation: the customer can leave on a month or a few months' notice, while you give twelve to twenty-four months' notice before ending the relationship.

Predictability comes through time-limited discounts and grace periods rather than perpetual fixed terms (Salesforce famously stepped discounts from 90% in year one down to 0% by year ten).

Procurement will resist a dynamic framework at first - the honest answer is that a SaaS product is a living thing that keeps evolving, so what they sign for today simply won't be what you deliver in a few years. That's the whole point of SaaS.

Concessions without debt

So this framework might hold up in theory. But in practice, it has to survive an enterprise sales process - which means you can't run it with zero flexibility. The trick is to give ground in ways that don't leave permanent variance behind.

We rank the concession types by how much commercial debt each one creates, from least to most.

The concession hierarchy (least to most debt)

The rule that follows from the hierarchy is simple in principle and hard in execution - keep every concession time-limited or one-off, and never permanent.
A permanent price discount, a "free forever" add-on, or a bespoke payment profile bakes variance into the base indefinitely.
Give sales management a catalogue of pre-approved guarantees, planned concessions, and bonuses - plus a tight, structured discount mandate - so reps close inside the framework rather than around it. Two rules keep the mandate itself from quietly leaking debt: quote any discount longer than a year in nominal value ($), not percentage, since a "10% discount" silently becomes a bigger concession every time you raise the list price, while $1K off is always just $1K off, no matter what the list price becomes.

How to clear existing commercial debt

So far, so good if you're starting from close to a blank sheet. If you're not - and most B2B SaaS companies aren't by the time they take pricing seriously - the debt's already on the book, and clearing it takes a deliberate cleanup.

The vehicle we use is a full pricing or packaging redesign, because a redesign gives you a legitimate reason to migrate every customer onto a new, uniform structure at once.

The pattern is easy to describe and hard to execute: design one new framework, then spend two to three years migrating every customer onto it at their next renewal - presented as an ultimatum, not a negotiation.

When it lands, the same project reprices the book, cuts operational cost, and restores the ability to change prices without renegotiation. In some cases the operational savings alone are enough to unlock growth without touching the price list at all.

Contractbook came to us with an unscalable pricing model, and the redesign into a clean tiered framework accelerated growth enough to support a $30M Series B eighteen months early. (Contractbook case study: willingnesstopay.com/case-studies/saas-packaging-pricing-redesign-for-contract-provider)

Envidan came to us carrying decades of legacy structure from perpetual and on-prem licensing, and the redesign supported a 600%+ price increase with zero churn while standing up a self-sustaining SaaS division inside the company. (Envidan case study)

Same pattern in both cases: one framework, a renewal cycle to migrate, and the cleanup itself as the moment to reset pricing.