We do a lot of pricing transformation projects for companies in the $100-200M ARR range (we also do both smaller and larger, but this week isn't about them) and one of the primary reasons many of them come to us can be boiled down to:

"Growth used to be fast. Now it is slow. We want to get back to fast"

So maybe they got from $0 to $20M at a 200% growth rate and from $20 to $100M at a 50% growth rate, and now they are trending at a 30% growth rate year over year. And slowing down.

And sure: it can be harder to add $50M new ARR now as a mature company compared to adding $3M at seed stage, but still: that feeling of speed and execution and excitement that allowed you to ship product fast and onboard customer in truck-loads... it has gone.

There can be many reasons for this of course (competition, change in leadership, AI eating their lunch etc.), but more often than not we see some combination of three very specific - and very preventable issues - issues:
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ISSUE 1: Commercial Debt

The $100M revenue stack you have is built up with large variance between contracts and dealstructures.

You have a 100 enterprise customers with 100 different contracts, 100 different pricing schemes and a 100 different slight configurations and promises on product.

This is what I call 'Commercial Debt' - and it shows up as operational load.

Renewals get harder (because everyone has a different deal).

Upselling and cross selling is harder (because everyone has a different deal).

Changes to pricing is harder (because everyone has a different deal).

So: Product and Sales spend more time doing stuff that just maintains revenue, rather than growing it.
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ISSUES 2: No Real Enterprise Pricing.

Here is how many companies do enterprise level pricing and packaging:

[Your Mid Market Pricing] + [Unlimited mandate to Sales to create deals]

And since the mid market pricing (by definition) isn't geared to do the enterprise deals, your Sales function will have to step in and incur commercial debt by closing the deal they can get.

So a PS here mid-post: often crazy discounting isn't a Sales problem - it's a downstream sales issue created by an upstream lack of good packaging and pricing.
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To effectively price enterprise customers you must have:

1) Packaging with stuff for the enterprise (e.g. commercial SLAs, bespoke billing, premium support etc.)

2) More complex pricing architecture that taps multiple budgets.

3) Clear deal guardrails for Sales.
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ISSUE 3: Failure to do Multi-Product well

As you grow from $10M to $50 to $100M you will usually add products. Some home-grown and some M&A acquired.

At first this is fine: we have A, but can also do B.

At ABCDEFG it just becomes... a lot. Sales people check out. They ignore the catalog and close out their quarter with the usual A+B combo.

Your 10 products might also have 10 different pricing models: users, API calls, storage etc.

This makes upselling and cross selling harder. And NRR drops.

At $100M you need to balance the need between good pricing on the product level with overall complexity and similarity across the portfolio level.

So sometimes it's better to just price all 10 products 'per user' instead of having different 'local' product models. Sometimes not. But taking the step back and thinking it through is not optional.
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Often we see the big results when you unlock these three:

• Simplify the multi-product pricing.
• Making the offering enterprise-appropriate
• Cleaning up commercial debt.

It can take 1-2 years to truly get through this motion - but you will grow faster afterwards.

And you might just feel like a startup again !
​As promised: a point about pricing every Monday.

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PS: and for my american friends - happy Thanksgiving week! It's been an amazing year here at WillingnessToPay and I am - truly - grateful for the support.

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