When we sat down to figure out how to price Measure, we started with a simple question: if we ignored how everyone else does it, what would actually make sense for both us and our customers?

The honest answer? Revenue-based pricing would be cleanest for us. We have your revenue data. We grow when you grow. It scales proportionally. From a pure business model perspective, charging a percentage of revenue makes perfect sense.

But somewhere between $500K and $10M ARR, percentage pricing stops working. Not because the model is fundamentally broken, but because the incentives start conflicting with the product's core purpose.

The cost predictability problem

As you scale, software buyers want to know what they're going to pay. Not approximately. Not "it depends on how much revenue you process." They want a number they can put in a budget and defend to a CFO.

Revenue-based pricing makes that impossible. Your Q4 is great? Your billing software bill spikes. You have a down quarter? At least your tools cost less. The variability might be proportional, but it's still variability.

And then there's the psychology problem.

When Stripe charges 2.9% + $0.30 per transaction for payment processing, that makes sense. They're handling payment risk, fraud prevention, compliance, chargebacks. The percentage is tied to the actual risk and operational cost of moving money. You're paying for the pipes your payments run through.

But when your billing software charges a percentage of revenue, what are you actually paying for? Invoice generation. Revenue recognition. Commission calculations. The same functions whether you're processing $100 or $100,000.

Getting a bill that scales with your revenue from a vendor who isn't taking any payment risk just feels wrong. And it is wrong, because the value delivered doesn't scale the same way the bill does.

The pricing model that undermines its own product

At $2M or $3M ARR, percentage pricing still works. A fraction of a percent feels reasonable. But somewhere between $5M and $10M ARR, the math stops making sense.

You close a $500K enterprise deal. Stripe Billing charges you $3,500 in fees (at 0.7%) just to generate the invoice and track the subscription. Same system, same functions, same few minutes of compute time. But because the number is bigger, so is the bill.

So you do what every finance team does: you route the deal outside Stripe Billing to avoid the fees. Maybe you handle it in your CRM. Maybe you build a one-off invoice. Maybe you just track it in a spreadsheet.

And here's the problem: Stripe Billing's entire value proposition is being your billing source of truth. The single system where all your contracts, invoices, and revenue data live. The thing you bought it for.

The pricing model actively incentivizes you to undermine that. Every large deal you route around the system makes Stripe Billing less valuable. Your reporting fragments. Your revenue recognition goes back to spreadsheets. Your commissions need manual calculation. The single source of truth becomes three partial sources that need reconciliation.

This isn't a side effect. It's the inevitable result of pricing that conflicts with the product's purpose. The bigger and more successful you get, the more the pricing model pushes you to use the product less.

Where the incentives actually align

So we came back to the question: where do our incentives and customer incentives actually overlap?

The answer: value delivered over time.

As your company grows, you need more from your revenue infrastructure. More complex contract structures. Revenue recognition that holds up under audit. Commissions that calculate automatically when deals close or contracts change. Integrations across your accounting, CRM, and payment stack.

The value you extract from the platform increases as your operational complexity increases. That's where ramp pricing comes from.

Year 1: $500/monthYear 2: $1,000/monthYear 3: $2,000/month

Full platform access. CPQ, billing, revenue recognition, commissions. All integrations. No caps on contracts or customers. Month-to-month commitment.

The price increases because the value you're extracting increases. Not because your revenue increased. Because the platform is handling more operational complexity, eliminating more manual work, connecting more pieces of your revenue operations that used to require reconciliation.

Year 3 pricing is still less than one full-time employee. By that point, the platform is replacing what would otherwise be multiple people's worth of spreadsheet work, manual calculations, and month-end reconciliation.

And critically: there's no incentive to route deals outside the system. Your biggest enterprise contract costs the same to process as your smallest one. The pricing model supports using the product the way it's designed to be used.

For larger companies with more complex needs, white-glove onboarding, dedicated support, or custom integrations, we offer custom pricing. Same platform, different scale, different expectations.

Why month-to-month matters

Here's the part that changes the incentive structure entirely: no annual contracts required.

Month-to-month at every tier. If the product isn't delivering value, you can leave. If your business has a down year or revenue stays flat, your price doesn't automatically increase. We're not taxing your struggle.

This only works because we're self-funded.

VC-backed companies need to capture revenue now to hit the metrics that unlock the next fundraising round in 12 months. Annual commitments, aggressive discounting, land-and-expand pressure. These aren't accidents. They're features of the incentive structure.

You lock in annual deals because committed ARR looks better on a fundraising deck than month-to-month revenue. You optimize for revenue capture over value delivery because the next round depends on the growth story, not the retention story.

We have over three years of runway. No board pushing for faster growth. No fundraising deadline forcing short-term decisions. Which means we can price for long-term retention instead of short-term revenue capture.

Month-to-month forces us to keep earning your business. The product has to justify the price every month, not just at renewal time. That's the deal.

The bet we're making

We're betting that if we build something that actually works, that handles your operational complexity, connects contracts to invoices to revenue recognition to commissions in one system, and stays predictable as you scale, you'll want to keep using it.

And if we're wrong, you can leave. Month-to-month means the product has to keep earning it.

This is what happens when you start with the question: where do the incentives actually align? You end up with pricing that's transparent, predictable, tied to the value you're getting, and designed so that using the product more makes it more valuable instead of more expensive.