Attack the Float: The Power of Payment Terms

Rethink pricing before AI forces your hand.

As a CFO, one of the hardest challenges I’ve faced is connecting revenue to the actual value our product delivers.

Legacy billing systems weren’t built for usage-based or AI-driven models, and I’ve felt that friction firsthand.

Seriously… I’ve patched together some SKETCHY homegrown billing systems in my day.

That’s why I lean on Metronome’s Monetization Operating Model guide. It’s a practical framework to align finance, product, GTM, and engineering around pricing, packaging, and billing that scale. Whether you’re managing hybrid models or preparing for AI disruption, this guide offers concrete templates and lessons to get it right.

The following is a guest post from my other newsletter, Looking for Leverage.

It’s written for the C Suite running PE backed companies, and explores the playbooks successful companies have written in their pursuit of operational excellence.

If you ask ten product managers what they think finance can do to unlock innovation you’ll get ten different answers…

I was recently listening to Ben Thompson’s Stratechery podcast where he interviewed the CEO of Booking.com, Glen Fogel. Booking is the world’s largest online travel agency and the largest platform for booking accommodation. But it didn’t always start that way. It started as a company called Priceline. And they had to unseat a massive competitor in Expedia.

At the core of the discussion was the difference between an agency model and a merchant model.

In early 2000, the 800 pound gorilla was Expedia. They built their entire P&L around the merchant model.

How it worked was when you went to Expedia’s site, you put your credit card in to book a room and you were charged on the spot. Your trip could be five months out, but you pay for the deal you want right then and there.

The cash leaves your account and goes to Expedia’s account.

But here’s the catch - the hotel itself doesn’t receive their portion of the payment, around 80%, until AFTER the visitor shows up and stays.

Even worse, that payment might come another 30 days after the person stays.

Awesome for Expedia, as they can live off the float (ALL of the float, including the portion that’s not theirs to keep). Terrible for the hotels, many of which are small, family owned locations throughout Europe, who are dying from a cash flow perspective.

And the situation was even more dire if you were, counterintuitively, doing well.

Here’s how Booking.com attacked the float Expedia was living off, and unlocked billions in GMV.

Meanwhile, a much smaller company in Europe, Booking.com, was doing something completely different.

They used the agency model:

Booking never touched the customer’s money. They just matched supply and demand, and prayed the hotel would send them a check afterward.

This flipped the cash flow dynamic completely. Hotels loved it. But it was a nightmare for Booking’s own working capital.

Why? Because Booking still had to pay Google up front for the traffic, but wouldn’t see any revenue until weeks (or months) later, assuming the hotel even paid. And a lot of hotels just… didn’t. They’d ghost. No invoice system. No enforcement. No float. No leverage.

So Booking was stuck. Great model for growth. Terrible model for cash.

In 2005, Priceline (which had also started out with its own quirky merchant model) acquired Booking.com. Most companies would’ve swallowed the startup and forced them onto the parent’s system.

But Priceline did something smarter. They leaned into the agency model.

Why?

Because even though it was painful in the short-term, the agency model let Booking scale way faster on the supply side.

Hotels didn’t need a formal agreement. No prepayment. No crazy systems. Just upload your photos, set a price, and you were live.

The merchant model was a cash machine, sure.

But the agency model was a growth engine.

The dirty little secret of marketplaces is that supply-side scale unlocks everything.

But you can’t get there if your model slows down supplier onboarding. And that’s what the merchant model did.

Booking grew fast because their terms were friendlier. And once they hit critical mass, and had actual negotiating power, they started reintroducing merchant-style flows selectively, where it made sense.

Today, more than 15% of Booking’s revenue comes from merchant-style transactions. The difference? They have the scale, data, and infrastructure to handle it now.

This isn’t just a travel industry story.

It’s a playbook for anyone building a B2B marketplace, embedded fintech layer, or multi-sided platform. And the big unlock is this:

Too many companies let finance figure this out after the fact. But the best operators design it up front.

Here are a few lessons I took from the Booking story:

When people ask me what gives a company leverage, I usually talk about operating metrics: pricing power, retention, margin expansion, CAC payback.

But payment terms? That’s leverage in its purest form.

Leverage is controlling how money enters and leaves the building to your advantage.

Cash flow timing changes the way a business feels to everyone in the value chain, and when you get it right, it’s not just a finance decision. It separates first place from second place.

Booking.com figured that out. The question is: have you?

Chad Gold, seasoned CFO with stops at Salesloft, G2, and now FullStory, joins the podcast to talk about the state of the private markets, and the nuances of pricing and packaging.

On this episode we discuss:

Kyle Poyar and I launched a new podcast. It's called "Mostly Growth"

This week we jam on:

I’ll be at the Spendflo AI summit on October 18th. It’s at 12 PM EST.

I’ll be hanging out with my friend Sid Sridharan, Spendflo’s Co-founder and CEO, and giving a brutally honest take on:

Wishing you stern, yet fair, debt covenants,

CJ