Brex's Third Chapter: Building The Intelligent Finance Future

The following piece is written as part of the Mostly Metrics Partnership Program.

As you've probably realized, I think it's cool to be a fan of business. I'm closer to if Bill Simmons ran your company's FP&A group than Anderson Cooper breaking news.

As such, every once in a while I'll get so jacked up by a company's story, and how they're transforming how CFOs do great work, that I'll be inspired to write a thoughtful deep dive on how they got to where they are today.

In my humble opinion, no company is more worthy of a deep dive than Brex.

Writing this piece felt full circle - Brex was my first ever ad sponsor. Me and their Chief Business Officer Art Levy bonded over fintech valuation multiples and deep cuts from HBO's The Wire in late 2022.

Flash forward three years and we’ve partnered on a bunch of stuff together. They were also the first one to put up their hands and say "I believe in you" when I went full time on Mostly metrics. And that should come as no shock. Brex excels at building deep relationships with people, and helping them thrive. This piece is an output of that dynamic.

If I had a lawyer, they'd tell me to tell you that none of this is investment advice (I guess, how could it be, since they’re a private company). Oh, another disclosure... I’m a (happy) Brex customer. It's what we run my thriving media empire on.

Brex is doing something unusual for a private company: they’re showing their work.

Over the course of the summer, I sat down with founders, executives, and customers to get a glimpse into their next chapter.

At a time when most late-stage startups from the 2021 era are in the fetal position (dumping costs and praying no one checks that forecast from the board meeting six quarters ago), Brex is opening up the books and showing exactly how they’re accelerating (at scale).

They’ve gone from Y Combinator darling, to COVID-era wunderkind, to enterprise heavyweight. And the numbers back it up. Recently reaching approximately $700M in total gross annualized revenue, while growing nearly 50% YoY, Brex isn’t just staying alive. They’re compounding.

We know this to be true because they’re a company with GMV retention above 115%, and CAC Payback Period under 16 months. That’s top quartile, perhaps even top decile, for their size and stage.

And what’s more impressive than the metrics is the intentionality behind them.

This isn’t a company clinging to product-market fit. It’s one that made hard calls, flattened its org, rewired its GTM motion, and set itself up for a successful third act.

Brex isn’t the loudest company in the group chat. But they’ve certainly got the receipts.

Brex started with a card.

That might seem quaint now, but in 2017, offering a virtual corporate card wasn’t just a feature; it was (quite literally) rebuilding the wheel. It’s now something we take for granted.

Remember: there was no Marqeta. No Stripe issuing. If you wanted to launch a card product, you built your issuer-processor from scratch.

And Brex did, spending two years developing their own.

Which, yes, was really fucking hard. But doing hard things is, like, a moat.

As Pedro, Brex’s founder explained to me,

And in the age of AI shortcuts, that kind of foundational infrastructure has only become more defensible.

Realizing that the global payments ecosystem is fragmented, complex, and full of gatekeepers, Brex’s decision to roll their own stack has aged well.

Brex’s CTO James Reggio told me,

In short: the financial ecosystem is impervious to shortcuts.

Looking back, the founders, Pedro Franceschi and Henrique Dubugras, were barely into their twenties, fresh off their last startup. But they had already seen how broken corporate finance was for startups. If you were a two-person team with a big idea and a Delaware C-corp, your best corporate card options were… IDK, basically a Best Buy gift card. Big banks and AMEX wanted five years of credit history, all sent via fax machine.

It was the classic paradox:

Founders were expected to show revenue, a huge cash balance, and a personal guarantee… just to buy their team a few pizzas on plastic.

Brex flipped the script. No personal guarantees. No credit checks. No elevator hold music. Just data. They underwrote based on real-time cash flow, and you could get approved before Amex finished playing you that same flute loop from 2004.

Brex understood their early customers because they were their early customers.

That context shaped everything: the tone, the design, the onboarding. Brex didn’t look like a bank (which, my imaginary attorneys remind me, I’m legally required to say they are not). It looked like Stripe for spend. Shopify for CFOs. In a world of sterile banking UX, Brex hit different.

The card got them in the door. But even then, they weren’t building “just” a card company. They were laying the rails for the modular financial operating system. The card was simply the shortest path to get a foot in the door.

The early momentum was electric. Within 16 months, Brex went from zero to $100 million in revenue. That translated into Brex serving 1 in 3 venture-backed US startups today, from two-person seed rounds to more than 250 publicly traded companies.

That trajectory is bonkers, even by today’s AI hypergrowth standards.

The startup world anointed them a fintech golden child. Valuations soared. Competitors emerged. Expectations compounded.

But as any best selling musical artist will tell you, success has a shadow.

What made Brex special in its first act, its ability to move fast and build products for companies just like them, would eventually collide with the very companies it aspired to serve next.

And the funny thing is that much like their first act, they had to become that very company to transcend to the next level.

For a long time, speed was the strategy.

Brex moved fast, shipped faster, and won logos on energy alone. We’ve all hooped with that freak athlete who jumps out of the gym and plays on sheer momentum.

That was Brex. Startup DNA. Engineering horsepower. Contrarian confidence.

But speed has diminishing returns. Eventually, you need a left hand dribble.

The product surface area kept expanding, but customers weren’t always sure what changed. Internally, Pedro, their CEO, noticed something was off: R&D was ramping, but the user experience wasn’t compounding. In fact, parts of the product had become harder for earlier customers to use. Going from one product / one audience to a multi-product, multi-audience brand is really fucking hard.

A tough lesson: Enterprise customers actually don’t want your product constantly changing. Companies do not like when you are changing your tech all the time. Yes, they like innovation. But they want it at a pace they can realistically absorb.

Meanwhile, the GTM org had thickened. CAC was creeping up. Incentives around what to lead with, cards or software, were muddy. The roadmap had grown, but focus hadn’t.

You could argue Brex was losing touch with their core identity, but they weren’t losing a lot of deals. They were still growing more than 30% per year.

No. They hadn’t lost product-market fit. But they were cosplaying a version of an enterprise company they thought they should be.

As Chief Business Officer Art Levy put it:

To be more specific, in addition to promoting the best IC’s, they removed two layers of GTM management. They shifted from constant shipping to three major product drops per year, each one coordinated across multiple teams. They went back to the studio to make an album that sounded like the Brex of 2017, while at the same time showing that they too, like their audience, had grown up a bit.

It was a reset on how deliberate they were in bringing products to their customers.

Promoting from within is a core value Brex embodies today. Brex doubled down on a builder culture, putting top individual contributors in leadership roles, not just folks who managed well on paper.

In the words of Pedro:

Founder Mode didn’t just apply at the top; it showed up across the org.

And that’s the paradox Brex leaned into: scale by trusting the people closest to the work.

By their first coordinated product release in mid 2024, it started to click. The roadmap got tighter. Reps got clarity. The customer journey got smoother.

Brex had built a brand on speed. Now it was humming in a clear direction.

As Pedro told me, when you want to build something enduring, extreme clarity is a super power.

In enterprise, going at it alone is a choice. And usually, it’s the wrong one.

And to partner well, you have to know what’s truly core.

For Brex, that means infrastructure: card issuing rails, expense policy logic, global payment flows. The stuff that makes or breaks payment reliability. The kind of foundation where being the system of record for expenses actually matters.

Everything else? They partner.

Art Levy, Chief Business Officer, put it plainly:

Take Zip. Instead of building their own intake-to-procure flow, Brex embedded with them. Same with Navan for travel. These aren’t superficial deals. They are deliberate product partnerships, built on-site with 10 engineers per company working side by side for six months. The go to market motions fall into place afterwards.

And it’s working. Brex now wins 85%+ of upmarket competitive deals, many sourced through partners. It's not just about who you work with, it's about who drives you to the meeting and the close.

Companies like Canva, Anthropic, and Datadog now run enterprise travel and spend management through Brex… without Brex becoming a travel company.

In the words of their CTO James Reggio,

And their customers agreed. I spent time with Ken Liu, the first accounting hire at high-growth security startup Huntress (last valued at $1.5 billion). They replaced AMEX with Brex five years ago, and have expanded the product suite over time.

As any financial operations pro will tell you, the two most important integrations to nail with your expense management platform are procurement for big ticket items and travel, especially as the value of IRL increases. Ken’s team is in the midst of implementing Zip to bring the Brex integration story full circle.

And that’s the discipline. Brex doesn’t want to be your everything. They want to be the thing everything else plugs into, more akin to the nervous system than the whole body.

While they’re not the system of record in the traditional ERP sense, they very much are when it comes to expenses. Ken again,

The benefits of the partnership are evident: over 53% of upmarket wins in the last six months were partner-led or sourced.

As Pedro told me,:

And this might be where Brex shows the most maturity.

Like Microsoft in its prime, they realized the leap from prosumer to enterprise doesn’t come from brute force. It comes from leverage. And leverage often wears a partner badge. The fastest way into a Fortune 500 isn’t always through the front door. Sometimes it’s being bundled into the system that makes other systems better.

Here’s the nuance:

Some of your best partners will eventually become your competitors.

That’s not dysfunctional. That’s gravity. In tech, everyone goes horizontal… eventually. Features become products. Products become platforms. The Venn diagram closes whether you like it or not.

Brex gets that. They’re not naïve. And they’ve made peace with it. In fact, they’ve embraced it.

In many ways, Brex’s modularity is its strength.

They know that being indispensable now is more valuable than trying to own everything later. If a partnership gets customers to value faster, even if it introduces future overlap, they’ll take that trade.

People love to talk competition. But few talk about the size of the actual opportunity. Often the narrative focuses too much on the characters - who’s beating who - rather than the prize itself.

Brex is more than halfway to $1B in revenue, yet still under 1% penetrated in its core TAM.

Not only is global payments one of the largest markets in the world, Brex is uncovering white space opportunities to put increasingly more on cards. For those following along at home, take out your napkin and pen:

Brex has to win just a tiny, single-digit percentage to grow extremely quickly.

And that doesn’t even include the incremental $200B+ in commercial card TAM unlocked by their move into the EU.

In terms of how the company makes money, they are monetizing mainly through card interchange today, but companies are choosing them because of the software.

If they were just another run of the mill corporate card issuer, they wouldn’t be as well positioned to increase spend. Customers are choosing Brex for their software, even though they are being monetized through their spend.

And that allows them to monetize at a rate of 10x what legacy expense management systems can, since it’s a more valuable revenue stream with higher upside than just generic software.

And unlike some of the laughable TAM slides we’ve all seen, this one holds water.

Not all companies have revenue, but all companies have expenses.

Brex has built three moats that actually compound:

As we’ve established, Brex was the category creator: financial services and financial software were in two different places before Brex.

You’d have to choose between giving everyone a corporate card and not knowing what they’re spending it on, or putting everything through procurement, and grinding the org to a halt.

When you break the tradeoff between speed and control it actually results in more spend, and those moats make money. Brex ARPU now stands at +$2,000. To put that in perspective, that’s rumored to be double digit multiples higher than legacy spend platforms like Expensify or Bill.com.

That trifecta is rare. And it sets the stage for their next act.

Brex has already moved from

What comes next?

Imagine Brex as the system of record, the place where all transactional data lives, and agents from Zip or Navan taking actions on top of it.

They’re already building APIs and interfaces for third parties to trigger spend actions, route approvals, and automate tasks. Internally, Brex is rolling out seven distinct AI agents, from receipt review to policy enforcement, aiming to automate every financial task from swipe to close.

Brex is quietly turning into the control plane for modern finance. We just weren’t paying attention.

Brex shouldn’t still be winning.

Not if you look at the cohort they came up with.

The 2017 draft class has more Markelle Fultzes than Jayson Tatums… startups that lost their jump shot instead of extending their range.

Brex evolved.

Not without lumps. CAC crept up. Org charts got bloated. The product moved perhaps too fast for users at times.

That’s what makes this third act compelling. Not just the numbers (seven products, two greater than $100M in revenue). It’s the posture.

Brex is durable. Just like it’s (owned) infrastructure.

Enterprise-grade rails, with taste. Modular workflows that don’t feel stitched together. Brex is now active in 200+ markets and 60+ currencies. Just like Pitbull, they’ve become Mr. Worldwide.

While not an ERP, it’s not a stretch to say Brex is the source of truth when it comes to expenses. Ken from Huntress told me as much:

It’s a quiet but powerful signal that Brex isn’t just sticky. It’s essential. And how you control your own destiny.

Brex is a company that still acts like IC builders, even while serving customers worth over a trillion dollars (they won’t say who, but I asked. a lot… is it you?).

Now, there’s always that tension with success. Look at Drake. The guy got too big, too polished, and people started looking for reasons to dunk on him. That’s what happens when the climb stops feeling scrappy and starts feeling inevitable. Tallest poppy syndrome.

But Brex never made it feel inevitable. They made it feel earned.

They didn’t coast. They earned their way back into the conversation, with receipts (no pun intended) to prove it.

They’re not trying to be the loudest company in fintech.

They’re trying to be the last one you’d ever rip out.

As a student of the game, and CFO who’s experienced the changing expense ecosystem first hand, here are four takeaways that stood out from my conversations with Brex’s execs, customers, and long time employees:

1. Great partnerships thrive in grey zones. The world isn’t binary. You can partner and compete, often at the same time. Brex understands that building a scalable business means operating inside ecosystems you don’t control, while growing your own. The most mature teams are comfortable in that tension.

2. The enterprise CFO doesn’t live in an ivory tower. I’ve lived this first hand, trusting my controller to make tech decisions that best fit her workflow. There’s no single buyer who waves a wand. Purchasing decisions at scale are distributed, from AP to procurement to FP&A. Winning means delivering a clear “first win” use case and then expanding trust over time. Brex doesn’t sell to a job title. They win the room.

3. Not all customers are created equal. Brex’s main competitor has more logos, but Brex reportedly earns a rumored 4x the gross profit per customer. And in fintech, gross profit is the hill your valuation dies on. What’s more, Brex monetizes through multiple vectors: cards, software, deposits, and platform infrastructure. That’s not just diversified; it’s a durable platform.

4. ICs are worth their weight in gold. The best decisions don’t come from people who collect headcount. They come from those closest to the work. Brex leaned into this by promoting top individual contributors to leadership roles. Craft leads. Not title inflation.

Wishing you a corporate card that allows for both speed and control,

CJ