For years, the CFO workflow has been fragmented. Finance teams work across multiple tools, patching together systems for payments, spend management, banking, and reporting, relying on outdated products that were not built to communicate with one another. Once a company has landed on a system, switching is costly, leaving businesses stuck making do with products that only partially meet their needs.

That fragmentation has real consequences. From our conversation earlier this spring with CFOs across The Pritzker Organization Portfolio, we know that the CFO role has expanded, with many leaders owning workflows beyond finance, including IT, HR, and business development. Most of these CFOs are managing six to ten different finance software vendors, and the majority of respondents to our survey following our conversation shared that they spend at least five hours a week reconciling data.

But the financial software stack is beginning to change. AI is moving finance away from manual workflows and toward intelligent infrastructure that centralizes financial operations. Companies no longer want fragmented point solutions stitched together through siloed data and disconnected workflows. They want integrated platforms that bring spend, payments, reporting, and operations together in one place.

Flex is doing that and more. The AI-native financial operating system brings together business and personal financial workflows into a single platform, giving owner-operated, mid-market businesses full visibility and control over their finances and less operational complexity. Flex’s platform combines banking, finance workflows, and personal financial tools to serve as an all-in-one finance platform, rather than just another point solution. 53 Stations is excited to share our participation in Flex’s $70M Series B1.

Bringing finance under one roof

Flex is building the “full financial home” for owner-operated, mid-market businesses. These customers often own more than one entity and, in addition to managing those finances, are also managing their own personal financial life. Most software treats those worlds separately, further fragmenting operations. Flex’s AI-native operating system takes in data from all financial sources and automates workflows, connecting business and personal financial management. Its 3-in-1 card provides users cashback, rewards, and Net-60 float, a key differentiator in the market.

Legacy financial platforms were designed for either end of the spectrum: micro-businesses and large enterprises. Owner-operated, mid-market businesses have historically been forced to adapt to platforms that were never designed for how they operate. Flex is specifically building for this segment, creating a system designed for these business owners while eliminating the fragmentation that has long defined financial software.

Why We Invested

Beyond the company’s differentiated product vision, several factors drove our conviction in Flex, including the team’s deep understanding of the customer, CEO Zaid Rahman’s track record as a repeat founder, and the scale of the opportunity ahead.

The strongest companies are the ones building with data in mind so that their product best serves their customer. Flex identified cash flow management as a major recurring pain point for the kinds of businesses it serves, like a company that has to pay upfront to source goods before getting paid itself. Flex used this customer need as a signal and built its Net-60 float product as the wedge to solve it. Flex also rebuilt its infrastructure so it could function as its own bank, rather than rely on third-party banks. Why? Because bringing banking in house simplifies operations and gives them more leverage to serve customers.

As a third-time founder, CEO Zaid Rahman understands that aligning customer needs with company vision is key for success. He also understands what it takes to build and scale businesses. Zaid’s strong network and ability to recruit top talent across categories, combined with his proven track record of execution, are undeniable. As part of their news, Flex shared how much they are growing: ~4x year-over-year at a 9-figure annualized run rate and $10B+ in annualized TPV.

The market opportunity is also significant. As much of the financial ecosystem has been built around the needs of small businesses and large enterprises, the middle-market finance category is significant.

The broader shift underway in financial software is heading away from standalone products and toward unified operating systems. We’re excited to partner with Flex as they continue building the financial home for modern business owners.