Jim Cook is the full-time founder & CEO of BenchBoard.com, a strategic advisory and executive coaching company. He also writes weekly at Cook’s PlayBooks, a Substack for founders, CEOs, COOs, and CFOs focused on lessons learned from scaling companies from series A to IPO. This article is brought to you in partnership with Brex.

Over the last 30+ years post-QuickBooks, we’ve been slowly patching together point solutions in an attempt to move finance teams from the back office to the front office, from delivering a finance report to having a seat at the decision-making table.

The first era of our finance stack evolution began shortly after the dot-com bust with Web 2.0, when we started digitizing everything. At the time, we were just happy to move away from paper-based workflows and file drawers filled with invoices and contracts.

It’s during this era that we saw the rise of Bill.com, which literally began with a tagline of “No Paper CFO.” Bill.com’s original simple idea? A cloud-based digitized invoice approval system that synced back to the new ERPs of that day, NetSuite and Intacct.

Below is a screenshot from a webinar I led with Rene Lacerte, founder and CEO of Bill.com, circa 2012. Read the bullets carefully to give you a sense of how we started and the basics we were solving:

On that webinar, I delivered one of my personal mantras with this quote:

“Don’t just digitize and automate the work. Understand the ‘real job’ the finance team is trying to do and design from that end goal backwards to the data entry screens of both the finance team and our other end user customers.”

The next era (roughly 2014-24) moved from Web 2.0 to the cloud and involved building better-than-ERP sub-systems in a clean, app-based design … but still syncing back to the ERP.

These were still point solutions requiring multiple integrations, learning curves, and data silos. In this era, our financial data became more accessible, faster to retrieve, and easier to communicate.

This era gave birth to many of the solutions we use or are still using today, with companies like Expensify, Navan (formerly TripActions), Carta, Anaplan, Adaptive, Runway, Datarails, and of course, Brex.

Over the last 12 months (2024-2025), I’ve been writing and speaking about the third era of finance technology we’ve now entered. It’s clear to me and many others, we are witnessing a classic technology inflection point where powerful new capabilities create exponential efficiency and productivity.

We now have the opportunity to architect a new AI-first finance stack and to finally cement our seat at the strategic and operating decision-making table.

The vision for the AI-first financial OS

• AI that's fully API-integrated with all other company subsystems
• Creating a new real-time finance data layer = our modern system of record
• Designing AI-structured intelligence, collaboration, and prompts (questions/answers) into this layer
• Finance leading strategic recommendations and course-correcting decisions in using human language as our “code”
• A human finance team of experts managing it all — our new financial architects and financial orchestra conductors of our new AI data layer servicing the business (the rest of the company)

Our new finance OS should not be thought of as just another new software technology. We have to make the mind shift to:

• Designing human + AI financial agents
• Designing finance decision engines
• Leading the business with powerful new AI-first workflows

Specific use cases across the org:

• Marketing: Make advertising campaign recommendations to improve CAC (Customer Acquisition Costs) and LTV (Lifetime Value of the Customer) in partnership with the chief marketing officer.
• Product: Make PLG (Product-Led Growth) recommendations based on detailed revenue analysis of where our growth is actually coming from, so we can partner more deeply with our chief product officer
• Revenue: Right-size and optimize our revenue team staffing model and maximize “Rep Ramp Time” cross-functionally with the chief revenue officer
• “Roll Your Own:” [Insert your use case here]

We’re still very early in executing the vision

Ok, so if this is the vision of our future finance OS, where are we today?

In all honesty, we are very, very early. As in first inning early. While surveys report 95%+ of CFOs recognize the value and potential of using AI, other survey data clearly shows these are only small experiments or pilot programs with only 9% having deployed AI broadly across real workflows.

When I read the May 2025 Brex Benchmark, one of the key takeaways for me was that startups are spending more with Anthropic's Claude than with OpenAI's ChatGPT. This was more evidence that finance leaders are choosing AI tools based on reasoning capabilities and strategic analysis, not just automation. To me, it’s also evidence that we’re searching for the foundations of our new financial OS.

Every great product ever built has always started with a well-defined problem and iterates the solution(s) with deeply integrated end-user/customer feedback loops.

A few quick actions finance leaders can take as first steps:

• One-hour, weekly AI learning labs (what I learned, what I tried, what I improved)
• Innovation-based finance team hackathons, borrowing the playbooks from our product and engineering peer teams.
• Launch a small AI experiment internally within the department and learn, relentlessly

Our first customers need to be our own teams. Confidence and creativity will increase inside our teams with repetition. The goal is to build a good foundation that elevates the team’s learnings into higher-friction workflows to service our finance team's customers (other partnered departments) at higher and higher levels of strategy, decisions, and execution.

Want to be really bold as a finance leader? Hire a new position and call it “Vibe Finance.”

To really bring the point home, here’s Jensen Huang, CEO of Nvidia, from July 24, 2025:

Jensen went on to say the following shortly after:

"If you're not using AI, you're going to lose your job to somebody that uses AI. That we know for certain."

This isn't about replacing humans. It's about AI-enhanced humans replacing those who refuse to adapt. The window to position yourself is closing fast.

Our new game: the AI-first financial OS

So, that’s where we are today; the early innings of a new technology revolution.

The mid-game (2-3 years from now) will be finance-led decisions across the entire company using the finance team’s new data layer + AI agents. Then, we will level up our current finance team to be the architects and orchestra conductors of this new information flow.

The end game (3-5 years) will be "Finance as the OS of the company."

While the finance team has always emphasized the importance of being the business’s centralized operating system, most of us haven’t been delivering a winning game. We’ve been mostly stuck simply trying to get on base and score a few runs. We’ve celebrated “being better than Excel” as winning, and we’ve celebrated being better than NetSuite’s built-in ERP modules.

It’s time to invest much faster and bolder. It’s time to build. This time, it’s critical that the finance team “closes” the game and becomes the winning pitcher.

Build AI-first products that think like the C-suite

Start your build with products from companies that share this AI-first vision and are proving it with every new product release.

Make sure every product you design, build, or buy has three fundamental features:

1. Is built with the C-level in mind: Can your product/system answer the Top 10 C-level questions they ask of your finance team?
2. Offers “give/get” network leverage: The product is built with partnership/network leverage with a “give/get” mentality. Departments use the product to “give” key information and insights; they “get” their answers quickly and get back to building/operating the business.
3. Increases confidence and decreases risk with every “next decision”: Build AI into your data streams and systems of record to both scorecard your last decision and simulate your next one.

If not you, then who?

As you can tell, I’m excited for finance leaders to finally earn our seat at the table as the architects of a new, intelligent business operating system using technology that finally exists to “Make it so!” … our “5-year Mission” .… “To Boldy Go …” (couldn’t resist the Star Trek geek in me).

CFOs already touch and capture every part of a company’s data and decision stream, from hiring to pricing to procurement, sales quotes to cash, RevOps to DevOps, campaigns to capex to cap tables.

If not now, when?

We are uniquely positioned to finally integrate all the company’s data into an intelligence platform and connect the dots and decisions others simply can’t. Technology is no longer a barrier to entry. Everyone is a designer and coder now. Now is the time. Every day you delay this new build is one more day you are falling behind.

Jim Cook was Intuit’s first head of finance and helped lead their IPO (1993), multiple M&A’s, and scaled their finance teams and systems to a +$4B valuation. He was a founding team member of Netflix, designing all finance and operational functions of the DVD envelope era. Jim also served as CFO of Mozilla. With its 2004 Firefox launch with $2M nonprofit funding to over $500M revenue and cash balance, the Mozilla team re-created the browser market and the subsequent browser wars. During his 30-year career in Silicon Valley, Jim has served as advisor to founders, CEOs, and boards and remains extremely active advising the new finance leadership stack of companies at the forefront of our future — including Brex.