CFO Roadmap Series: Scorekeeper to Operator to Architect Part 1

Historical CFO Eras; Predicting the Next Era of CFO

A few weeks ago as I was drafting this series, I was explaining to a friend how I’ve realized other executive roles in startups have evolved faster than the CFO role. I used HR as an example. I described the HR journey from what was mostly compliance and control in the 80’s and 90’s to how they graduated to “Chief People Officers”…. no longer “Resources for Humans”.

I then began describing other executive role evolutions. I realized there was a clear correlation between the software stacks specifically built for these operational functions and the corresponding rapid evolution and impacts these executive roles were making today. (Examples; Workday (HRIS), Salesforce, HubSpot, Clari, and GitHub; dozens of others)

We’ve seen the evolutionary leaps from VP’s of Sales and Marketing to CROs (Chief Revenue Officers) and CMOs (Chief Marketing Officers); Heads of Engineering became CTOs (Chief Technology Officers); Product Managers became Chief Product Officers.

CFOs? Well, we simply remained CFOs - the financial wizards behind the opaque curtain of excel-based financial reporting. We progressed much more slowly due to the fact that were mostly working with the same old systems (late 80’s Excel; 90’s QuickBooks; and 2000’s Netsuite). We played around with various dashboards and Anaplan and Adaptive for a while in an attempt to be cool but were forced to eventually port everything back to Excel. Only until very recently has there been a new exciting financial stack of tools on the horizon for the new Office of the CFO.(Vareto, Tabs, Puzzle, Brex, Ramp, and Runway) with many more AI tools coming.

Today, the CFO role, seeded by the promise of this new Office of the CFO platform stack, is on the precipice of our own rapid leadership evolution and corresponding leadership impact. It’s time to embrace the future of our new software+Ai platforms, quickly “Learn It” (new capabilities), “Do It” (install it), and “Coach It”, (communicate the benefits and impacts) to your own finance teams and executive peers.

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The Evolution of the CFO Role: A Historical Perspective in Three Eras + a Look to 2030

I first spoke about CFO Eras at a network dinner event a year ago (Jan 2024) where I partnered with my friend and colleague, Jeff Epstein of Bessemer Venture Partners and former CFO extraordinaire of Oracle, to give a keynote address to the CFO audience of about 50 people.

I described how the CFO role evolved over the last three decades - how investors, Wall Street, and other executives have viewed CFOs up until today. Looking back at that presentation, I realized I stopped a bit short and should have predicted the next era of CFO… and that’s what this Part 1 is all about.

My view is the CFO role has evolved over three major eras over the last 30+ years, each era defined by how companies have expected CFOs to create value:

1. The Scorekeeping & Reporting Era (1990–2005) - Compliance and Control

2. The Strategic CFO Era (2005–2015) – Partnering for Growth

3. The Operator CFO Era (2015–2025) - Driving Execution and Efficiency

4. The Next Era (2025-2035) – The Architect CFO: Designing Adaptive, AI-Driven Financial Ecosystems

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1. The Scorekeeping and Reporting Era: (1990–2005) – Compliance and Control

How CFOs Were Viewed:

• Seen primarily as financial stewards and risk managers

• Focused on GAAP accounting, audit readiness, tax planning, and regulatory compliance

• Investors and Boards expected CFOs to ensure clean books, no surprises, and predictable financials

• Wall Street’s View: CFOs were responsible for reporting, not storytelling—accuracy was key, but strategy was left to the CEO. Stock prices were rewarded quarterly on “hitting your numbers”. “Future Guidance” was not yet a “thing” that drove stock prices

Key Skills in the Scorekeeping and Reporting Era:

• Strong technical accounting knowledge

• Compliance & risk management expertise

• Financial reporting accuracy

“‘The Scorekeeper Era’ was all about simply putting the points on the board. The actuals. Numbers had to be clean… But there was very little forward guidance. And in fact, Wall Street incentivized stock prices based primarily on actual quarterly results. Future guidance in ‘90s conference calls were at the end of the call to simply set the bar for the next qtr. Today, future guidance is the stock price bar and presented at the beginning of the conference call. Future guidance is driving today’s stock prices…..the actuals for the quarter don't seem to matter a whole lot anymore.

Think about the last few conference calls you’ve listened to or watched on CNBC. Companies can miss their numbers, but as long as the future guidance is great, the stock price goes up after the conference call. The opposite also happens. Companies crush their actual numbers but soften their future guidance and their stock price gets crushed.

The CFO Scorekeeper Era was over by the mid-2000’s and we quickly evolved into the ‘Strategic CFO Era’ where you better be great at forecasting. You better be great at driving future metrics. You needed to be a better storyteller of the future starting around 2005 (the Strategic CFO Era) and that required a whole different skill set.”

Jim Cook - on CJ Gustafson’s Run the Numbers Podcast - Feb 2025

2. The Strategic CFO Era (2005–2015) – Partnering for Growth

How CFOs Were Viewed:

• Shifted from “Chief Accountant” and “Chief Scorekeeper” to Strategy Partner for the CEO and executive peers

• Investors and Boards expected CFOs to partner with the business and eventually storytell business performance, not just report the numbers

• CFOs were increasingly being asked to own the business model, pricing, unit economics, and understand customer lifetime value

• The Dot-com bust (2000-2002) and the Financial Crisis (2009-2011) created demand for CFOs who could recommend strategic decisions to balance revenue growth + cost discipline and create a “path to profitability”

• Wall Street’s View: The best CFOs were required to be chief investment officers who made trade-offs between growth, profitability, and efficiency and align the Company’s Strategy to it’s Execution

Key Skills in the Strategic CFO Era:

• Ability to influence strategy with financial insights

• Ability to communicate and storytelling the Business Model

• Right hand partner to the CEO, and key partner to the Board and Investors

• Chief alignment officer making investment bets/allocations based on separating the successful company activities from the unsuccessful ones.

“The great CFOs evolved from bean counters/scorekeepers to becoming the consigliere to their CEOs, the rare person in the org who could partner and make better decisions because all activities were connected to thed giant database system of record the CFO designed and installed. There was no other place in the organization that brought all this data together to make holistic recommendations and decisions other than the office of the CFO. CFO’s began to deeply partner with the CEO and their executive peers in the Strategic Partnering Era. I would say that lasted from, say, 2005 to 2015 when it was clear being a ‘Strategic CFO’ needed to once again evolve.”

Jim Cook - from CJ’s Run the Numbers Podcast - Feb 2025

3. The Operator CFO Era (2015–2025): Driving Execution and Efficiency

How CFOs Were Viewed:

• CFOs needed to not just own the business models but now were asked to hold the rest of the organization accountable to the key metrics, unit economics, and cash burn efficiency

• CFOs were now required to be Operating Partners and increasingly the “Internal CEO of the Company“. CFO’s of “No” were rejected. CFO’s of “Know” were required.

• Boards and investors expected CFOs to drive efficiency, not just analyze it

• Wall Street’s View: The best CFOs could build a compelling storytelling narrative based on key operational metrics to attract long-term investors

Key Skills in the Operator CFO Era:

• The best CFO’s of this era created and owned a Financial Philosophy and Investor Financing Roadmap of the business

• Who partnered with their fellow executives to create a deep operational understanding of the business

• Key designer of financial Data-Driven Decision-Making Systems

• Focused on connecting all other functional software stacks and subsystems/API’s into a clean Financial System of Record.

Key Context Over the last 10+ years:

• Post 2015, SaaS and subscription models became dominant – CFOs had to shift from “revenue recognition” to predictive analytics, LTV/CAC modeling, and ARR growth

• Rise of private equity (PE) playbooks – CFOs became the ones implementing PE-style operational rigor in growth-stage companies

• 2020s downturn (post-ZIRP era) – CFOs faced pressure to shift from “growth at all costs” to “profitable growth” and once again back to “Path to Profitability”

“In today’s CFO Operator ERA, CFO’s actually have to turn the dials, make clear recommendations, and take course correcting actions. CFO’s need to be working ‘in’ and ‘on’ the business.

Today, we are quickly evolving into the next era of CFO: ‘the CFO Architect Era.’”

Jim Cook - on CJ Gustafson’s Run the Numbers Podcast - Feb 2025

1 minute - Introducing the Operator Era:

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The Era of COO+CFO is Over: Ok… Ok… 2 more minutes! Another hot take:

4. The Next Era (2025-2035); The Architect CFO: Designing Adaptive, AI-Driven Financial Decision Making Systems

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