Did you push that “Play” button at the top while you read this? I created that playing around with Google’s NotebookLM as I experiment and continue to immerse myself in all these new Ai tools vs simply talking about them. Hope you are enjoying that audio file. The email they refer to was from me. It was simply a copy/paste then “Generate Podcast” from my upcoming articles - I figured it’s a great preview.
CFO Roadmap Series Preview: From Operator to Architect
I’m now in my 4th decade of my CFO journey through Silicon Valley. Dozens of times I’ve been asked various forms of the following questions by Founders, CEOs, VCs, and even executive recruiters:
“Do you think I/we/this company needs a CFO?”
“When should I hire a CFO?”
“Who would be a great CFO for my company?”
“Do you have a good CFO job description?”
While the answers may seem straightforward, the real answers are actually a multi-variable equation consisting not only of “Who? What? When?” but also company stage (early, growth, late), the CFO capabilities required for each stage, and the considerations for industry and business model.
I’ve been asked to give a short keynote to help kick off the inaugural Operators Guild CFO Summit on March 19, 2025 in SF. So, no better time to do what I do and curate several of my “Best Ofs” on this subject and to reference some recent great articles from the likes of folks from a16z, BVP, the SecretCFO, and others. Most importantly, I’ll publish it all here for future reference.
“Write It Down!” is reverberating through my head - my own inner roommate I hear talking to myself - “Hey Jim, practice what you preach!” So here comes another in-depth 3-part series to unpack my brain, cement historical learnings, and to pay it forward.
The other benefit of writing it down publicly here on Substack is I will be able to add/edit this series with future learnings as the journey continues. Why not treat these Substack posts as continuous sources of upgraded learning?
I’m also excited to finally publish what I’ve been writing on whiteboards and hand waving for years in the form of a summary table of “CFOs By Stage” (Part 2 of this series) and to publicly publish for the first time my “CFO Scorecard” which pulls together many of my thoughts into a specific, actionable, weighted scorecarding template that I explain how to use in Part 3.
I know, I know, for all you finance people, operators and CFOs, I can already hear your excitement… “You had me at ‘CFO Scorecard!’”
Whether you're a CFO yourself, an aspiring one, a founder working with one, or an investor betting on leadership teams, this series is for you.
Below is a quick summary of the Series that begins Tue, March 4th.
Part 1: The 3 Past Eras of CFOs and The Next CFO Era
The role of the CFO has evolved dramatically over the last 30+ years. A year ago I keynoted a dinner talk partnered with Jeff Epstein, a highly regarded former CFO and Bessemer Ventures Partner, where I first introduced the concept of “CFO Eras.”
Part 1 digs deeper to provide the historical context of what I believe were three distinct CFO eras - from accountant to strategist to operator - and explore the defining characteristics of the next CFO era that’s emerging today.
Unlike the past eras of “CFO Evolution,” the next era of CFO I’m calling the CFO Architect. While we will still be required to lead, make decisions, and drive business value, this time it really will be different. This conjures up one of my all time favorite branding campaigns by Apple/Steve Jobs:
CFO’s? Thinking Different? Really? YES! It’s time.
Here’s a quick preview of the 3 part series
Part 1: Summary
The three historical CFO Era archetypes and why each era demanded different capabilities.
How technology has forced the historical CFO evolution. Today’s technological changes forcing the next era of CFOs starting in earnest in 2025 - and why CFOs who don’t adapt these latest technologies will get left behind just like past eras.
New CFO capabilities and mindsets required to separate great CFOs from average ones in the future.
Part 2: CFO Requirements by Stage of Company
Tuesday: March 11th
Not all CFOs are created equal, and venture-backed startups need very different CFOs at different stages. A CFO who thrives at the early stages of Series A-B can struggle mightily at Series C and later stages. And vice versa.
In Part 2, I’ll break down CFO Requirements by Company Stage and produce a great summary table for future reference:
CFO capability requirements at the early, growth, and late stages - highlighting what works, what doesn’t, and how CFOs need to evolve through these scaling stages.
The biggest misalignment mistakes founders and investors make when hiring a CFO.
How CFOs must shift their leadership style, priorities, and skillsets as the company scales.
Part 3: The CFO Scorecard – A Framework for Excellence
Tuesday, March 18th.
Now that we’ve discussed Who you need as CFO, What You Need, and When - How do you then measure a great CFO?
In the final Part 3 of this series, I’m publicly publishing for the first time my own version of a CFO Scorecard I created and versioned over the past 10+ years (after being repeatedly asked the same type of CFO questions by CEOs, VCs, Investors, and aspiring CFOs).
My goal then, and now, is to produce a practical scorecarding framework for assessing CFO performance across a few key dimensions: Leadership, Operator, Strategist, Communicator/Influencer, and IPO/M&A Readiness.
All operators love a great scorecard and this will be my pay it forward to anyone reading here. Whether you are an aspiring CFO, a CFO looking to benchmark yourself, a CEO evaluating your finance leader, or an investor assessing one of your key executives, this tool will provide a clear, structured way to define and measure CFO excellence by stage while allowing you to change the weightings of the capability requirements by stage of growth.
Learning from the Past: Leading the Future
The CFO role is no longer just about finance - it’s about leadership, strategy, structure, and execution. It’s about aligning short to mid term value creation and long-term value capture.
Great CFOs no longer just control and report the numbers - they must be right hand partners to the CEO/Board/Investors and a Business Coach to peer leaders and employees across the company.
We are quickly moving into the next CFO Architect Era driven by technology improvements. You will need to learn and incorporate these new skills to take your game to the next level.
Join me over the next three weeks as we dive into the making of a truly great CFO for the next era.
For Paid Subscribers of this newsletter, below is the full audio version of the upcoming series as created by Google’s NotebookLM - as I’m personally immersing myself into all these tools. It’s amazing how great a job tools like NotebookLM are doing.
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