Only two paths for CFOs (middle is over)
The CFO is the AI secret weapon. OpenAI is guaranteeing PE firms a 17.5% return. What’s worth anything when super intelligence becomes free.
Every day feels like the world is changing with AI.
The middle ground in finance is gone.
I spent this week working with my small CFO research team, focusing on three things that changed how I think about the future of finance.
Chamath Palihapitiya asked a question on the All-In Podcast that no CFO wants to hear in a board meeting. “If super intelligence is coming, what is anything worth?”
OpenAI just offered private equity firms a guaranteed 17.5% minimum return to help them deploy AI across the companies they own. When the flagship AI company is guaranteeing returns to PE, something fundamental is shifting.
Fortune published a study showing that when CFOs lead AI projects, 76% achieve real value. When anyone else leads, the results collapse.
In today’s letter I connect all three and tell you what it means for your budget, your team, and your career.
If you’re a CFO, Controller or FP&A manager... this is highly relevant to you.
Let’s dive in.
Chamath just asked the question your board is thinking but won’t say out loud
On this week’s All-In Podcast, Chamath pulled up a chart showing how many years of free cash flow it would take to earn back one share of stock.
Snowflake: almost 100 years in 2023. Now cut in half. ServiceNow down 31% in 52 weeks despite strong AI adoption. Workday at 3.3x revenue, the cheapest it has ever traded. Stock down 49% in a year.
But Apple, Microsoft, Meta, and Alphabet? Walking up.
He said the market is telling you these cash flows are “monopolistically durable.”
The market is splitting in two. Companies the market believes AI cannot disrupt are getting more expensive. Everything else is getting repriced like it might not exist in five years.
Then he said something that should change how every CFO models long-term value:
If AI lowers the cost of disruption so dramatically that no company can credibly project free cash flow beyond five years, equities would need to get repriced not as discounted streams of future cash flows, but as a multiple of what they generate right now.
He compared it to NYC taxi medallions in 2011. Worth over $1 million each. Then Uber arrived and they dropped below $100,000. The cash flow projection didn’t change gradually. It collapsed because the underlying assumption about durability was wrong.
Goldman Sachs published a note this month projecting that by 2030, more than 60% of software industry operating profit could migrate to AI agent systems.
Every SaaS contract on your P&L is now in question. The average enterprise wastes $19.8 million a year on unused SaaS licenses (Zylo 2026 SaaS Management Index). AI agents at $20/month can now replace categories of software that cost $50,000 a year per seat.
David Sacks, who just became co-chair of the President’s Council on Science and Technology, confirmed it on the same episode:
As a SaaS investor, it was an apocalypse. My exit comps were affected.
a16z published an essay this month called “There Are Only Two Paths Left for Software.” The argument: every software vendor must either grow revenue 10%+ faster through AI-native products or rebuild to 40%+ true operating margins. Everything in between is “no-man’s land.”
If you’re renegotiating vendor contracts in the next 90 days, you have more leverage than you’ve had in a decade.
Use it.
OpenAI is guaranteeing PE firms a 17.5% return
This is the most underreported story in finance this month.
OpenAI offered private equity firms a guaranteed minimum return of 17.5% through a $10 billion joint venture. TPG anchored it. Advent, Bain Capital, and Brookfield joined
The deal works like this: PE firms commit roughly $4 billion in preferred equity with board seats. OpenAI guarantees a 17.5% floor return. In exchange, PE firms deploy AI across their portfolio companies and drive the adoption that OpenAI can’t do alone.
MIT found that only 5% of enterprise AI deployments achieve measurable business results. The estimated waste: $30 to $40 billion. McKinsey’s own data shows 88% of AI proofs-of-concept never make it to production.
That’s why OpenAI is doing this.
The technology works. Adoption doesn’t. And the fastest way to solve adoption is to put AI inside companies that a PE firm controls top to bottom.
Sacks explained it on the podcast:
They’re betting they can own the change management around AI. Everyone assumes you throw AI over a wall and a business automatically knows how to use it. What we’re seeing is it’s pretty difficult.
If your company is in a PE portfolio or could be acquired by one, the buyer is already modeling what your operations look like with AI agents doing 30-40% of the work. OpenAI is literally paying to make that happen faster.
If you’re a CFO at a mid-market services firm, someone is modeling what your company looks like with 40% fewer people and AI-driven operations.
And they’re putting a bid together right now.
The CFO who leads AI wins
Fortune published a study that I think is the most important data point in this entire newsletter.
Only 2% of companies have their CFO charged with driving AI value.
But when they do, 76% achieve a great deal of value. Far higher than any other C-suite role. Higher than CDOs. Higher than Chief AI Officers. Higher than CTOs.
The CFO is the AI secret weapon.
And almost nobody is using them.
DBS Bank is one of the exceptions. They put unit CFOs in charge of vetting every AI number. The result: $1 billion Singapore dollars in economic value from data analytics and AI.
Adobe is another. Dan Durn runs finance, technology, security, and operations. His team deployed AI agents across 19 inboxes. 300,000 emails automated. Contract review time cut in half. 5,000 hours saved. Adobe’s AI product revenue tripled year over year.
And Dan Durn warns.
If finance doesn’t adopt AI, it becomes a rate limiter of growth.
The gap between intention and execution is where careers are made.
