🚀 The Jobs AI Won't Take and The Lost Meaning of ARR | The AI CFO

Last week I was in Salt Lake City for airCFO's annual company offsite. Over two full days of programming, we talked through our plan for overhauling our organization to leverage the AI superpowers we have at our disposal as of Q1 2026. These sessions were the culmination of a 4 month training we ran to increase our team's AI fluency, and it's really starting to pay off: 80% of airCFO team members are using Claude every day.

Over the next couple quarters, we'll start to see companies realize major ROI from integrating AI into their operations. I am confident airCFO will be one of these companies, and I'm excited to share our progress on the journey!

On to this week's content:

💡 What Happens to Accounting When the Buttons Push Themselves?

A couple weeks ago I put on Benedict Evans's "Another Podcast" and he happened to be opining on the exact topic that's been consuming me recently: how back-office employment will shift as AI proliferates knowledge work.

He compared the accountant role to the original 'button pusher' profession, the elevator attendant. One of these professions was completely decimated by technology, the other has thrived through multiple successive waves of change (take a guess which is which). Evans explores what this distinction says about the types of jobs that will be impacted by AI.

I evaluated his argument through the lens of the accounting & finance industry — check out the full essay on LinkedIn.

🫀 The Ecosystem Pulse

(Podcast) What jobs are AI jobs? — Another Podcast (Benedict Evans)

If you read the longform piece this week and want the original argument that started me down this road, this is the episode. Evans is doing the historical pattern-matching the AI labs aren't: looking at what actually happened to jobs in past automation waves, not what people predicted would happen.

(Social) Being Truthful And Precise About Revenue — Garry Tan

ARR has lost its meaning, and Tan is the first major voice trying to fix it. His pilot / bookings / revenue / recurring revenue framework is the measuring stick we need before we can tell which AI companies are actually thriving and which are fool's gold.

(Article) The Mental Mapping from Annual to Monthly and Usage-Based SaaS Metrics — Dave Kellogg

Subscription to usage-based pricing didn't just break our SaaS metrics. It broke the meaning of "recurring." Kellogg's 2022 post still does the cleanest job I've seen of pulling apart what we actually mean when we say MRR or ARR in a world where revenue varies month to month.

🔎 Tool & Resource Spotlight

The AI Daily Brief It's impossible to keep up with everything happening in AI. The AI Daily Brief is the one show I lean on five or six days a week to do the filtering for me.

🤝 airCFO Content Connection

Funded: Aileen Allen, Mercury Fund Aileen Allen from Mercury Fund stopped by to talk about building a defensible GTM in 2026. We got into why founders need to make the GTM hire earlier than they think, how AI can be a multiplier but only if there's a human in the loop, and why community-building should stay founder-led.

That's all for this edition of The AI CFO - we'll be back in your inbox soon with more musings on the future of AI-powered finance & operations. Please reply to this email directly with any feedback/suggestions/just to say hi!

Cheers,

Alex Wittenberg, CEO @ airCFO