🚀 Back in Your Inbox & My Take on Claude for Small Business | The AI CFO

Heyo! My writing fell off the map in May, for a combination of personal & work reasons. On the personal side, I bought my first house here in Austin (!), which has been so much fun but also incredibly overwhelming.

June 5, 2026
The AI CFO

Heyo! My writing fell off the map in May, for a combination of personal & work reasons. On the personal side, I bought my first house here in Austin (!), which has been so much fun but also incredibly overwhelming.



At airCFO, we're halfway through a 7-week AI Enablement Sprint that is consuming the bulk of my hands-on-keyboard time. The goal of this sprint is to rebuild airCFO's operating cadence from the ground up around AI, and I think we're going to blow people's minds once we pull everything together. Much more to come here as we start shipping AI workflows into production.



While my writing cadence slowed down in May, the AI world certainly did not - on to this edition's content:

💡 My Thoughts on Claude for Small Business

AI CFO Essay Jun 4

Anthropic launched Claude for Small Business to a lot of fanfare. The pitch is pretty simple: 15 pre-built skills and agentic workflows, 5 built-in connectors to the tools you already use, toggle it on and Claude takes the late-night work off your plate.



I've had multiple founders forward me the announcement asking for my take, but the reality is more complicated than the LinkedIn posts would have you believe. What it attempts to do and what it actually does are very different things. Read the full essay over on LinkedIn.

🫀 The Ecosystem Pulse


(Podcast) Anthropic's CFO on Compute, Scaling to $30B ARR, and the Returns to Frontier Intelligence | Krishna Rao on Invest Like the Best


The most important number at the most-watched company in the world isn't gross margin or CAC, it's return on compute. Anthropic's CFO just reframed the entire AI P&L around a resource that moves between R&D and COGS in the same day, and every AI-native finance leader is about to have to learn to think the same way.



(Article) Ramp Stack: Built in the Room Where the Work Actually Happens


I'm not a neutral observer here: airCFO was one of the design partners on Stack, and our very own Johannes is quoted in this article (!). But it's an interesting look at how Ramp is viewing the future of the accounting space, partially informed by our team.



(Podcast) The AI Paradox: More Automation, More Humans, More Work | Dan Shipper on Lenny's Podcast


Easily the most quotable podcast I've listened to the past few months. Dan Shipper packs a contrarian take into every five minutes. The headline for finance people: "automation is a lie," and he means it as a compliment.



🤝 airCFO Content Connection


Claude Cowork Webinar

Most operators don't realize how close they are to automating the workflows that eat up their week. On June 24, I'm hosting a free 45-minute live session where I'll show you exactly how to connect your back-office tools to Claude and build that in real time. This week's essay is a great primer for this session.



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



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✍️ Written by Alex Wittenberg, CEO of airCFO

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