Everyone assumes AI will replace bookkeepers first.

But here’s what I’m seeing in founder circles:

They’re keeping their bookkeepers.

They’re replacing their fractional CFOs.

With AI.

Why?

I was reading through a Slack group full of entrepreneurs and one founder nailed it: “Most CFOs don’t speak human. Claude does.”

That line says everything.

Because here’s the uncomfortable truth: AI is beating CFOs not on math… but on empathy.

Bookkeeping is still too messy to automate away — real-world transactions, vendors, inconsistencies. But CFO work? Reports, forecasts, “insights decks”? AI can generate those today, in plain English, instantly.

And more importantly, it will explain, clarify, re-explain, and never get impatient.

That matters. Founders don’t just want data, they want someone (or something) that makes them feel understood and that helps them understand…without judgement.

We already see people turning to AI as coaches, therapists, even romantic partners (uhhh…yikes). So should it surprise us that they’d rather ask AI about cash flow than risk feeling dumb in front of a CFO?

If AI “speaks human” better, what does that leave for the CFO?

Maybe the role shifts from storyteller to systems designer. From interpreting the numbers to architecting the data that feeds the AI.

So I'll throw this back to CFOs…. are you really that sure that your role is safest from AI right now?

photo: Hanging with Jamie Shulman - with whom I kicked around this AI / CFO disruption idea