28 February 2026 · LinkedIn
When markets reward a particular kind of announcement, leaders find ways to make it. That's what concerns me about what happened at Block this week.
Jack Dorsey announced that Block is cutting 4,000 roles - roughly half its workforce - citing AI as the driver. AI-attributed headcount reductions aren't new, and some have been quietly reversed. What is different this time is that the stock jumped 22%.
I've been watching that 22% carefully.
The market's logic is clean enough on paper. If you can do the same work with half the people, your margin improves, your valuation rises, the shareholder narrative writes itself. Dorsey frames this as leadership - other CEOs, he says, will follow. On that prediction I suspect he's right, which is what worries me.
I do find myself questioning whether Block's cuts are genuinely AI-driven in the way he implies, or whether AI has become the most defensible rationale for decisions made for other reasons. The tech has made extraordinary strides - agentic AI in the last few weeks has been genuinely surprising, even to those watching it closely - but there is a long distance between "this technology is impressive in demonstration" and "this technology is embedded well enough to reliably substitute for significant human capital."
The organisational plumbing hasn't been laid in most companies. Review frameworks for AI-generated work don't exist at scale. The cognitive load of working at faster pace with agentic outputs is largely unanswered.
What I'd call the actual transformation work: the change management, the process redesign, the cultural scaffolding that makes AI augmentation function well rather than become a source of invisible operational risk. This work simply hasn't happened in most organisations. It takes careful effort, not a quarter's notice period.
Dorsey may be right about Block - he knows his business. What worries me is the signal that 22% sends to every CEO watching. The incentive for rapid headcount reduction has just been made very explicit, and the market has shown it will reward the announcement regardless of whether the underlying work has been done.
The tipping point in technology transitions isn't always when the technology is ready. It's when the perceived cost of waiting outweighs the perceived risk of moving. We may have just watched that moment arrive for AI-driven workforce decisions, ahead of the infrastructure that would make those decisions sensible.
The question I keep returning to is whether we're watching the beginning of a well-managed transition, or the opening act of a period where a lot of organisations make the same expensive mistake in rapid succession: cutting before the foundations are in place, then discovering what they've lost when it's too late to recover it.
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