The morning after the fire
The great restructuring and the ground zero of marketing
On Thursday evening, Jack Dorsey published a letter to Block’s shareholders. In it, he announced that 4,000 people (nearly half the company’s entire workforce) would be let go.
Not because the business was struggling. Gross profit was up 24% year-over-year. Cash App is growing. Square is humming.
He did it because he believes intelligence tools (aka AI) have made those jobs unnecessary.
And then he said the part that matters:
“Within the next year, I believe the majority of companies will reach the same conclusion and make similar structural changes.”
Jack Dorsey
The stock jumped 24% overnight. NASDAQ followed with tech stocks jumping up. The market seems happier than ever. Unreal.
Not a gradual restructuring. Not a month-by-month layoff spiral. But a brutal amputation overnight. In any other case, the market would frame it as a proof of failure. Not now, not here, not for the others coming.
The canary died in the coalmine.
We cover the most important AI developments for marketers. One thing you need to know about AI on this day, as we say. The reason why we write about this news is a simple one: we believe this is the most important AI-related news this week. Probably this month. I might argue this year so far.
If you are employed, you should read this.
I want to be very precise about what I think is happening, because there is a version of this essay that descends into fear-mongering, and that is not what this is.
I’ve spent every working day for the past year studying how AI reshapes marketing organizations. I talk to CMOs and marketing leaders weekly. I see what’s actually happening inside companies, not what the headlines say.
What I see is this: most executives don’t understand what’s coming. Not really. They feel it. A vague sense that something fundamental has shifted, that the tools their teams are experimenting with are more capable than anyone expected, that the old organizational math doesn’t quite add up anymore. But they can’t articulate it. They don’t know which workflows to cut, which roles to restructure, which teams to merge. They’re frozen in a gap between intuition and action.
This is actually the more dangerous scenario.
Because the tools aren’t waiting for executives to catch up.
Every month, AI gets measurably better at the exact tasks that fill corporate calendars and payrolls. Content production. Data analysis. Campaign optimization. Reporting. Research. Coordination. What AI can do and what companies are still paying humans to do are converging fast. And the cost difference is becoming impossible to ignore.
Right now, figuring out how to restructure around AI requires genuine strategic thinking. You need to map workflows, understand tooling, and redesign processes. It takes vision.
Within a year or less, it won’t require vision at all.
The tools will be so obviously capable, so simple to deploy, so clearly cheaper than the alternative, that the decision will make itself. You won’t need to be a visionary CEO to see it. You’ll just need to read a cost comparison on a single slide.
That’s the shift. We’re moving from a period where only the Dorseys of the world — the ones who think about this obsessively, who build internal AI tools, who have the conviction to act on incomplete information — will restructure. Into a period where every CFO in every quarterly review will look at the numbers and say: Why are we still paying for this?
And by this, I mean humans.
The executives who are clueless today won’t be clueless for long. Not because they’ll suddenly develop AI expertise, but because the technology will dumb the decision down to a level where expertise is no longer required to make it.
And when that happens, the restructuring won’t come from one Jack Dorsey. It will come from everywhere, all at once. Overnight.
What happens now
Let me walk you through what I believe is about to unfold, and then let me tell you what to do about it.
First, the restructuring wave. Dorsey isn’t an outlier. He’s just an early mover. The data has been piling up all year. In the first two months of 2026 alone, over 49,000 tech workers have lost their jobs. That’s 850 people per day.
I’m not linking the articles for proof, so you won’t click away, but some examples:
Pinterest cited AI in January when it cut 15% of its workforce.
CrowdStrike’s CEO said AI was “reshaping every industry” as he eliminated 500 positions.
Dow cut 4,500 jobs, pointing to AI and automation.
Salesforce reduced its customer support headcount by the thousands using AI agents.
Amazon cut 14,000 corporate roles.
Nestlé announced 16,000 cuts, with their new CEO writing on LinkedIn: “We will simplify our organization and automate our processes.”
I can go on and on.
But here’s what’s different about the Block announcement. Those other companies were doing 5%, 10%, maybe 15% cuts. Dorsey cut 40%. Insane. And he framed it not as cost reduction, but as the new operating model. Smaller teams. Flatter structures. AI orchestrating workflows that used to require layers of human coordination.
That is a structural argument, not a cyclical one.
When a CEO says, “We had 10,000 people, and now we need 6,000 to do the same work better,” the question every other CEO in the world is now asking themselves is not “should we do this?” It’s “how long can we afford to wait?”
The workflows that are already dead
Let me be honest about something that most people in corporate marketing know but rarely say out loud: a staggering amount of what we do every day is not work.
It’s the scaffolding around work. It’s the meetings about the meetings. The status updates about the status updates. The alignment sessions that produce no alignment. The Jira tickets that describe tasks an AI could complete in the time it takes to fill out the ticket.
I worked most of my career at startups and growing companies. Let me be frank here. We didn’t have time for the bullshit. Every time I took the helm of a leadership role somewhere, my very first decision was always the same: cut the meetings by 80% and oversimplify the workflows. We never had a meeting about how we should work around a problem, or how we should work together, and for sure, we never had any alignment or culture-centric meetings.
Those are for companies that grow 1-3% year-over-year. Enterprises. Whales. Slowmovers. With thousands of people on payroll. A minimum of 20% of them are doing nothing, just managing between the 80%. On a bad day, I would argue the %s are inverted anyway.
You know what I’m talking about… The rituals. You might live them. Let me name a few:
The Monday morning standup, where eight people spend 45 minutes going around the room saying what they plan to do this week, which everyone could have read in a Slack message in 90 seconds.
The bi-weekly sprint review, where the content team presents what they shipped to the marketing leadership team, who already saw it because it went live two weeks ago.
The quarterly business review deck, which takes three people two weeks to build, synthesizing data that an AI can pull, format, and analyze in four minutes.
The campaign brief, that travels through four rounds of feedback from six stakeholders over nine business days, where the core idea doesn’t change, but the font in the presentation does.
The weekly analytics report where someone pulls data from four platforms, pastes it into a Google Sheet, creates three charts, writes two paragraphs of analysis, and sends it to people who glance at it for thirty seconds.
I’m in a good mood, so I’m gonna stop here, but you know I could go on forever with these examples. If you count the hours in any given week and it turns out 80% of your working hours are about these examples, well… We both know what that means.
Most of these were solutions designed for an era when producing, synthesizing, and distributing information was expensive and slow. That era is over.
We knew it would end years ago. It ended months ago for sure. Most businesses will soon realize it has ended. Yes, even the dumbest, most visionless ones will know. No escape route here.
The ground zero of the fire: marketing
Now here’s where I need to be honest with you, and where I part ways with both the optimists and the pessimists.
The optimists are probably right in the long run. The World Economic Forum projects 92 million jobs displaced by 2030, but 170 million new ones created. History supports the pattern. The ATM didn’t kill bank tellers. The internet didn’t eliminate retail.
I believe new jobs will be created. I believe new roles and entire industries will emerge from this transformation.
But there is a middle. Between the old jobs disappearing and the new jobs arriving, there is a gap. And that gap is going to be brutal for people who aren’t prepared.