The New $1M Salary Band

Three CEOs. Three companies. Three different industries. Same decision. Same 90 days.

Jack Dorsey cut more than 50% of Block's workforce. The day he announced it, the stock went up. Zeb Evans cut 22% of ClickUp and announced salary bands up to $1 million for the people who stayed. Ryan Breslow fired Bolt's entire HR department — he'd seen this coming nearly a year before anyone else did.

This isn't a trend. It's a structural reset. And the market is applauding every move.

Three CEOs, One Message

Let's start with the numbers, because they're hard to argue with.

Jack Dorsey, founder of Twitter and CEO of Block, cut more than half his company in February 2026. Not because Block was failing. The company runs a global financial platform — Cash App, Square, and a growing bitcoin infrastructure business. Dorsey's reasoning, delivered in a note to employees: "Smaller and smarter teams can achieve outcomes that previously required hundreds of personnel."

The market response? Block's stock went up the day he announced it. Investors didn't punish him. They rewarded him. Because the people reading those filings understood what most professionals inside corporate America are still trying to process: AI has fundamentally changed the math on headcount.

Zeb Evans, CEO of ClickUp, made a similar call in May 2026. He cut 22% of his workforce — roughly 280 people — from a $4 billion company with $300 million in annual revenue. Not a company in distress. A company making a deliberate architectural decision.

Evans is running 3,000 AI agents inside ClickUp. Against roughly 1,000 employees, that's a 3-to-1 ratio of agents to humans. He said the quiet part out loud: the people who couldn't direct those agents were, in his words, expensive overhead. Then he announced salary bands up to $1 million for the people who could. He calls it the 100x org.

Ryan Breslow, CEO of Bolt, had already seen this coming. Nearly a year before the current wave hit, he eliminated Bolt's entire HR department and posted about it publicly on LinkedIn. His framing: "More focused on efficiency, less focused on fluff." In 2026, he followed it up by cutting 30% of Bolt's workforce — down to roughly 100 employees — and sending a company-wide message: "We need to be leaner and more AI-centric than ever to keep up with competition."

Three CEOs. FinTech, project management software, payments infrastructure. Three separate decisions that arrived at the same conclusion.

The Shift Evans Described In One Sentence

Of all the things said publicly about this transition, one quote from Zeb Evans captures it more precisely than anything else I've read:

"The biggest shift is from actually doing and waiting on the work, to reviewing the work and ensuring that it meets your standards."

Read that carefully. From doing and waiting — to reviewing and directing.

That one sentence is the new job description for every senior professional in this market. It's not about working harder or learning a new tool. It's about a fundamental change in where your value sits in the workflow.

For most of the last 30 years, the professional who executed the process well was the valuable one. The person who ran the analysis, drafted the report, managed the checklist, processed the request. Speed and accuracy at task execution was the currency.

What Evans is describing is a world where AI executes those tasks. Faster, cheaper, without vacation days or performance reviews. And the human's job — the job worth $1 million — is to know what good looks like. To set the standard. To review the output and direct the system toward better outcomes.

That's not a small shift. That's a complete inversion of where value lives in the organization.

The Fear Is Real — And It's Appropriate

Let me be direct about something, because I think a lot of commentary around AI softens this in a way that doesn't serve anyone.

If your job is primarily task execution — running the same reports, processing the same requests, managing the same compliance checklists — that work is going away. Not eventually. It's going away now. The three CEOs above didn't make these cuts as a future projection. They made them because the tools that replace that work are already deployed and running.

Breslow didn't say HR would eventually be disrupted. He said the problems his HR team was creating disappeared when he let them go. That's not a projection. That's a post-mortem.

Dorsey didn't say AI would eventually reduce headcount. He said AI-assisted coding, compliance systems, and automated customer support had "significantly reduced the man-hours required to run a global financial platform." Past tense.

Evans isn't running 3,000 AI agents as a pilot program. They're live, operating at a 3-to-1 ratio to his human workforce, producing work that used to require a much larger team.

The fear that task-dependent professionals feel right now is not irrational. It's accurate pattern recognition. The market is telling you something. Three CEOs just put it in writing.

The Unlimited Side of the Equation

Here's where the conversation changes.

Evans didn't just announce layoffs. He announced that the $1 million salary band is available to nearly anyone in the company who produces 100x impact by creating or managing AI systems. Not the C-suite. Not just engineers. Anyone.

Think about what that means structurally. One professional, with 20 years of domain expertise, directing AI to produce outcomes. What's the ceiling on that output?

There isn't one.

If you spent 20 years in enterprise sales, you know how deals move through Fortune 500 procurement. You know the CIO who signs the contract, the legal team that redlines it, the procurement officer who can stall it for six months. AI doesn't know that. AI can draft the email, build the proposal, run the analysis — but it cannot replicate the judgment you've built across hundreds of enterprise relationships.

When you combine that judgment with AI tools that execute at machine speed, you're not just more productive. You're producing outcomes that a full team couldn't match a few years ago. And the companies being rebuilt around this model are starting to price that correctly.

Evans put a number on it: $1 million.

Dorsey described the principle: smaller teams, same or greater outcomes.

Breslow demonstrated it: 100 people, running a company that once employed hundreds more.

The W-2 professional who spent a career as a slave to his tasks just became the master of his outcomes. And the ceiling on those outcomes is whatever that person decides it is.

The Three Types Who Win This Transition

Evans publicly named three categories of workers inside his 100x org. Here's how they map to what I've been seeing in the market.

Orchestrators are the senior leaders who direct AI systems across functions and set strategic direction. They're the ones Evans describes as producing "100x impact" — not by doing more work themselves, but by building the operating architecture that multiplies the output of everyone and everything around them. Former C-suite and VP-level operators with strong cross-functional instincts are the natural fit here. They've spent careers managing complex systems. Now the system includes AI agents.

Systems Builders are the professionals who architect the AI infrastructure layer — the people who understand how to design, deploy, and manage the workflows that make the 100x org actually function. This is often a technical role, but not exclusively. Senior operations leaders, enterprise architects, and technology strategists who can translate business problems into automated systems are enormously valuable here. They're the ones building what Dorsey described as "AI-assisted coding and compliance systems" — the internal infrastructure that makes a 50% headcount reduction possible without losing output.

Domain Translators are professionals who apply deep domain expertise inside AI-native companies. The judgment, the relationships, the pattern recognition that took 20 years to build — and that AI cannot replicate. An enterprise sales leader who knows how to navigate a Fortune 500 procurement cycle. A regulatory affairs professional who understands how a compliance framework actually gets enforced versus how it reads on paper. A supply chain expert who can read a disruption signal three weeks before it becomes a crisis. These are the "front-liners" Evans described — customer-facing, judgment-dependent, irreplaceable by any model currently available.

You already fit somewhere in that picture. You may have been doing it for years without a framework to name it. The difference now is that the companies being rebuilt around this model are actively searching for these profiles — and beginning to price them the way Evans announced.

Two Paths Forward

There are two ways to position yourself in this transition, and I don't think one is obviously better than the other.

The first path: you walk into one of these companies — a ClickUp, a Block, a company at the same inflection point — as the person who can build or direct their AI operating system. The $1 million hire Evans is structuring his compensation around. You bring the domain expertise, the enterprise instincts, the leadership track record. They bring the platform and the infrastructure. You produce 100x outcomes inside one organization, and you get compensated accordingly.

The second path: you build the practice that does it for five companies at once. Instead of one employer getting 100% of your expertise, you deliver fractional access to three or four companies that each need a senior Domain Translator but can't justify — or find — a full-time hire at the level they actually need. Your output is still 100x. Your income isn't capped by one company's salary band. And you're not dependent on any single organization's decisions about headcount.

Most of the professionals I work with don't have to choose. They run both tracks simultaneously — pursuing the right W-2 opportunity while building the market presence that creates inbound interest for advisory work. The goal isn't to escape corporate. The goal is to stop being entirely dependent on it.

The window for both tracks is open right now. The restructuring wave these three CEOs represent isn't cresting — it's still building. The companies making these moves are actively looking for the people who can help them do it right. And the fractional market for senior AI-fluent domain experts is moving faster than the traditional hiring cycle can keep up with.

The Question That Matters

The question isn't whether this is happening. You just read what three CEOs said publicly, in their own words, backed by their own headcount decisions. The market confirmed every one of those moves by bidding the stocks up.

The question is which side of it you're on — and whether you know which of the three types you are.

That's the conversation I have with professionals every week. Not "should you be scared" (the answer depends on where you sit) and not "quit your job and go fractional" (that's not the right frame). The real conversation is: given what you've built over 20 years, where is your leverage highest? Which companies in which domains need exactly what you know? And how do you walk into those conversations from a position of expertise rather than desperation?

Ready to Figure Out Your Next Move?

Wishing you a happy and restful Memorial Day weekend. Take a moment to honor those who gave everything so we could have the freedom to build something of our own.