Player-Executives
How AI is squeezing the corporate pyramid and handing execs the keyboard again
Manager “Span of Control” used to mean three or four direct reports and an army of skip levels, but that is changing fast. Payroll provider Gusto now says the average supervisor in a U.S. small business is overseeing almost six people, roughly double the 2019 ratio. Axios has already tagged the trend “The Great Flattening.”
This flattening trend isn’t just within SMBs. Big Tech is pushing hard in the same direction. Microsoft, Amazon, Google and Meta have each run multi‑round layoff cycles aimed squarely at middle layers. The internal memo logic is always the same: fewer handoffs, more velocity, and a tighter focus on AI investments.
What happens after this first wave of obvious cutting? My take: A new middle will form and then it will become the target of the same optimizations until eventually the org chart morphs into something new entirely.
Cost cutting or competitive edge?
The easy narrative says flattening saves money. That is true, but it is not the whole story. Mark Zuckerberg has continuously argued that “flatter is faster” since he seemingly snapped back into “founder mode” in 2022. Meta’s stock has risen 700% since.
Speed is more important to winning than cost cutting and it’s also helpful for wooing scarce talent. AI researchers, as an example, are commanding professional athlete level salaries. What else could they want? The org chart is becoming part of the employer pitch: join us and you ship, you do not shepherd.
Gartner’s 20 / 50 warning
Gartner agrees with me that the razor is only halfway through the pyramid. The firm projects that by 2026 one in five companies will have eliminated more than half of their middle‑management roles through AI‑enabled automation.
Corporate governance will stay with humans due to fiduciary concerns, but tasks like coaching and compliance are soaking up AI leverage quickly. It’s feasible that eventually the only layer left in some parts of the org chart or operationally workflows will be the executive signing off on AI deliverables.
Enter the player executive
We used to celebrate the “player coach” who could lead a team and still get hands dirty. As AI agents handle more of the glue work like status decks, calendar triage, and performance dashboards, the person at the top will be able to keep up with vision and pick up the keyboard again. A CEO who prototypes a feature at midnight is no longer a vanity story; it is an emerging operating model.
Where these shifts are happening first in the org chart
Marketing and sales: Automation can enable CROs and CMOs to generate pipeline and close deals with a skeleton crew.
Engineering and product: Code‑writing copilots mean the Head of Engineering can review pull requests on Tuesday morning and work on strategy that afternoon.
Finance: Virtual‑CFO platforms now do forecasts, flag anomalies and draft board slides so that the human CFOs can stay in strategy mode or maybe even take on more work traditionally owned by the COO. Or will it be the COO who takes on the CFOs prior work?
Super agency and blurred lines
McKinsey calls 2025 the dawn of “super agency,” where a single professional can plan, decide and act at scale with off‑the‑shelf AI agents. Many VCs are waxing poetic about the potential for a “$1 billion dollar single person startup”.
If every individual contributor and executives have access to the same AI superpowers, what exactly differentiates an executive from a high performing IC and why wouldn’t they end up competing with one another in the open market?
My current answer: executives still have better capital access, more risk appetite, more experience, and the moral authority that is required to convince others to follow their vision… but my conviction about this is low.
Agents as synthetic middle managers
Lists of “Top AI agents” read like a Who’s Who of jobs that used to belong to coordinators and junior PMs. Tredence’s recent roundup includes bots that escalate tickets, draft contracts and run sprints without a human in sight.
My take is that hiring agents onto your team will look less like HR-led hiring processes and more like procurement—choose your agent, set the permissions, swipe your corporate card.
The (temporary) oversight bottleneck
A 2025 arXiv model argues that high hallucination risk can actually increase demand for human validators, at least temporarily narrowing spans of control again.
My bet is that firms will iterate their way past that bottleneck, but I expect an awkward middle phase where human QA becomes the new traffic jam while org charts evolve. The most visceral version of this today is a senior engineering leader spending hours telling their coding agents, “Nope. It’s still broken. Look into XYZ.”
Culture and the apprentice void
Cutting the middle layer removes more than status reports; it erases a key conduit for organizational knowledge and a development pipeline for future executives. Korn Ferry’s 2025 workforce survey found that 37 percent of employees in flattened companies feel directionless. We need to figure out how to make sure that our current leaders + AI don’t “pull up the ladders” on the next generation.
Some companies, like Box, offset the gap with “eat what you kill” incentives that let executives reinvest any resources they save, giving them skin in the game that they could theoretically re-invest into mentorship or other continuity planning.
Whether that is enough is an open question.
No spare heads when AI misfires
Lawmakers are already sharpening knives to go after executives who employ AI in ways they don’t approve of. Three U.S. senators just grilled Delta about AI‑driven ticket pricing that might push fares to each traveler’s pain point. Corporate accountability stays at the top even when an algorithm writes the logic.
When you choose the player‑executive route, you also volunteer to be the last name on the accountability slide.
Player executives in early-stage startups
Just like always, early‑stage startups are offering us a live look into the future that more corporations will likely evolve into. Andreas Just has a great piece outlining some of these AI startup trends. He uses Lovable as an example of companies that are scaling revenue quickly, but with very small teams.
They are not just lean. They are building org charts that never create rungs to remove in the first place.
Looking Ahead: The Skills, the Questions, and a Real‑World Example
Whether the “player executives” future really comes to be across all industries and company sizes, executives who wants to stay relevant in a flatter, agent‑filled world will need a fresh kit of hands‑on abilities and they will need to shake off any fear they have of picking up the keyboard again.
My take: You will not learn any of this by debating case studies in an MBA seminar.
The only reliable classroom is being in the water. You need to spend your time shipping real work with real tools and real teams, making real mistakes, and iterating as you go.
A good real-world example of this is my friend Tom Burke.
After running growth teams at Uber, SoFi, and OpenSea—and earning an MBA from NYU—Tom could have easily landed another pyramid‑top job. Instead he joined OpenAI, picked up the keyboard again, and began operating as what I’d consider a player executive (though he may not use the same language). He was a big inspiration for this post and I bet he is learning faster than any syllabus or pyramid-top job could ever offer him.
Before you declare bankruptcy on your own org chart, sit with three questions:
Which workflows in your company could agents absorb soon and how can you test them out?
If a ten‑fold AI productivity boost arrived tomorrow in your current role, what part of the job would the company refuse to delegate to AI because of governance, compliance, ethics, or some other reason? Assume the rest are going to AI or someone else in the org.
When the ladder loses a few rungs, how will you still make sure rookies at your company have a way to grow into future executives?
If you’re in this player executive transition now, I am collecting examples for a follow‑up piece: “Tales from the first wave of player executives.”
If you are already living this future, I want to hear how it feels!
Thanks for reading. If this sparked an idea—or a panic attack—share it with a colleague who still has two managers above them. They may not for long.