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Bloomberg ran a piece last week with a headline every operator should sit up for: the $400,000 Chief of Staff is the CEO's secret weapon in the AI age. The numbers behind it are real. Postings for the role more than doubled last year. The count of people holding the title in North America has more than tripled since 2021, concentrated in tech and financial services. As the CEO job gets more complex and the AI age piles uncertainty and change management on top of it, more leaders are reaching for the same human answer: someone beside them who can think, decide, and carry the hard things.
That's the good news, and it's worth sitting in for a second. The role you're in, or trying to get into, is having the best moment it has ever had.
But read that same article closely and you notice the catch. The role it describes is all over the map. One minute the Chief of Staff is taking notes and drafting a speech, the next they're cracking open a new market or reading the temperature of a factory floor. One source compares it to a caddy who is sometimes a real partner deep in the strategy and sometimes just there to carry the bag. The people in these seats arrive from everywhere: executive assistants, project managers, strategy consultants, some early in their careers, some much later. Same title on the business card, wildly different jobs underneath.
That variance is where careers in this role get decided.
The role isn't undefined. The gap is.
It's tempting to read all that range and conclude the job simply has no definition. That's not exactly right, but it matters that we get it right. The senior, strategic version of this role has a very clear shape. It's the person who amplifies the CEO's thinking rather than just relaying it, who owns the projects that actually move the business, and who can tell the boss what she doesn't want to hear. As one former Chief of Staff told Bloomberg, you have to be able to say what you really think, and it won't always be welcome. That version is real, it's increasingly well understood, and it's what the best people in this role are already doing.
What's ambiguous is everything below that line. And that ambiguity isn't a flaw in the role. It's the room you get to grow into. Because the earlier rungs aren't rigidly defined, scope can stretch, and it stretches in two directions. Sometimes the Principal's needs pull you upward, handing you bigger problems because there's no one else positioned to take them. Sometimes you take the ground yourself, deliberately, before anyone hands it to you. Either way, the distance between where most people in the title sit today and that senior version is not a wall. It's a gap worth closing.
The real career question for a Chief of Staff isn't "what's my next title." The title is booming and it still tells you almost nothing. The question is whether you're closing the distance to that strategic version of the role, and whether your current seat is helping. Most of the hard calls sort into three: stay, grow in place, or go.
Stay
Stay while the seat is still pulling you toward the strategic version, even if the title and the pay haven't caught up. Early in a strong run, the growth often outpaces the comp. You're hearing problems a level above your formal scope, you're in rooms you technically have no business being in, and the CEO is starting to test decisions on you before taking them anywhere else. That access is what enables you to grow, and it's worth more for a while than a bigger number somewhere else.
The tell that staying is right: you end most quarters slightly out of your depth in a useful way, the mandate expanding faster than you can fully master it. When that's true, leaving for a cleaner title usually means rebuilding trust from zero, and trust is the currency this role runs on.
Grow in place
The most underused move in this role is widening the seat without leaving it, and the ambiguity we just named is exactly what makes it possible. Because the shape of the job below the senior line is loosely drawn, you often have more room to redraw it than people in rigid roles do. Growing in place means deliberately trading execution you've already mastered for judgment work. It's handing off the report you could build blindfolded to a system or a hire, and using the space that opens to move upstream into the decisions themselves.
Bloomberg's own sources point at where the opening is right now: as executives race to adopt AI, the Chiefs of Staff gaining the most stature are the ones building the new workflows, dashboards, and accountability systems the org suddenly needs. That only counts as progression if the time you free up gets reinvested in strategy and judgment. Automate your way to more capacity and then absorb more execution, and you've just made yourself a faster version of where you already were. The build is the means. The strategic seat is the point.
The best Chiefs of Staff are moving from force multipliers to builders.
A force multiplier makes one leader more effective. A builder makes the whole business run better, and puts up the systems, operating cadence, and AI workflows that keep working after they leave the room. That shift, from amplifying someone else's work to owning the machine that produces it, is exactly how you close the distance to the strategic seat.
CoS Connect is where those builders are in one room. Come find the people already operating at the level you're building toward.
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Go
Go when the ceiling is structural, not personal. There's a version of feeling stuck that's really just a hard stretch of the same job, and leaving in the middle of that is a mistake. There's another version where the limit is built into the situation: the Principal only ever wants a note-taker and will never want a thought partner, the company treats the role as a two-year rotation on the way to somewhere else (the median tenure sits around 2.3 years for a reason), or the strategic work is permanently owned by people who will never cede an inch of it. In some cases, the company or Principal never really needed a Chief of Staff in the first place.
No amount of good work on your part moves that. The signal is when your growth has clearly outrun the seat's ceiling and the ceiling isn't moving. You're the most capable you've ever been and the least challenged, and every pitch for a bigger mandate comes back as a polite no about the shape of the role rather than about you. Take the trust and the track record you've built and go find a seat with actual room in it.
Demand isn't the same as arrival
Here's what the boom obscures. The market is minting the title far faster than it's minting the senior operator behind it. Two-thirds of people who come out of the role go on to bigger jobs, and the roster of Chiefs of Staff who became COOs and founders is long and still growing. But that upside belongs to the people who actually closed the gap, not to everyone who simply held the title. The demand is real. The definition at the top is real. The distance in between is where the work is.
That distance is exactly what we exist to close. Chief of Staff Network is the on-ramp: the community, craft, systems, and career support that take you from holding the title to operating as the strategic partner the role is becoming. The secret weapon the CEO is looking for isn't the title. It's the person who grew into it.
Three podcast episodes worth listening to
If this is the question you're sitting with, three conversations from The Chief of Staff Podcast go deeper on it:
- CoS to Functional Leader (and Back): Judy Abad's Career Playbook — Judy has moved between Chief of Staff and functional leadership at Facebook, Slack, WhatsApp, and Freshworks, and makes the case that P&L and team size are proxies for seniority, not the real thing. The clearest listen on why the seat matters more than the label, and how to know when to walk away from a losing hand.
- Escaping the Doer Trap with David Kirby — The former Ford Chief of Staff on why the execution skills that win you the seat are the same ones that trap you in it, and what moving from doing to orchestration actually takes. This is the gap, named, with a playbook for closing it.
- The Career Accelerant: Lessons from a Chief of Staff Turned COO — Bryan Silverman discusses his career path from CoS to COO at Suzy, the glass ceiling many Chiefs of Staff face around P&L ownership and people management, and how AI is shifting the balance from execution to problem selection.
