The $400,000 Chief of Staff Is CEO’s Secret Weapon in the AI Age   artwork

The $400,000 Chief of Staff Is CEO’s Secret Weapon in the AI Age  

Bloomberg Businessweek

July 27, 2026

The people, companies and trends shaping the global economy. Watch Carol and Tim LIVE every day on YouTube: http://bit.ly/3vTiACF. A growing number of corporate leaders, buckling under the stress and uncertainty of the AI age, are looking for a very human solution: A chief of staff.
Speakers: Carol Massar, Tim Stenovec, Matthew Boyle
**SPEAKER_1** (0:02)
Bloomberg Audio Studios, podcasts, radio, news.

**SPEAKER_2** (0:07)
You're listening to Bloomberg Businessweek with Carol Massar and Tim Stenovec on Bloomberg Radio.

**Carol Massar** (0:14)
We have a great story we want to get to. We've been talking about this a lot. We haven't, it's been on the terminal. We've been like, we got to get to Matt Boyle and talk about it. It has a growing number of corporate leaders buckling under the stress and uncertainty of the AI age. I would argue that's why they get paid millions, are looking for a very human solution, and that is a chief of staff.

**Tim Stenovec** (0:32)
If you want to know how hard it is to be a CEO right now, you can check out another one of Matt's recent stories as well. This one though is about a chief of staff. Matt Boyle, Senior Reporter, Work and Management for Bloomberg News. He joins us here on the Bloomberg Interactive Broker Studio.
What the heck does a chief of staff do?

**Matthew Boyle** (0:49)
Kind of everything, I would say. Yes, it is one of the most unique roles I've ever looked at in sort of the C-suite, and I guess it is in the C-suite. They're attached to the hip, to the CEO, or the division president, whoever they're working for. But let's say a CEO, you have to be a concierge. You have to be a confidant. You have to be a consigliere. You have to be kind of everything, but it all comes down to another C-word, chemistry. If you do not get along with the boss, the CEO, it's never gonna work no matter how talented you are.

**Tim Stenovec** (1:18)
Who are the types of people who are successful chiefs of staff?

**Matthew Boyle** (1:24)
Imagine you combine the best executive assistant of all time with a strategic genius from McKinsey, and you might get a great chief of staff, because one day they're just sort of answering emails or they're writing a speech for the boss. The next day, the CEO is like, oh, we got to enter the Chinese market, go figure it out, or there's a problem on the factory floor. Go take the pulse of all our factory workers and report back to me. So they are thrown on to these complex assignments with literally usually no notice, and they just kind of have to figure it out.

**Carol Massar** (1:57)
How often does a chief of staff grow along with an executive who ultimately becomes CEO, and the CEO takes them along as they move along?

**Matthew Boyle** (2:03)
Well, yeah, I spoke to one woman who did the job for both Jeff Bezos and Eric Schmidt. So if you get a taste for it, and you're in certain circles like tech, and the word gets out that you are a very good chief of staff, you can do it for some time, although the median tenure is only 2.3 years, because a lot of times they might burn out, there's no chemistry with the CEO.

**Carol Massar** (2:24)
You're also at their beck and call.

**Matthew Boyle** (2:26)
Exactly. It is a 24-7 job. Your time is not your own. I have been friends with some chiefs of staff, and we've been out for drinks at 11 o'clock at night, and there's a call coming in, got to go, my boss. So yeah, it is a tough role, but it's done by highly ambitious people who want to use that job as a springboard to something even bigger.

**Carol Massar** (2:45)
Where do they go?

**Matthew Boyle** (2:46)
They often go into the C-suite proper. It's because they are roaming around the company, they know all the inner workings, the next job can be often the chief operating officer, certainly, or you're running a business unit, a unit of the company you are at. Sometimes you just become a chief of staff again, but the real ideal is to leverage that into a C-suite role.

**Carol Massar** (3:07)
Or men or women better chief of staff? Sorry, Tim, I'm just curious.

**Matthew Boyle** (3:11)
Loaded question, yes. I don't know if it came up at all. I wish I had some stats on it, although there's a lot of statistics out there. There's a whole chief of staff association. There are executive recruiters who just hire for this role. So I never got any sort of real, like sort of hard like gender breakdown on it. But it's less, I think, to do with demographics and just more to do with how competent are you?
How much are you able to sort of put your ego aside? Because these are all ambitious people who probably want to be CEO one day. But if you are the chief of staff, it is not about you.

5 more minutes of transcript below

Feed this to your agent

Try it now — copy, paste, done:

curl -H "x-api-key: pt_demo" \
  https://spoken.md/transcripts/1000651996090

Works with Claude, ChatGPT, Cursor, and any agent that makes HTTP calls.

From $0.10 per transcript. No subscription. Credits never expire.

Using your own key:

curl -H "x-api-key: YOUR_KEY" \
  https://spoken.md/transcripts/1000778538349