Where Chiefs of Staff Go Next: An Early Look at the 2026 Pathways Report

Hi {{first_name|there}},

For years, the question I heard most from Chiefs of Staff was some version of "is this role a dead end?" So we spent the last few months answering it properly. We followed the dated career histories of 2,869 Chiefs of Staff in our community, tracked 1,992 moves out of the role and read 1,819 Chief of Staff job postings.

The 2026 Chief of Staff Pathways Report lands in your inbox next week. You're getting an early look at what we found. Plus, Chief of Staff Connect London is just over two weeks out, and there's a full month of events from Brisbane to Montreal.

Scroll on!

📊 Where Chiefs of Staff go next

The short answer to the dead-end question is that most Chiefs of Staff leave the role more senior than they arrived. Within three years of leaving, about one in five have reached COO, VP of Operations, General Manager, Chief Strategy Officer or CEO.

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53% of Chiefs of Staff hold a more senior title after the role than before it.

2026 Chief of Staff Pathways Report

Three findings stood out to me.

The executive jump comes one step later. About 10% land at C-level on their very next move. Within three years, 16% are in the C-suite and another 13% are at VP. If you judge the role by the job right after it, you're looking too early.

Staying put works. Two thirds of Chiefs of Staff who become VP or Head of Operations do it at the company where they were Chief of Staff, and the median gap between the two roles is zero months. 61% step up when they stay, against 48% when they leave. That runs against most of the career advice I hear.

Two to three years is the sweet spot. Chiefs of Staff who stay two to three years are the most likely to step up (57%). Leave inside a year and that drops to 38%. The median stint is 20 months, which means a lot of people walk out just before the odds peak.

What's in the full report

There's a lot more coming next week, including:

The seven pathways out of the role, each with a typical route and a real, anonymized member career history
Why founding a company has grown five-fold as a share of moves since 2020
What the market pays for the role, and the one operator role that out-earns it
The consulting myth: what job postings ask for versus where Chiefs of Staff actually come from
Who Chiefs of Staff support now, and how far the role has moved beyond the CEO's office
Seven moves to make if you're planning your own next step

Keep an eye on your inbox next week for the full report.

🇬🇧 Chief of Staff Connect London, November 13

If the data has you thinking about your own next step, London is a good room to think it through. Libby Dangoor talks through the path from Chief of Staff to COO and beyond, which happens to be the most common route in the report. Farah Cohen and Dora Nagy take on why you'd need a Chief of Staff if you already have a COO, and the team from Portswigger runs a hands-on AI workshop where you leave with one of your own workflows rebuilt.

Regular Admission pricing ends this Sunday Nov. 1!

Join us in London