Is Chief of Staff a Dead-End Role? What 3,000 Careers Show

Guest: Tom Guthrie, Co-founder, Chief of Staff Network
Host: Scott Amenta, Founder, Chief of Staff Network

Episode Overview

The question Chiefs of Staff ask more than any other is where the role leads. The 2026 Chief of Staff Pathways report tracked nearly 3,000 careers to answer it, and the answer is more interesting than "it's a launchpad." The big jump usually comes one move later, staying put often beats leaving, and more Chiefs of Staff than ever are starting companies.

About the Report

Our first Pathways report in 2023 covered about 400 alumni from the Chief of Staff Network community. This edition covers nearly 3,000 Chiefs of Staff with dated career histories, close to 2,000 moves directly out of the role, and nearly 2,000 job postings with Chief of Staff in the title. Scott and Tom were both Chiefs of Staff in the early private-sector wave around 2016 and 2017, when nobody could say where the role went next.

Key Takeaways

• 53% of Chiefs of Staff leave more senior than they arrived, and 1 in 5 hold a VP or C-suite role within three years. That jump usually lands on the second move, not the first.

• Staying beats leaving. 61% step up when they stay versus 48% when they leave, and two to three years in the seat is the sweet spot.

• Two in three new VPs and heads of ops get there inside the company where they were Chief of Staff. Own a project, and the project becomes the next role.

• Founder exits grew from about 2% in 2020 to about 10% in 2025. Pragmatism, sound business models and lean teams are what founding takes now, and Chiefs of Staff have all three.

• 27% of job postings ask for consulting experience, but only 7% of Chiefs of Staff came from consulting. Operations is the real on-ramp.

Read the Report

The full 2026 Pathways report, with all seven pathways and real member career routes, is at www.chiefofstaff.network/blog/chief-of-staff-pathways-report-2026.