The $400K Chief of Staff moment is real. Navigating it is the hard part. ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌

Hey {{first_name|there}},

Bloomberg just called the Chief of Staff the CEO's secret weapon in the AI age. The moment is real. What you do with it is the harder question, and that's what this week is about.

This week:

  • New on the blog: when to stay, when to grow in place, and when to go
  • Chief of Staff Connect returns to New York, October 22 and 23
  • Events in Dallas, Mumbai, Riyadh, and more

Scroll on!

Scott

 

When to Stay, When to Grow, When to Go

Career Progression for a Chief of Staff

Bloomberg ran a piece last week on the $400,000 Chief of Staff, and 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. The role 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, from carrying the bag to cracking open new markets. That variance is where careers in this role get decided. The real question isn't your next title. It's whether you're closing the distance to the strategic version of the role, and whether your current seat is helping. Our new post breaks the decision into three calls, stay, grow in place, or go, with the tells for each.

Read the post

👉 Read the post

🤝 Chief of Staff Connect returns to New York

On October 22 and 23, Connect comes back to New York for two days with senior Chiefs of Staff building the next generation of company execution. This year's theme is From Force Multiplier to Builder: the shift from amplifying leaders behind the scenes to owning the systems, programs, and operating models that move the business forward.

Expect sessions on architecting operating systems that scale, shipping projects that move metrics, and stepping into the Chief AI Architect seat. If you're driving strategic initiatives or leading transformation, this is your peer group, in the middle of Manhattan.

Chief of Staff Connect - New York, October 22-23, 2026
Join us

October 22-23 in New York. Bundle your ticket with PRO+ membership and save up to 24%.

 

Upcoming Events

📍 Next Week

JUL
28
TUE
Dallas Chief of Staff Meetup
Dallas In Person

Chief of Staff chapter meetup in Plano. Next Tuesday evening.

Next 2 Weeks

JUL
30
THU
CoS AI Buildathon, Part 1: Your First Two Skills
Virtual

Hands-on build session: start your personal AI workspace with your first two skills.

JUL
31
FRI
Mumbai Chief of Staff Network Chapter Launch
Mumbai In Person

Official launch of the Mumbai Chief of Staff chapter. New city, new community.

AUG
2
SUN
Riyadh Chief of Staff Chapter Launch
Riyadh In Person

Official launch of the Riyadh Chief of Staff chapter.

August & September

AUG
27
THU
CoS AI Buildathon, Part 2: From Skills to Connected Projects
Virtual

Part 2 of the Buildathon: connect your skills into working projects.

SEP
9
WED
Austin Chief of Staff Meetup: AI Demo Night
Austin In Person

AI demo night with the Austin chapter: members show what they've actually built.

SEP
10
THU
Frankfurt Chief of Staff Chapter Launch
Frankfurt In Person

Official launch of the Frankfurt Chief of Staff chapter.

SEP
14
MON
Chief of Staff Connect - Berlin Forum
Berlin In Person

Connect Forum in Berlin. A high-level gathering for senior practitioners.

SEP
15
TUE
Chief of Staff Launchpad: September Cohort
Virtual

Cohort program for new and rising Chiefs of Staff. Applications open now.

SEP
16
WED
Boston CoS Meetup
Boston In Person

Chief of Staff chapter meetup in Boston.

SEP
24
THU
CoS AI Buildathon, Part 3: The Dashboard
Virtual

Part 3 of the Buildathon: bring your workspace together in one dashboard.

See you next week,

Scott

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