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[Webinar] Being A Chief of Staff In 2026: What’s Changed, What Hasn’t, What Matters Now
Over the past 12–18 months, we’ve seen something shift…
Every fast-growing company seems to be hiring a Chief of Staff.
But ask five companies what that role actually does, and you’ll get five completely different answers.
Some Chiefs of Staff are running exec offsites and driving alignment.
Others are acting as extensions of the CEO.
Some are deep in operations… others are shaping company strategy.
And most are figuring it out in real time.
So what does “great” actually look like in 2026?
We’re bringing together a group of operators who have seen the role from every angle:
Clara Ma, Founder of Ask a Chief of Staff
Scott Amenta, Founder of the Chief of Staff Network
Casey Boyles, Chief of Staff to the COO at Guild
Jared Kleinert, Founder & CEO of Offsite (moderator)
In this live session, we’ll break down what’s really happening inside the Chief of Staff role right now… what’s working, what’s not, and where it’s all heading.
Here’s what we’ll cover:
How the Chief of Staff role has evolved heading into 2026
What high-performing Chiefs of Staff are actually spending their time on (vs. what they think they should be doing)
The biggest challenges Chiefs of Staff are facing right now… and how they’re navigating them
How the role changes across company stage, leadership style, and org structure
Where Chiefs of Staff are driving the most impact today (hint: it’s not just meetings and notes)
We’ll also spend time on something that’s becoming increasingly important:
How Chiefs of Staff are owning offsites, executive alignment, and company-wide planning… and what separates a high-impact offsite from a wasted one.
This won’t be a generic panel.
It’s a candid, behind-the-scenes conversation with people actually in the role… sharing what they’re seeing across dozens of companies.
If you’re a Chief of Staff, work closely with one, or are thinking about hiring one… this is worth your time.
Save your spot now!