Chicago Chief of Staff Meetup (Wed Apr 22)
We’re excited to bring the Chief of Staff Network (COSN) community together in Chicago for our first meetup of 2026.
As we head into Q2, this gathering is focused on bringing together Chiefs of Staff and senior operators across Chicago to build stronger local connections and continue growing a high-trust community in the city.
A special thank you to Jen Kaufmann for generously hosting and helping bring the Chicago CoS community together.
Date & Time: Wednesday, April 22, 2026 · 6:00 PM – 9:00 PM CT
Location: Shared upon confirmation
This informal, in-person meetup will bring together Chiefs of Staff and adjacent operators for relaxed conversation, meaningful connections, and candid discussion about the realities of operating in strategic leadership roles.
There’s no formal agenda — just a brief touchpoint on COSN and what’s ahead for the Chicago chapter, followed by open networking and shared conversations with peers navigating similar challenges and opportunities.
Whether you’re looking to exchange ideas, learn from others, or simply meet fellow Chiefs of Staff in the area, this is a great opportunity to plug into the local community.
What to expect
A casual, welcoming environment
Meaningful conversations with fellow Chiefs of Staff and operators
Opportunities to share experiences and insights
Food, drinks, and new connections
Who is this event for?
This meetup is for operators currently serving as Chiefs of Staff, Founders’ Associates, or in similar BizOps, strategy, or operations roles.
Please include your current job title and company so we can verify your role and approve your registration.
If you’re interested in helping shape the Chief of Staff community in Chicago this year, we’d love to have you join us.
Attendance will be capped to keep the group intimate — please RSVP to save your spot.
For more information about the Chief of Staff Network and our upcoming events, programs, conferences, and more, visit:
https://www.chiefofstaff.network/