Chicago Chief of Staff Meetup (Thu Jun 25)
We’re excited to bring the Chief of Staff Network (COSN) community back together in Chicago for our next gathering this June.
Following a strong start to the year and a fantastic turnout at our last event, we’re continuing to build momentum and deepen connections within the Chicago CoS community.
A special thank you to Jen Kaufmann for hosting and continuing to grow the Chief of Staff community in Chicago.
Date & Time: Wednesday, June 25, 2026 · 6:00 PM CT
Location: Arlington Heights, IL (shared upon confirmation of attendance)
For this meetup, we’re trying something a little different.
While still keeping the event informal and welcoming, this session will have a slightly more “business-focused” feel, with a light show-and-tell component built into the evening.
A few attendees will share practical examples from their work, offering a behind-the-scenes look at how they approach challenges, build systems, and support their leadership teams.
Think of it as a chance to move beyond surface-level networking and into more tactical, real-world insights from fellow Chiefs of Staff.
What to expect
A casual but slightly more structured gathering
Short, practical “show & tell” moments from peers
Meaningful conversations with fellow Chiefs of Staff and operators
Wine, light bites, 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 connecting with peers and learning how others are solving real operational challenges, we’d love to have you join us.
Attendance will be capped to keep the group intimate and high-quality — 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/