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Chicago

Chicago

Welcome to the Chicago Chapter of the Chief of Staff Network — bringing together operational leaders in the heart of the Midwest. Our chapter serves Chiefs of Staff across Chicago's diverse economy, from Fortune 500 headquartered companies to fast-growing startups in the Loop and beyond. Whether you're in CPG, hospitality, finance, or tech, this is your home for real talk, shared learning, and meaningful relationships with fellow CoS professionals.

Want to be a part of the CoS community?

We are an invite only community welcoming new members who meet the following criteria.

You are currently a Chief of Staff*
You work in the private sector (non-government)
You’re ready to actively participate in the community
*Your job title should include Chief of Staff in your public profile.
Join Us
Not a Chief of Staff yet? Contact Us

Chicago

Connect with senior Chiefs of Staff driving global business leadership.

Our chapters are supported by a network of top organizations across industries.

Chicago

Welcome to the Chicago Chapter of the Chief of Staff Network — bringing together operational leaders in the heart of the Midwest. Our chapter serves Chiefs of Staff across Chicago's diverse economy, from Fortune 500 headquartered companies to fast-growing startups in the Loop and beyond. Whether you're in CPG, hospitality, finance, or tech, this is your home for real talk, shared learning, and meaningful relationships with fellow CoS professionals.

Join the Community

The Chief of Staff network has been incredibly helpful for me, and I honestly started seeing immediate value on Day 1 of joining.

The network offers numerous opportunities to further growth, development, and camaraderie - I think it'd be challenging to navigate the CoS role alone without this group of people.

Ali Sardinia

Chief of Staff, Order.co

Chiefs of Staff often operate as a one-person department with limited access to peers. The Chief of Staff Network is an incredible community to find like-minded individuals to brainstorm and problem solve with.

Megan Wendholt

Chief of Staff at Gainsight

Our Chapter Leader

Jen Kaufmann
Chief of Staff, Cooper's Hawk Winery and Restaurants
Jen Kaufmann is the Chapter Lead for the Chicago Chief of Staff Network. She currently serves as Chief of Staff at Cooper's Hawk Winery and Restaurants, where she drives strategic priorities and operational excellence across a rapidly growing hospitality brand. Jen's experience in fast-paced, consumer-facing businesses gives her a practical perspective on the CoS role. She is passionate about building a Chicago chapter that brings warmth, substance, and genuine connection to every gathering.

Chapter Events

Current Events
Past Events
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Chicago Chief of Staff Meetup (Thurs Nov 6)
Nov 6

Chicago Chief of Staff Meetup (Thurs Nov 6)

Come connect with other CoS in Chicago! - When: Thurs November 6th at 6:00 - Location: Once you RSVP, you will get the location! Special thanks to Jen Kaufman for hosting this. WHO THIS EVENT IS FOR This event is primarily for in-role Chief of Staff and/or our members. You can learn more about our membership here!

Register
Chicago CoS Meetup (Thurs April 10)
Apr 10

Chicago CoS Meetup (Thurs April 10)

Come connect with other CoS in Chicago! - When: Thursday April 10th at 6:00 - Location: Once you RSVP, you will get the location! Special thanks to Jen Kaufman for hosting this where she works! Learn more about the Chief of Staff Network here!

Register
Chicago CoS Meetup (Feb 9)
Feb 9

Chicago CoS Meetup (Feb 9)

Register
Chicago CoS Summit (Nov 16)
Nov 16

Chicago CoS Summit (Nov 16)

Register
CoS Chicago HH 3/22
Mar 22

CoS Chicago HH 3/22

Register
Chicago CoS Meetup 2/8
Feb 8

Chicago CoS Meetup 2/8

Register
Chief of Staff Learning Programs
Member only

Chief of Staff Fundamentals Track

A cohort program designed specifically to jumpstart or refresh your Chief of Staff career.

Length

6 weeks

Start Date

6 weeks

Attend next cohort
Chief of Staff Learning Programs
Member only

Chief of Staff Leadership Accelerator

A cohort program designed specifically to jumpstart or refresh your Chief of Staff career.

Length

6 weeks

Start Date

6 weeks

Attend next cohort
Chief of Staff Learning Programs
Member only

Chief of Staff Leadership Accelerator

A cohort program designed specifically to jumpstart or refresh your Chief of Staff career.

Length

6 weeks

Start Date

6 weeks

Attend next cohort
Chief of Staff Learning Programs
Member only

Chief of Staff Leadership Accelerator

A cohort program designed specifically to jumpstart or refresh your Chief of Staff career.

Length

6 weeks

Start Date

6 weeks

Attend next cohort
Chief of Staff Learning Programs
Member only

Chief of Staff Leadership Accelerator

A cohort program designed specifically to jumpstart or refresh your Chief of Staff career.

Length

6 weeks

Start Date

6 weeks

Attend next cohort

Don't miss the next Chief of Staff Event in Chicago

Join the Community

How the Chicago Chapter Connects

Our events are intentionally designed to foster trust, insight, and meaningful relationships.

Intimate Dinners

Small group dinners curated by topic or industry to foster deepconnection.

Roundtables

Facilitated discussions on specific challenges Chiefs of Staff face.

Happy Hours

Casual gatherings to meet new members and reconnect with old friends.

1:1 Coffee Chats

We match you with other local members for individual connections.

PRO+ Members Get Access to all Chief of Staff Network Community, Events & Programs

COSC events are exclusive experiences designed for PRO members bringing together curated conversations, expert insights, & high-value networking within the global community.
Become a PRO Member

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