CEO Life Chapter Director - Chicago

Chapter Director — Chicago

CEO Life | Private Membership Club for CEOs, Founders & Entrepreneurs

Location: Chicago, IL
Type: Independent Partner / Commission-Based
Reports To: Chapter President

The Club

CEO Life is a private invite-only membership community built for CEOs, founders, and leaders who want more than a network.

We're not a mastermind. We're not a leads group. We're the room where ambitious people actually want to be — happy hours and business round tables, fine dining and theatre, courtside seats and concerts, and destination trips worth traveling for. Rooted locally. Connected nationally. Built on the belief that trust forms first, and opportunity follows naturally.

Membership is by application and invitation only. What we're building in every city is simple: Gather. Grow. Give.

The Opportunity

We're building the Chicago chapter, and we're looking for four Chapter Directors to build it.

You'll be part of a five-person Executive Leadership Pod shaping how this club shows up in your city — who's in the room, what the nights look like, and how members feel when they walk out. You'll help assemble our Chicago chapter: the curated group of leaders who set the culture, tone, and rhythm of a chapter before anyone else arrives.

You'll do it with the brand, the systems, and the national momentum behind you. And you'll build a recurring income stream from every member you bring in.

What You'll Own

Your revenue streams:

• Membership enrollments and renewals
• Performance bonuses
• Partnerships and sponsorships

Your responsibilities:

• Curate membership — invite the right people, protect the room
• Build authentic relationships across your industry niche
• Enroll 3–10+ new members monthly (top performers average 7+)
• Host and drive attendance to the chapter's signature monthly experiences
• Work with your Pod to create experiences members talk about for months
• Compound your income through the relationships you build

Who You Are

You're the person who already knows everyone worth knowing — and who people trust with an introduction.

You bring:

• Real relationships with founders, CEOs, and executives in Chicago
• A track record in business development, sales, or entrepreneurship
• High emotional intelligence and a natural instinct for connecting people
• Presence that earns respect in a room full of decision-makers
• The independence to run your own book, and the character to make a team better
• Genuine belief in depth over display, connection over transaction

Why This Is Different

The membership sells itself when the room is right. Members join for the people. Your job is to find them.

Real infrastructure behind you. Full onboarding and leadership development, access to our CRM and member platform, national marketing and brand recognition, LinkedIn outreach systems, and proven playbooks from top-performing Directors.

Ownership, not a paycheck. Recurring revenue that compounds. No earnings cap. A protected niche within your market. A clear path to expanded leadership.

You're early. 35+ chapters today. 100 U.S. locations by the end of 2028. 50,000 leaders connected globally. And in one of the fastest-growing entrepreneurial city in the country, the timing has never been better. The vision is bigger than any one chapter, and the people who build the foundation get the upside.

Earning Potential

Compensation Potential For Membership Sales Only

Performance Scenarios:

• Solid Performer (3 members/month): $54,000/year
• Strong Performer (5 members/month): $90,000/year
• Top Performer (7+ members/month): $126,000+/year

Plus additional revenue from renewals, partnerships, and special initiatives.

The Founding Chicago Chapter Starts With You

We're selecting four Directors for Chicago who understand that the strongest communities aren't sold, they're felt.

If you've spent your career bringing people together and never got paid what it was worth, this is the seat.

Apply now.

CEO Life is building the future of executive connection through three pillars: Gather (authentic relationships), Grow (leadership development), and Give (community impact). Join us in creating something extraordinary.