Who We Are
CEO Life is a private executive leadership community uniting established CEOs, founders, and senior executives across cities and regions, and increasingly around the world. Members are accomplished leaders who value discretion, depth, and stewardship, and our chapters give them a place to gather, grow, and give by building real relationships instead of simply collecting contacts.
About the Role
CEO Life is looking for Chapter Directors to help build our Chicago, IL community. This is an independent, commission-based position for someone who knows the local business community, enjoys bringing successful people together, and wants to help grow a membership of CEOs, founders, and senior executives.
As a Chapter Director, you'll report to the Chapter President and take ownership of developing new member relationships in the Chicago market. You'll introduce qualified leaders to the community, help create events members look forward to, and make sure every new member feels welcomed, known, and connected.
For the right person, this is an opportunity to be among the founding leaders of a growing chapter, build recurring income from the members you bring in, and establish yourself as a connector in the Chicago business community.
What You’ll Do
- Develop relationships with CEOs, founders, business owners, and senior executives in Chicago and invite the right people into the community.
- Work with the Chapter President and fellow Directors toward a combined chapter goal of 4+ new members per month, with clear expectations and accountability.
- Bring in new members consistently each month through your network, referrals, events, and local business relationships.
- Welcome new members, learn about their businesses and interests, and make valuable introductions that keep them engaged.
- Host and drive attendance to CEO Life's monthly Chicago events, bringing guests who strengthen the room and introduce prospective members to the community.
- Partner with the Chapter President and corporate team on event ideas, venues, and experiences members talk about afterward.
- Build relationships throughout the Chicago business community and represent CEO Life at events and in the market.
- Use CEO Life's CRM, member platform, outreach tools, and training to manage your pipeline and follow up professionally.
- Serve as a visible local representative of CEO Life, including occasional participation in social media and chapter content.
Requirements
- 3+ years of experience in a relationship-driven role involving some combination of business development, sales, events, hospitality, community building, or entrepreneurship.
- Must currently live in the Chicago, IL area.
- A strong existing network within the Chicago business community is valuable, but equally important is the ability to quickly build authentic relationships with successful business leaders.
- A natural ability to connect people and recognize opportunities where an introduction can create value.
- Relationship-based sales skills and the confidence to ask for the business without making the interaction feel transactional.
- A warm, engaging presence and the ability to make people feel welcome, known, and connected.
- Strong organizational skills and the self-direction to manage your own pipeline, follow-up, and commitments.
- Comfort representing an organization publicly, including speaking in front of groups and appearing occasionally on camera or social media.
- An entrepreneurial mindset and genuine interest in building something within your local business community.
What Success Looks Like
Within your first several months, you'll have built a consistent pipeline of prospective members, brought your first new members into the chapter, established strong relationships with existing members, and become a reliable contributor to the monthly Chicago events.
Longer term, success means helping the chapter consistently add 4+ new members per month while contributing to the kind of member experience that drives engagement, introductions, referrals, and retention.
Benefits
- An independent, commission-based role with uncapped earnings tied to new member production. Compensation potential for membership sales only:
- 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 opportunity to help build one of CEO Life's newest local communities from the ground up
- The opportunity to join CEO Life at an important stage of growth, with a vision to reach 50,000 leaders across 150+ U.S. and global chapters by 2030
- A chance to establish yourself as a connector in your market while building a network that grows alongside CEO Life
Skills Required
- Real relationships with founders, CEOs, and executives in Chicago
- Track record in business development, sales, or entrepreneurship
- High emotional intelligence and natural relationship-building ability
- Presence and credibility with senior decision-makers
- Independence to manage an individual book of business
- Ability to contribute positively to an executive leadership team
- Ability to enroll 3–10+ new members monthly
- Ability to host and drive attendance at monthly chapter experiences
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What We Do
CEO Life is a private, curated executive leadership community for CEOs, founders, entrepreneurs, and senior executives. It connects like-minded leaders across local, national, and global networks through meaningful relationships, business networking, leadership development, mentorship, and recurring gatherings. The organization also promotes business growth, collective impact, and philanthropic activity, while operating as an exclusive social club with city-based chapters for members.
