Skip to Main Content

The Executives’ Club of Chicago has long been the stage where the most consequential leaders share what they’ve learned — the decisions that tested them, the convictions that sustained them, and the wisdom they’ve earned. Christie Hefner belongs in that company.

As Chairman and CEO of Playboy Enterprises for nearly two decades, Hefner did what few leaders in any era have managed: she took one of the most recognizable — and most scrutinized — brands in the world and built it into a diversified, globally relevant enterprise. Under her leadership, Playboy expanded into international licensing, digital media, and new consumer markets, growing revenues and reach well beyond the magazine that made the name famous. She was thinking in platforms and partnerships before those words entered the mainstream business lexicon.

But what makes Christie Hefner an Iconic Leader isn’t just the business results. It’s the combination of intellectual courage, values clarity, and strategic discipline she brought to every role she held. At a time when it was neither easy nor popular, she was a forceful advocate for LGBTQ+ equality, women’s advancement, and civic engagement — not as side pursuits, but as expressions of who she is. Christie also led efforts around first amendment rights and legalizing cannabis. She led from the front, spoke her mind, and built a career defined not by conformity, but by conviction.

Following her tenure at Playboy Enterprises, Christie has focused intentionally on what she describes as “paying it forward” — investing in the next generation of leaders through teaching, mentorship, and civic engagement. She lectures at the University of Chicago Booth School of Business on leadership and governance, serves on the Advisory Committee for the University of Chicago’s Leadership in Society program, helped launch Press Forward Chicago, and continues to advise CEOs and senior executives navigating growth, transformation, and complexity.

That continued commitment to leadership — not just as a business discipline, but as a civic and cultural responsibility — is part of what makes Hefner’s perspective so relevant today. Her career spans media, governance, public discourse, social change, and corporate transformation, giving her a uniquely expansive view of what leadership requires in moments of both opportunity and scrutiny.

This is a conversation Chicago’s senior executives will not want to miss — a chance to hear directly from a leader who has seen it all, done the hard work, and has something meaningful to say about what it takes to lead with both boldness and integrity.

This conversation examines how executives can navigate pressure, ambition, and leadership responsibility without sacrificing their health, relationships, or sense of self — and why the future of leadership may depend less on endurance and more on how leaders sustain themselves and others over time.

Individual Pricing:
Members: $150
Nonmembers: $300
Table Pricing:
Members: $1,350
Nonmembers: $2,700

The Executives’ Club of Chicago partners with members of the media to share stories of leadership and impact. For interviews or event coverage opportunities, please contact our Head of Brand & Communications Katy Broom.

For more information and sponsorship opportunities, please contact our Head of Partner Activation Ella McCann.

Season Sponsors