In an era where success is often flattened into sound bites and spectacle, The CEO Club arrives with a quieter, more complex proposition: what if leadership were observed not at its finish line, but in motion—mid-decision, mid-doubt, mid-course correction?

The Amazon Prime series follows a group of women CEOs across vastly different industries, offering rare access to the moments that rarely make headlines: deliberation, recalibration, and the emotional labor behind authority. Among them is Dee Ocleppo Hilfiger, a figure whose career spans entrepreneurship, design, and creative leadership. As Creative Director of Judith Leiber, founder of her namesake shoe and accessories line, and the woman behind the clothing label DO, Ocleppo Hilfiger’s professional life has been shaped by both reinvention and resolve.

What makes her participation in The CEO Club compelling is not simply her résumé, but her willingness to allow the camera into the unscripted spaces of leadership—where outcomes are uncertain and composure is often earned rather than assumed. The series does not position power as a fixed state, but as a practice: one that requires steadiness under pressure, adaptability in the face of disruption, and the humility to acknowledge that even the most seasoned leaders are still learning.

In the conversation that follows, Dee speaks straightforwardly about her experience on the series, reflecting on adaptability, visibility, and balance.