Rachel Webber’s journey showcases her rise from Playboy to Paris Hilton's executive team, marking her influence in shaping a multimedia brand that resonates globally.

When thinking of Paris Hilton, images of signature Juicy Couture tracksuits and glamorous red carpet events might come to mind. However, the modern Paris Hilton has evolved into a savvy entrepreneur, a passionate advocate, and a pop culture icon who leads a multimedia brand with a worldwide vision. Much of this transformation can be credited to Rachel Webber, the Chief Brand and Commercial Officer at Paris Hilton’s 11:11 Media.

Webber’s path is just as vibrant as Hilton’s, featuring a career that spans National Geographic, Tumblr, and Playboy. In a conversation with Karen Finerman on the How She Does It Podcast, Webber discusses how her current role may be the most impactful yet.

Paris Hilton: The Original Influencer, Evolving

At 11:11 Media, Webber plays a key role in helping Hilton realize a vision that mirrors Disney's extensive reach. “She’s always exploring new avenues. She's a born brand creator. She thinks ahead. She truly is the original influencer,” Webber states about Hilton.

And indeed, Hilton has made strides. She recently debuted her 30th fragrance, unveiled a skincare line, and is diving into immersive entertainment. Her upcoming music documentary, Infinite Icon, allows fans to experience her journey in a groundbreaking 4D format, complete with holograms and sensory effects in theaters.

Transforming Struggles into Strength

“Women our age understood the humor behind the persona she crafted,” Webber reflects on Hilton. “The Simple Life ditzy blonde character had a relatable charm.”

Now, that persona is evolving into a narrative of empowerment, entrepreneurship, and societal impact. With a dedicated social justice initiative and a content collaboration with iHeartRadio, Hilton’s 11:11 Media is reshaping the concept of a purpose-led enterprise.

Leading with Purpose and Compassion

For Webber, effective leadership hinges on clarity, accountability, and nurturing culture. At 11:11 Media, she implements OKRs (objectives and key results) to keep her team aligned while promoting transparency and teamwork. “I find it most effective when everyone is part of the journey,” she shares.

What stands out is Webber’s candidness about challenges like burnout, reinvention, and the significance of a balanced life. After her time at Playboy, she took four months off, returned to New York to reconnect with family, and focused on dating with intention. “New York definitely has a different allure,” she jokes.

Ultimately, the narrative of Paris Hilton’s transformation is also a reflection of contemporary womanhood. It’s about claiming your own story, creating wealth on your own terms, and boldly pursuing your ambitions without waiting for validation.

Webber summarizes it well: “At the core of our mission is a powerful impact platform, and spreading a little magic wherever Paris goes is our goal. While it sounds delightful, it carries significant meaning.”

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