From Playboy to Paris Hilton: Rachel Webber’s C-Suite Rise

From Playboy to Paris Hilton: Rachel Webber’s C-Suite Rise


From National Geographic to Paris Hilton’s 11:11 Media, Rachel Webber’s executive journey is one of bold pivots and lasting impact.

When we think of Paris Hilton, we might picture the iconic Juicy Couture tracksuits, the glitzy red carpets, or her trailblazing stint on The Simple Life. But today’s Paris Hilton is no longer just a reality TV star. She’s a savvy entrepreneur, an advocate, a pop culture mogul — and the CEO of a multimedia brand with global ambitions. And behind much of that evolution is Rachel Webber, Chief Brand and Commercial Officer at Paris Hilton’s 11:11 Media.

Webber’s own journey is as dynamic as Hilton’s, with a resume spanning National Geographic, Tumblr, and Playboy. As she shares with Karen Finerman on the How She Does It Podcast, it’s her latest role that might just be her most transformative yet.

Paris Hilton: The Original Influencer, Reinvented

At Paris Hilton’s 11:11 Media, Webber is helping Hilton execute a vision that’s nothing short of Disney-sized. “She’s always tinkering. She’s a natural brand builder. She sees around corners. She really is that kind of OG.” Webber says of Paris Hilton.

And build, she has. Paris recently launched her 30th fragrance, announced a new skincare line, and is leaning hard into immersive entertainment. Her upcoming music documentary, Infinite Icon, doesn’t just tell her story — it lets fans experience it in 4D. Think: holograms, scent effects, and full-sensory performances in theaters.

Turning Pain Into Purpose

Webber speaks candidly about how Hilton has reclaimed her narrative. Her 2020 documentary exposed the abuse she endured as a teen in “troubled teen” programs, followed by a best-selling memoir and now her second pop album, executive produced by Sia, featuring stars like Megan Thee Stallion and Meghan Trainor.

“Women our age were kind of in on the joke that was a character she created,” Webber says of Hilton. “That Simple Life dumb blonde character. And I think there was something really relatable for people.”

Now, that brand is evolving into one of empowerment, entrepreneurship, and impact. With a team that includes a dedicated social justice arm and an ongoing content partnership with iHeartRadio, Paris Hilton’s 11:11 Media is redefining what it means to build a purpose-driven empire.

Leading With Intent and Empathy

For Webber, leadership is about clarity, accountability, and culture. At Paris Hilton’s 11:11 Media, she uses OKRs (objectives and key results) to keep the team focused while fostering transparency and collaboration. “I see it as most productive if you’re taking everyone on a journey,” she says.

But perhaps what’s most refreshing is Webber’s honesty about burnout, reinvention, and the importance of a holistic life. After leaving Playboy, she took four months off, moved back to New York to be near her family, and to date more intentionally. “There’s more sex appeal in New York,” she laughs.

In the end, the story of Paris Hilton’s reinvention is also a story about modern womanhood. About owning your narrative, building wealth on your terms, and not waiting for anyone’s permission to make bold moves.

As Webber puts it: “Underpinning all of this, we have an incredible impact platform, and leaving a sparkle everywhere Paris goes is her mission. Which sounds very fun, but has real profound meaning.”

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