Will Smith and Jada Pinkett Smith’s Westbrook Media Taps Three Execs for Key Roles (EXCLUSIVE)

Todd Spangler
·3 min read
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Westbrook Media, the digital studio arm of Will Smith and Jada Pinkett Smith’s media company, has tapped three veteran execs for senior roles.

Longtime producer Sterling Milan (above left) joins the company full time as head of original content, after recently operating as an in-house executive producer, showrunning and directing series and specials for Westbrook Media originals.

Jabari Hearn (above center), previously in marketing roles at Lyft, Google and Nike, joins Westbrook Media as senior VP marketing for brand and entertainment. He’ll work closely with Drew Miles (above right), formerly with Variety, newly named to the position of senior director of business development and partnerships for the company.

The trio of execs begin their new roles effective immediately. Hearn reports to Westbrook Media president Brad Haugen; Milan reports to Lukas Kaiser, SVP, head of content; and Miles reports to Ashley McCollum, SVP, revenue and strategy.

“Both Jabari and Drew have demonstrated their innovative approach to brand storytelling and partnerships,” Haugen said in a statement. “We are excited for the two of them to bring their ingenuity and prowess to the team as we continue to expand our growing marketing services and work with brands and entertainment partners to connect to their consumers in an impactful way.”

Regarding Milan, Kaiser commented, “I’ve been a friend and a fan of Sterling’s for over a decade — and bringing him on to lead the creative side of production on numerous projects over the past few months has been a joy. We’re thrilled to bring him into the Westbrook Media family to help bring our robust development slate to life.”

Milan has over 16 years of experience “creating innovative content with strong cultural impact,” the company said. Most recently, he executive produced Westbrook Media and Jaden Smith’s racial justice series “The Solution Committee” for Snapchat. He also served as a co-executive producer on the Westbrook Media documentary special “Will Smith: Off the Deep End” for Discovery’s 2020 Shark Week event.

In addition, Milan has directed multiple projects including the film “About the People” starring Michael K. Williams and Diggy Simmons, which is currently being optioned for series, and feature documentary “She Did That” for Netflix. He is currently directing a behind-the-scenes documentary for Disney Plus about NetGeo’s “One Strange Rock” (which was hosted by Will Smith).

Hearn most recently was Lyft’s VP of brand, where he led the ride-hailing company’s launch of LyftUp, an initiative to expand transportation access to those who need it most. That included securing a partnership with LeBron James to help bring bikeshare access to youth across the U.S.

Prior to Lyft, Hearn led global marketing for mobile hardware at Google. In that role, he helped launch the Google Pixel 2 and 3 smartphones, which included award-winning campaigns with Childish Gambino. Prior to Google, Hearn spent more than a decade at Nike, where he was brand director for its football, baseball and training consumer product lines, overseeing campaigns including the Nike Women’s Half Marathon and the Nike x NFL partnership. Earlier in his career, he led strategy for clients such as Adidas and Brand Jordan at Chiat Day and Wieden + Kennedy.

Miles most recently was VP of global brand partnerships at Variety, leading branded content efforts with entertainment companies including Warner Bros., Participant Media, Amazon Studios, Universal Pictures, DreamWorks, Apple TV Plus and Disney. With over 15 years of experience in sales, marketing, and business development, he has worked on projects with media brands including Upworthy, the New York Times, Huffington Post and Oprah.com, including the launch of OWN: Oprah Winfrey Network.

Westbrook Media is a subsidiary of Westbrook Inc., the media venture launched in 2019 by founders Jada Pinkett Smith, Will Smith, Miguel Melendez and Ko Yada, focused on “empowering artists to tell stories that connect with a global audience,” according to the Calabasas, Calif.-based company.

Pictured above (l. to r.): Sterling Milan, Jabari Hearn, Drew Miles

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