The two women first met at a dinner in Las Vegas last January hosted by Kristin Lemkau, the chief marketing officer of JPMorgan Chase. “We had an instant connection,” Ms. Huffington said. That night, she posted a photo of herself with her arm around a beaming Ms. Saint John on Instagram with the hashtag#thecoolkidsdinner.” The next month, Ms. Huffington attended Ms. Saint John’s 40th birthday party in Los Angeles. (Another Instagram opportunity: “Hard to imagine what she’ll do by 50!” she posted.)
“Sometimes it takes you months to get to know someone,” Ms. Huffington said. “With her, I felt like she has this incredible capacity for intimacy and for sharing her story and for sharing others’ stories.”
And, Ms. Huffington said, “She’s great at social media.”
Indeed, while women have long feared that putting family pictures on their desks might impede their climb up the corporate ladder, Ms. Saint John has broken the glass frame: posing in a bikini with her “baddies” on a beach; snapping a selfie as her daughter, now 8, tags along on a business trip; and posting the last red-carpet photo she took with her husband, Peter Saint John, who died of Burkitt lymphoma in 2013.
“I’ve been told that I overshare,” she said. “Sometimes I get criticized for it, but how else would I be if not all of me?”
Ms. Saint John knows it might seem overly calculating of Uber, which has been accused of fostering a
hostile work environment for women, to hire an African-American single mother to make over its public image. She doesn’t care. “To me, there’s no sense of tokenism because I know I can do the job — I’m qualified to do the job, I can do a
great job,” she said. “Being present as a black woman — just present — is enough to help exact some of the change that is needed and some that we’re looking for.”
She amplifies this presence with statement-making ensembles like the ruffled, lilac Marni skirt and crop top, gold-encrusted Chanel purse and stiletto heels she wore on a recent morning at Uber’s San Francisco office. “That’s my own personal thing,” Ms. Saint John said of her interest in fashion, so distinct from the hoodie aesthetic around her.
She has stood out from the crowd since her family settled in Colorado Springs when she was 12, after an itinerant childhood spent in Connecticut, Washington D.C., Kenya and Ghana, where her father was a member of the Parliament from 1979 until the 1981 coup d’état there. Her mother designed and sold clothes and ensured that Ms. Saint John and her three younger sisters stayed connected to their culture, especially once they moved to the Southwest.
“The first few months were really hard,” Ms. Saint John said. “Having a name that people can’t pronounce” — it’s BOZE-mah — “having a mom that refused to serve pizza on Friday nights when friends came over. She was like, ‘No you’re going to have this pepper soup, I don’t care if you’re sweating.’” (She’s come to appreciate that steadfastness: Accepting an award at an arts fund-raiser hosted by Russell Simmons this month, Ms. Saint John thanked her mother for ingraining her love of African culture.)
Ms. Saint John became captain of the cheerleading squad and track team. In her sophomore year, she ran for student council under the tagline “Ain’t Nothin’ but a Boz Thing,” inspired by her anthem of the moment, Dr. Dre’s “Nuthin’ but a ‘G’ Thang.”
“I just thought it was so cool, but nobody got it,” she said. She lost, “but it was a great lesson — you need to connect on your audience’s level, not on your own.”
Ms. Saint John attended Wesleyan University, ostensibly to prepare for becoming a doctor but managing to teach a class on Tupac Shakur, with a professor’s supervision, in her spare time. She got into medical school but lobbied her parents for a yearlong sabbatical. “They agreed, which was their mistake,” she said.
She moved to New York, and through a temp agency got gigs as a catering server and a receptionist for an Upper East Side dog-washing salon. She also began going to nightclubs, where she made friends with influencers like
Rene Mclean, who ran a D.J. boot camp. Her temp agency sent her to SpikeDDB, Spike Lee’s advertising firm. Mr. Lee had fired his assistant and wanted someone to answer phones while he looked for a new one.
“She walked in, she got the job,” he said. “It was evident that she was going to go places.”
Ms. Saint John went from making coffee runs to helping Mr. Lee brainstorm campaigns, like casting Beyoncé, who had just left Destiny’s Child, as Carmen in a Pepsi commercial.
“That became the turning point where, O.K., I can actually use my knowledge of pop culture, running around these streets with my friends, knowing the inside track on things, to help inform business decisions,” she said. She also met her husband-to-be, an advertising executive, in the company cafeteria.
After a stint selling smoking cessation products for GlaxoSmithKline, Ms. Saint John took a marketing job at Pepsi, coming up with projects like the “Pepsi DJ Division,” which included
D.J. Khaled.
In 2013, she orchestrated the halftime show Pepsi sponsored at the Super Bowl featuring Beyoncé. Four months later, her husband’s illness was diagnosed. Their daughter had just turned 4.
“Towards the end of his life, as everything started to fail, he was very adamant that I not stop what I was doing,” Ms. Saint John said. “He was telling me to hold his hands because he couldn’t grasp anymore, saying, ‘Promise me, you’re going to keep going.’”
On the 13th anniversary of their first date, Ms. Saint John posted a status update on Facebook, saying in part, “we reflect over our years together as he has a chemo cocktail and I drink red wine in a paper cup.” Mr. Saint John died in December 2013. Ms. Saint John, true to her word, kept going. In February 2014, Jimmy Iovine, a founder of Interscope Records, found out she was in Los Angeles for a sister’s wedding and requested a meeting at his house in Malibu. He had just started Beats Music, a streaming service, with her teenage idol, Dr. Dre. Who was Mr. Iovine? How did streaming work? She wasn’t quite sure, but she drove to the beachside residence.
“We ended up talking for four hours,” Ms. Saint John said. “I was raw. I needed something to give me some hope for the future. I needed something that could help me see further. When he was talking about all this newfangled stuff, I said: ‘That sounds like the future! I’m going to the future!’”
Ms. Saint John quit Pepsi and moved to Los Angeles as the head of global marketing for Beats. Her role expanded when Apple acquired Beats for $3 billion in 2014, and she came up with popular ad campaigns for Apple Music, like a
2015 commercial in which Mary J. Blige, Kerry Washington and Taraji P. Henson bond over post-breakup songs in a light and palm-frond-filled mansion (“Siri, play ‘I Will Survive,’” Ms. Washington says). Last year, Ms. Saint John
walked on stage at Apple’s developers’ conference — the first black woman to do so — blasting old-school rap and commanding the room of mostly white men to bounce to the beat.
Wired wondered, “Who the hell is this badass woman, and how did Apple keep her secret for so long?”
After hearing Ms. Saint John’s story of her Austin ride, “I had a flash — ‘Wow, she’d be great at Uber,’” Ms. Huffington said. “I thought she would be a great person to tell these amazing stories of our drivers, to touch people’s hearts, to bring more humanity to the brand.”
In May, Ms. Saint John and Travis Kalanick, an Uber founder and then chief executive, spent eight hours at Ms. Huffington’s home in Los Angeles, discussing what she might do for the company, both grand and simple.
“I think I might need to wear a disguise, but I want to drive,” she said. “What happens when someone gets in the car and they’re upset? Is that a moment? Do you just stay quiet or do you talk?”
Mr. Kalanick would step down as chief executive a month later. The hunt is on for his successor. But whoever it is will have Ms. Saint John helping steer from the passenger seat, stilettos and speakers on.
“Why wouldn’t they want her?” Mr. Lee said. “She’s just what the doctor ordered, the stuff they were going through. She’s a godsend for Uber.”
