Bozoma Saint John has often found herself in the middle of some of the biggest stories in technology and entertainment.
The marketing executive was a key figure in Apple’s acquisition of audio company Beats, then jumped to Uber at the height of the ride-share firm’s reckoning with a toxic culture that had imperiled its business. Now, she’s a senior leader at Endeavor, the entertainment and talent firm that’s looking for financial footing after canceling its initial public offering of stock last week.
Speaking Wednesday at HubWeek, Boston’s annual ideas festival, Saint John said even she has been surprised by the wild turns her career has taken.
“I have truly followed my heart, and while that sounds maybe flip, and maybe not realistic, that is true,” she said. Even her mother has advised her against taking some of the jobs she’s held, Saint John said. “No one has been like, ‘That’s a good idea. Go and do that thing.’ Like never, ever.”
Saint John appeared onstage for a taping of Harvard Business Review editor Amy Bernstein’s “Women at Work” podcast.
She told a room packed with professional women that they should listen to their friends, family, and mentors when making a big career decision, but she advised them to ultimately trust their instincts.
Chances are, she said, you’ve already make up your mind, anyway.
“Even if people are like, ‘Eh, that’s a bad idea, you should probably do it,’ ” she said.
Saint John is one of the highest-profile women of color in the corporate world, with a major social media presence and a forthcoming Starz television series called “Bozoma: Being Badass.”
In a wide-ranging interview with Bernstein, Saint John discussed the many personal and professional challenges she has faced while building her career. Her husband, Peter, died of cancer in 2013, leaving her to raise their then 4-year-old daughter.
Saint John said people should embrace their whole lives in the workplace, as she has, because she wants her child to know that her work is a product of her personal life.
“Because of my experience as a mom, because of my experience as a widow . . . I’m a better person and a better executive,” Saint John said.
Meanwhile, she’s navigating a corporate world that is mostly white and male. She shared some advice on how to navigate environments where there aren’t many people like her.
Saint John described leaving Uber for Endeavor in part because of a culture prone to microaggressions — everyday verbal and emotional indignities directed, sometimes unintentionally, toward marginalized groups.
“The challenges of being black, of being a woman in an environment like that were too overwhelming,” she said. “And at some point you realize that you can’t sacrifice yourself for the cause.”
She said it can be hard to know when to speak up, when to stay quiet, and when to just pack up and leave.
“I try to address [transgressions] one at a time, even if it feels petty sometimes,” she said. “I do it on the side, and if they’re not listening, I’ll do it publicly.”
Someone in the audience asked Saint John how to handle coworkers who treat women or people of color as hires made just for diversity, rather than on their own merits.
Saint John said the best way to counter such attitudes is to do an excellent job and to show confidence.
“You can pretend that this is a diversity hire or a token hire. But I know I’m going to outwork you. I know I’m going to have better ideas than you. I know I’m going to succeed more than you do,” she said.
“I don’t mind proclaiming that. Because sometimes it requires the extra bravado, even when it means not making all the friends.”
Andy Rosen can be reached at email@example.com.