She recognized that Uber didn’t have a tech problem, but a brand problem. It was her job to “[get] into the beat of the brand, and what was hurting” it, as she put it. “Nobody had a plan. There was nothing happening except for whatever I dreamed up.”

Under Saint John’s leadership, the brand repositioned itself with a campaign starring the then-newly appointed CEO Dara Khosrowshahi promising to steer the company in a better direction. The brand slowly but surely made strides.

Overcoming tragedy to make a new start

Saint John’s self-assuredness has been a theme throughout her professional life—and in her personal life, too. 

In 2013, she lost her husband of 10 years, Peter Saint John, to cancer. Still in the throes of grief, Saint John decided to rearrange her life, quitting her job as head of music and entertainment marketing at PepsiCo and leaving New York for the west coast. 

“My husband had been dead for four months when I resigned and moved across the country from New York to Los Angeles to start working for Jimmy Iovine and Dr. Dre” at Beats, she said. “Everyone thought I’d lost my mind. But the truth of the matter is that I needed to do it for myself. People didn’t understand what I was dealing with, and they thought that the answer was in hiding and laying down. And I don’t fault anybody who wants to do that when you suffer a loss like that, but for me, I needed to get back up. So I had to go.”

Then in the spring of 2014, Beats was acquired by Apple. Before long, Saint John found herself sitting in the tech giant’s headquarters in Cupertino. “Tim [Cook] said, ‘Well, you should actually just run iTunes in Apple Music,’” she recalled. “And I was like, ‘Oh, shit.’”

Just like that, her life was off in a new direction again—thanks in large part to her unwavering trust in her own intuition.

“There are so many myths about what it takes to be a leader,” she said. “Sometimes it’s misunderstood that you have to have a clear path in order to become a leader, in order to rise to the top again, and again, and again. What I want to show is the fact that I am human, and that terrible things have happened in my life, and I have found ways to navigate those tragedies and that loss and grief in order to not just survive, but to thrive.”

She added: “The adage is, ‘Look for the light at the end of the tunnel.’ That sounds so stupid. It is much better to have a light on your person,” she said. “That way, you can look around, see what’s coming, get rid of monsters, all that stuff. I have had much more success being my own light, my own champion, my own advocate, than searching for it in somebody else.”