Alicia Boler Davis spent nearly 25 years at General Motors Co. rising up the ranks from a manufacturing engineer to running global manufacturing and labor relations for the automobile giant.

“I never thought I’d leave,” said Ms. Boler Davis, who started at GM in 1994. “At GM, I had an opportunity to really contribute, and to have an impact. Every two years, I had an opportunity to do something different.”

During her career, she reported to GM Chief Executive Mary Barra, and at one point ran the company’s OnStar emergency-alert system division. She was the most senior Black executive in the entire automotive industry.

But she started to have a nagging feeling that to continue growing, she had to move beyond the company she had called home for most of her career.

In 2019, she joined Amazon.com Inc. as vice president of customer fulfillment, quickly being promoted to join then-CEO Jeff Bezos‘ most senior group of advisers, called the “S-Team,” and elevated to senior vice president, with 800,000 people in her organization across warehouses, sustainability, customer-service and other groups.

Less than a year after she joined Amazon, the coronavirus set in. But Ms. Boler Davis had built a knack for managing through tough situations. At GM, she headed up product quality when the company had a damaging ignition-switch recall. Ms. Boler Davis made the decision to recall 1.6 million vehicles.

At Amazon, Ms. Boler Davis was faced with a rapidly shifting pandemic that affected the company’s hundreds of thousands of employees, as well as millions of customers.

Ms. Boler Davis and her team had daily meetings to address how to keep employees safe while getting products to customers. At one point, she had to rip up a 3-foot social-distancing order in the company’s warehouses over a weekend when CDC guidance showed that 6 feet was the better protocol.

“I learned crisis management, quite frankly, at both companies,” said Ms. Boler Davis.

In early 2022, Ms. Boler Davis says she started to consider the next five years of her career. An executive recruiter called her about digital pharmacy startup Alto Pharmacy. She had never heard of the company until that phone call.

But, after meeting with Alto’s founders—two former Facebook employees who wanted to disrupt the pharmaceutical industry—she said she came to believe in the seven-year-old company’s mission.

“This isn’t a Fortune 500 CEO job, which was probably the expected thing for me to do,” said Ms. Boler Davis, who was interviewing for such roles when Alto approached her. “I’ve never done what was expected. I wanted to do something that I felt could make a difference in a different way.”

In September, she started as CEO of Alto, a “unicorn”—or startup valued at $1 billion or more—that counts SoftBank Vision Fund as an investor and competes with the likes of Capsule, Walgreens and even Amazon Pharmacy.

Here are four of her most trusted advisers:

Bill Boggs

Retired GM executive

Ms. Boler Davis met Mr. Boggs in 1999, when she was working as a plant planner at a troubled GM plant. Mr. Boggs was brought in from Ford Motor Co. to turn the plant around, and immediately recognized Ms. Boler Davis’s talent.

Over the decade Ms. Boler Davis worked for him or his organization, Mr. Boggs promoted her a number of times, sometimes just a few months after a previous promotion. Occasionally, Ms. Boler Davis questioned if she was ready for the roles he gave her.

Four months after he promoted her to office manager on the logistics side of the business, Mr. Boggs commended Ms. Boler Davis on the job she had done. The team was no longer running out of parts, because of her attention to detail. “You’ve done all these things that no one would have the courage to do,” she recalls him telling her. He then said he needed her on the quality team—another promotion. “I said, ‘Bill, I don’t know if I’m ready.’ He said ‘trust me, you’re ready.’”

In 2007, he promoted her to plant manager of one of GM’s most important plants.

Ms. Boler Davis said she learned about recognizing talent and placing bets on talent from Mr. Boggs, who also backed and promoted other women at GM.

Ben Slivka

Angel investor, Retired Microsoft and Amazon executive

Ms. Boler Davis met Mr. Slivka in 2014 when she gave the keynote address at Northwestern University’s graduation ceremony for engineers. At the time, Mr. Slivka was on the board of trustees, which Ms. Boler Davis would later join. Since that meeting, Mr. Slivka has pushed Ms. Boler Davis to move beyond her comfort zone, she said. “He challenged me for a number of years,” recalls Ms. Boler Davis. “He’d say, ‘You’re too comfortable. You’re just going stay there and just build cars for the rest of your life?’”

Whenever Ms. Boler Davis got a new promotion at GM, Mr. Slivka would act unimpressed, telling her she was ready for something bigger. In 2018, Ms. Boler Davis started to have an uneasiness that she was too comfortable at GM and it might be time to try something new. Over breakfast, she told Mr. Slivka that an Amazon recruiter had contacted her. He responded: “If his name isn’t Jeff, you’re not talking to the right person,” referring to Mr. Bezos and then-Amazon Consumer CEO Jeff Wilke. Mr. Slivka was friends with Mr. Wilke, and introduced him to Ms. Boler Davis.

The rest was history, she said. After the meeting with Mr. Wilke, she joined Amazon. She says she likely wouldn’t have ended up at the e-commerce giant if not for Mr. Slivka pushing her.

Patti Poppe

CEO, PG&E Corp.

Ms. Boler Davis met Ms. Poppe in 1998 when she was assigned to work in a GM plant where Ms. Poppe was a leader.

“What I learned from her is about leading with empathy, and about building a team piece by piece and the importance of the people on your team to being successful,” said Ms. Boler Davis. She recalls Ms. Poppe being tough, but also being empathetic and having fun. Ms. Poppe also set an example of being a senior leader in a male-dominated environment, and made an effort to help other female employees at GM become leaders, said Ms. Boler Davis.

The two women stayed in close contact over the years, with Ms. Poppe even being part of Ms. Boler Davis’s wedding party. Ms. Boler Davis has relied on Ms. Poppe for all types of advice. “I also learned from her taking risks in her career,” said Ms. Boler Davis, who followed the way Ms. Poppe took her own risk when she left a senior role at GM in 2005 to join the energy industry.

She called Ms. Poppe when she was leaving GM and leaving Amazon to get her opinion, she said.

Kevin Williams

CEO, GAA Manufacturing and Supply Chain Management, former GM executive

Ms. Boler Davis’s first interaction with Mr. Williams was an unsolicited phone call from the then-GM executive early in her career. “He said ‘Hey Alicia, I’m Kevin Williams. You don’t know me; I know you. I’ve been following your career, I just want to be a resource for you to help you along your journey,” she recalls. Ms. Boler Davis did know who Mr. Williams was. She looked up to the most senior Black executive at the company, she said.

Over the years, the two would have regular check-ins and lunches. Mr. Williams helped Ms. Boler Davis strategize about decisions in her roles at GM and job offers she got throughout the company and outside of it.

One of Mr. Williams’ biggest lessons was around being excellent, she said. Mr. Williams used to say “excellence ain’t easy,” she recalls, but impressed upon her that she had to be excellent to grow and that she had to continually raise the bar for herself.

“I learned a lot from Kevin about mentoring, being a teacher, being available,” she said. Ms. Boler Davis has adopted the executive’s move of calling talented employees out of the blue to offer mentorship, and has been involved in women’s networks and diversity initiatives at the companies she’s worked at to foster talent and serve as a mentor.

This story has been published from a wire agency feed without modifications to the text.