From the mailroom to the boardroom at UPS Canada

Dexter's climb to become UPS's first female Canadian leader began as a package handler at 18

- JARED LINDZON

UPS Canada president Stephanie Dexter, seen at the UPS sorting facility in Brampton, took the helm of Canadian operations as the company grappled with a post-pandemic slowdown.

In 1989, Stephanie Dexter took a part-time job as a package handler for UPS in Ontario, Calif.; 35 years later, she runs the company’s Canadian operations from the province that shares that city’s name.

The then-18-year-old’s plan was to earn enough to fund her political science and economics degree at San Diego State University on the way to law school. After completing the program and the LSAT, however, Dexter ran into some financial challenges. That’s when her manager proposed a different path.

“I couldn’t afford to quit my job and go to school full time, take the kind of loans that I was going to need to take, and have no medical benefits,” she says. “I just decided it was too much of a risk, and my boss came to me and said, ‘we want you to be a full-time supervisor,’ and so I went full-time.”

The Southern California native spent the next 35 years climbing the ranks of the Atlanta-based shipping giant, including two years as an operations manager in the United Kingdom, and three as president for the Northern Plains District, which includes six American states.

Though she never got that law degree, Dexter earned an MBA from Louisiana State University shortly before being named president of UPS Canada in 2021, where she now oversees roughly 13,000 employees across 63 facilities.

UPS isn’t just one of the biggest names in the industry, it’s one of the largest companies in the world, with operations in over 200 countries and territories.

It occupies the 45th spot on the Fortune 500, with global revenues topping $91 billion (U.S.). Last year the company’s 500,000 employees delivered 5.7 billion packages, or 22.3 million a day.