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Deirdre O’Brien has had the sort of career that many people dream about. In January 1988, as a newly minted college graduate, O’Brien took a job at Apple working on production of the Macintosh SE, an early iteration of the classic Macintosh line that introduced personal computers to lay people. More than three decades later, Apple is a trillion-dollar company—and O’Brien is one of the highest ranking executives at its helm.
In 2017, O’Brien became the head of people, reporting directly to Tim Cook, which means she oversees everything from talent development and recruiting to benefits and compensation for more than 137,000 employees. Last year, when former retail chief Angela Ahrendts stepped down, O’Brien’s role expanded to include leading Apple’s retail division, which operates upwards of 500 stores across the world and employs more than 70,000 workers.
Since the coronavirus hit, O’Brien has been tasked with navigating how—and when—to reopen Apple’s retail stores, which have long been a hub for both sales and customer service. In March, Apple shuttered all retail stores outside of China to do its part in curbing the spread of coronavirus. As of this month, Apple has opened nearly 100 stores across the world, but with reduced occupancy and the option of curbside pickup to abide by social distancing measures. Customers and staffers alike must wear a face covering, and temperature checks are required at the door.
As the head of people, O’Brien has also steered many of the company’s diversity and inclusion efforts. Like other tech companies, Apple has struggled to make significant progress in its corporate ranks, though it has made greater strides than its peers due to its retail arm. In 2018, more than 30% of Apple’s new hires were underrepresented minorities; across the company, 9% of employees are black and 14% identify as Hispanic. Those figures are even higher in the retail sector, where 15% of workers are black and 21% are Hispanic.
“Apple has changed my life and supported me in so many ways, not least of which is the fact that I met my wife here,” O’Brien says. “I feel a deep responsibility to support and carry our culture forward for everyone else—for anyone who comes from a background that has been historically underrepresented.”
After talking to new parents—especially women—O’Brien felt there was still more Apple could do to ease their transition back to work, even beyond the company’s 16-week paid leave policy. That’s why Apple introduced a return to work policy last fall that gave new parents an additional four-week grace period when they returned from leave, which allows them to work part-time and set their own hours—all while being paid like full-time employees. The benefits apply to retail workers, as well. For parents who adopt, Apple nearly tripled its financial assistance to $14,000 and expanded leave.
“I think many times working parents feel like they need to deal with that quietly and make it seem perfectly seamless,” O’Brien said at the time. “We all know life is complicated. So [we’re] making it really clear that we’re supporting them in that journey.”
In just over a year, O’Brien—who helped launch Apple’s inaugural online and retail outposts earlier in her career—has made her mark on Apple’s retail footprint, too, launching seven new locations around the world and transforming 16 existing locations. The most notable renovation was for the Fifth Avenue location in New York City, which nearly doubled the flagship store’s footprint and flooded it with natural light and foliage. The store’s grand reopening was timed to the launch of the iPhone 11 back in September, with O’Brien, Cook, and other Apple executives in attendance.
But for all her professional accolades, O’Brien has said one of the moments she is most proud of dates back to her twenties—when she came out a few years into her tenure at Apple. “Early on, even though Apple has always been a very open-minded place, coming out was a really tough decision for me,” she says. “I worried a lot about how I would be treated because I was different from the prevailing norm. I’ll never forget how hard it was to take that step, but it is a decision I’ve never once regretted.”
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