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For 30-plus years, Deirdre O'Brien has been giving Apple Inc. a human touch. She started working at the original Apple factory scheduling the production lines for early Mac products like Macintosh SE and the Macintosh plus. She then helped build out the company’s very first retail and ecommerce sites, and then was instrumental in the company’s expansion across the globe. Now, as Senior Vice President of Retail + People reporting directly to Apple CEO Tim Cook, O’Brien is one of the highest-ranking executives at the company. “I just felt like the constant growth of the Apple culture is something that I tried to weave through everything that we did,” she tells InStyle. “So now, every day, I get to wake up and really think through how we make sure that we help support Apple employees to do the best work of their lives.”
O’Brien cites lessons she learned from Steve Jobs in those early days as the backbone of her people-focused philosophy. “Something that I think Steve really instilled in all of us is that technology is here solely to connect people,” she says. “Steve talked about Apple being at the intersection of technology and liberal arts, and that is how we all feel, that it's so much bigger than the technology itself.”
Retail Redux: Early this year, Cook tapped O’Brien to lead Apple’s retail arm in place of former Apple retail chief and former Burberry CEO Angela Ahrendts. Though some critics, who took issue with Ahrendts’s “town square” concept of nixing checkout desks back in 2017, say O’Brien has her work cut out for her to reenergize customers at Apple’s more than 500 stores across five continents and the company’s more than 70,000 retail employees, she remains undeterred by the wide scope of her task. In fact, she’s more enthusiastic than ever about her new role.
“First of all, I do have a lot of personal energy,” she says with a laugh. “And I feel like it is where all of the experience I've had at Apple comes together.” Since February, she has succeeded in opening and re-opening major retail storefronts including the iconic store on Fifth Avenue in Manhattan, which has nearly doubled in size and remains the only retail location in the world open 24 hours a day, every day of the year. Her Instagram is currently filled with photos of employees wide-eyed and smiling after meeting their new leader.
Recharging: O’Brien, a Michigan native, says she “bounces out of bed each morning” with unending optimism. “I love to start my day early. I get a lot of energy, first of all, from the outdoors,” she says, adding that living in California has made her love of being in nature an easy pastime to pursue. O’Brien also says that going through the tough times Apple’s faced throughout her tenure, like in the early 2000s around the time the dot-com bubble burst when Apple's earnings fell short of expectations, has actually taught her how to maintain her positivity. “Honestly at Apple, most people had written us off, they really didn't feel like we were going to make it through. But there's always hope. So, number one, I feel like I really learned a deep sense of optimism, but realistic optimism because you need to assess and have a great grounding in the realities of the situation you're in,” she says. “What I will tell you is those tough times at Apple, the only way we made it through was that we pulled together, and everybody played their part.”
Meaningful Mentorship: O’Brien credits her early mentors with pushing her to succeed beyond her expectations. “There are times where I wasn't certain I had the capability to perform a role that I was given,” she says. “But others had that confidence in me, and that really helped. That's something I really try and do now as a more senior leader is to help people see their potential.”
Most Badass Moment: When asked what the most badass thing she thinks she’s ever done, says coming out in her mid 20s about 25 years ago was one of her toughest and yet proudest moments. “I was scared, but knew I had to bring my full self to Apple,” she says. “I have never, ever regretted that big decision and today, I consider it my responsibility and a privilege to show up every day in support of our underrepresented team members. It is so important to me that everyone feels respected for who they are and that they have a deep sense of belonging.”
Best Advice: “I think, many times when people start their careers, they feel like there's got to be a very specific path. And, certainly I can tell you today, having worked 28 years in the supply chain at Apple and then now getting the chance to lead the people team and the retail team, I'm a good example of the fact that you don't know where your path is going to lead,” O’Brien says. Instead, she says she advises mentees to put the work in and be open to new opportunities. “If you continue to learn and focus on being a great team member, helping to support everybody you work with to do great work for whatever company you're working for, then you're going to have an incredibly fulfilling career because you're developing skills that will help you in every aspect of your career and your life.”
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