Deirdre O’Brien’s official title at Apple is senior vice president of what is an immense responsibility.
“We’re up to approximately 170,000 employees here at Apple, and that’s everything from finding the best talent to really supporting our team’s development, and all of the things that go around that,” O’Brien says.
It sounds like her job is more than enough to keep her busy every minute of every day, but then she nonchalantly adds: “I’m also the leader of the Apple retail team, and we have stores all over the world, and an online store that serves even more customers than our physical stores.”
The size and value of major corporations are appraised by various organizations using different metrics, but all of them essentially agree that Apple’s market cap now exceeds a remarkable $4 trillion.
O’Brien’s journey to a top position at one of the most valuable companies in the world began in the early 1970s in a Detroit suburb that bills itself as “The City of Tomorrow, Today.”
“I grew up on Mill Pond Drive in Troy,” she says. “My dad worked for General Motors, and my mom worked in the lab for 30 years at Troy Beaumont Hospital (now Corewell Health Beaumont Troy Hospital).
“We had a fantastic neighborhood, with people who worked in all sorts of different walks of life. But I don’t think there was anybody who didn’t do something related to the auto industry, or some sort of shop work.”
full-service retailer opened on Sept. 19, 2025. // Courtesy of Apple
O’Brien’s fond recollections include her education at various schools in Troy, including Hill Elementary School, Larson Middle School, and Troy Athens High School.
“What I loved was everybody just wanted you to be your best, and it was a very supportive environment,” she says. “When I think back to my time in school, there was not only the encouragement with academics, but also with athletics.
“And for me, in addition to a good education, I feel so grateful for the sports I was able to play and the teammates I had. I played soccer, basketball, volleyball, and golf, and I learned so much from those experiences, as well as (gaining) skills as a teammate and helping the whole team.”
When O’Brien began her college education at Michigan State University in East Lansing, she wasn’t sure what curriculum to pursue.
“I thought I wanted to be a business major, maybe an engineer. I wasn’t really certain,” she says. “But just a few years before I went to Michigan State, they had the very early beginnings of a unique program for an operations degree.
“It’s now called supply chain, and I decided to check it out. I fell in love with it from day one. It was about how you can take things that can be very complex and disjointed, and find a way to line them up. It really connected with me because it had a mathematic component and a process component to help companies drive great customer satisfaction — and the customer is always at the end of every supply chain.”
As O’Brien pursued her bachelor’s degree, she spent her summers back home at Sylvan Glen, a local golf course where she learned to schedule tee times, worked in the pro shop, and served as a course ranger.
Then, she says, “When it was time for me to start interviewing and get a real job, there were companies that came to the Michigan State campus to interview the students, and Apple had this great group of very young, vibrant people wearing jeans, not business suits.
“Their love for what Apple was creating immediately resonated with me, and all I thought about was I really wanted to get a job at Apple.”
The dream came true in 1988, soon after O’Brien graduated from Michigan State, when she launched her career as a production planner at the technology company.
She initially was part of the team that made sure the final manufacturing process went smoothly for various models of the Macintosh computer (Mac and the Mac SE).
She also began working her way toward completing an MBA at San José State University through a special program tailored for Apple, and sponsored by Apple University.
Now closing in on 40 years with the company, O’Brien has experienced a mercurial rise through the ranks, reaching the pinnacle of executive positions — but her attitude about any job she’s ever held at the company has never wavered.
“To be pushing yourself to do more and to do better with a group of people is an incredibly fulfilling thing,” she says. “I felt that way from my earliest days, being part of sports teams and working on school projects.
“I took that through to Michigan State. From day one, I’ve honestly felt it’s so important to have a purpose to give meaning to your life, and work hard, and do things that perhaps you thought you couldn’t even accomplish.”
O’Brien’s go-for-it attitude explains why she’s been a vital participant in virtually every significant Apple milestone over the years.
She helped create the Apple Stores and launched Apple’s first combined online and retail stores, and she was involved with the release and support of every major product the company has produced in the past 20 years.
Her pathway included direct contact with the late Apple co-founder, Steve Jobs.
“I have to tell you, every person at Apple was completely blown away by what an incredible person he was, in the shortest window of time, so I can’t say enough about Steve,” she says.
“Any of us who worked at Apple while he was here were touched by him in one way or another. Every time I got to be around him, I was always in awe of his intellect, his curiosity, and his drive for excellence. He was a truly unique individual, and I feel like his DNA lives so much in this company today.”
No more so than in the iPhone, arguably Jobs’ most significant achievement when it was introduced in the summer of 2007.
“I was very fortunate to get a chance to work on that product, and it has been incredible to see what’s become of it,” O’Brien says. “I don’t think any one of us ever had any idea how much the iPhone was going to transform Apple, and also our customers’ lives. When I opened up the first box with the final product, it felt like a game-changer.”
With all O’Brien has experienced and accomplished during her tenure at Apple, it’s no wonder her colleagues express a sense of awe when her name comes up.
“Given what Deirdre does today, I’m a little surprised one of those childhood sports wasn’t juggling plates and knives,” says Greg “Joz” Joswiak, Apple’s senior vice president of worldwide marketing. “It’s truly remarkable to watch her manage what are essentially two full-time executive roles. Retail is one of the most visible and personal expressions of Apple in the world.
“It’s where millions and millions of customers come to discover our products, get help, learn something new, or have a problem solved. And the people team touches every part of Apple, helping support and develop the teams that make all of it possible.
“Either one of those roles would be enormous on its own. Together, they require extraordinary judgment, stamina, empathy, and operational excellence. And Deirdre somehow makes it look natural.”
Joswiak should know. He recently celebrated his 40th anniversary as an Apple employee.
“I started at Apple (about two years) before Deirdre, and we’re (almost) in our fourth decade of working together across a variety of roles,” he says.
“What I admire most is that she never lets the scale of the work distance her from the people at the center of it. She listens, she seeks input, she stays grounded, and she brings a calm, steady confidence to incredibly complex decisions.
“That’s a rare kind of leadership, and Deirdre does it with real grace. I’m sure sports helped shape that, but there’s also something very innate about her leadership. She has extraordinary capacity, great judgment, and a level of humility that makes people want to follow her.”
As it turns out, the pair’s lengthy careers at Apple aren’t the only thing Joswiak and O’Brien have in common.
“I grew up in St. Clair Shores, just a stone’s throw away from Detroit,” says Joswiak, who earned an engineering degree at the University of Michigan in Ann Arbor. “I think we share that Michigan grounding of being practical, hard-working, team-oriented, and focused on building things that matter.”
Speaking of those Michigan roots, a highlight for O’Brien occurred last fall when she was on hand for the official debut of the Apple Store along Woodward Avenue in downtown Detroit.
“It was one of my proudest moments ever at Apple to be there for that opening,” O’Brien says. “For those of us who grew up in Michigan and are of our generation, Detroit was one of the most vibrant, strongest, and most productive business centers in the United States, and that’s what it felt like when I was growing up there.
“It was incredible, full of promise, full of opportunity, and now we have a developer academy and a manufacturing academy there (in the central business district),” she says proudly.
“I can’t tell you how thrilled I am to see where Detroit is today, with so many strong, innovative, and capable people who can create the future, and it’s been really great to witness from afar.”
O’Brien’s connections to her hometown go far deeper.
“My best friends in the world live in Michigan,” she says, “and I still talk and connect with my college roommates every single day. My brother still lives in Troy, and my nephew just got accepted to Michigan State, which I’m thrilled about. They’ve all been a really wonderful force for me, to have such a strong connection and base that grows from Michigan.”
But O’Brien readily concedes her job takes up most of her time, and those summer days hanging out at the golf course are long gone.
“Golf fell by the wayside my first year at Apple in California; it was way too time-consuming,” she reveals. “Now, I devote my free time to hiking and running on the beautiful trails in the Bay Area.
“I work at Apple 24/7, and fortunately for me I think I found the best home I could ever find in my career here at Apple. We want to make a positive impact on the world, so we’re always pushing the bar, and that takes real work. You don’t just talk about it; you’ve got to do it.”
“I CAN’T TELL YOU HOW THRILLED I AM TO SEE WHERE DETROIT IS TODAY, WITH SO MANY STRONG, INNOVATIVE, AND CAPABLE PEOPLE …”
— DEIRDRE O’BRIEN
