Future-Proof Your Career – This Veteran From Apple Reveals How

With a career spanning over 30 years with tech giant Apple, Deirdre O’Brien shares some sage advice every working woman should know.

Dierdre O'Brien and Tim Cook greet employees at an Apple store in the US.
Dierdre O'Brien and Tim Cook greet employees at an Apple store in the US.
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She may have been at Apple for 30 years, but for Deirdre O'Brien, the fun is just getting started. The Senior Vice President of People and Retail at the world's biggest tech company, Deirdre has been a quiet player in Apple's operations since she joined in 1988 after graduating from university. Now, three decades on, that's about to change.

Life Lessons

Having previously kept a low profile despite her high-ranking position, Deirdre joined Instagram under the username @deirdre.at.apple in April 2019, and in that time, has amassed nearly 40,000 followers who want to be kept up to date about what's happening at the company.

“It hasn’t felt like 30 years at all,” exclaims Deirdre, aged 53, when asked about her tenure at Apple. “Looking at my career, what made me stay, was the learning opportunities. I’m always learning. Apple is a great place to continuously learn and be creative.”

The drive to ingest and innovate has served Deirdre well as she rose through the ranks to become Senior Vice President of People in 2017, overseeing staff over a hundred thousand-strong. She then took on an additional role as the Head of Retail earlier this year – an ideal fit for someone who was part of the team that launched Apple’s very first online and retail stores.

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Connecting People

“People are at the heart of everything we do at Apple and our people are what drive the retail business. People come to Apple to do the best work of their lives, and you can see that passion in our retail teams especially, wherever they are in the world,” shares Deirdre.

Managing some 150,000 people across multiple regions from the US to right here in Singapore is no easy feat, however, but Deirdre takes the challenge in her stride.

“Communication and collaboration are essential when you’re overseeing an employee pool of that size,” explains the Apple veteran. “Jumping on a plane and meeting people face to face is something that I try to do often, but creating an environment that’s inclusive and diverse is also important to me. When people feel included and part of a diverse team, they come into work feeling their best self and when you feel your best self you do your greatest work.”

Making An Impact

Apple has always been known to stay ahead of the curve, producing products that are among some of the most coveted on Earth. But in a retail landscape that is looking gloomy, even the tech behemoth, is facing challenges. Deirdre, however, isn’t fazed.

“What we’re doing with retail is enriching the customer whether it be through the ‘Today at Apple’ sessions where Singaporean children can learn coding, or through interaction with our employees who can offer people a hands-on experience with our products,” says Deirdre. “It’s all about preparing them for a future where technology is empowering.”

Speaking of the future, Deirdre has a wealth of experience on how to future-proof your career in an ever-evolving work landscape:

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