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From PCs to internet to cloud to AI: Jeff Alexander reflects on 35 years at Microsoft

Jeff Alexander loves to tinker. The 35-year Microsoft Australia veteran says he used to be called the ‘gadget guy’ and remembers pulling apart Compaq luggable computers to understand how they worked – and how he could do his job better.

This love for technology has seen him spend nearly four decades with Microsoft Australia, joining as an accounts payable clerk in 1987 when he was just 22 years old. He was the company’s 27th local employee.

Image of Jeff in the early 90s
Jeff Alexander joined Microsoft in 1987, and was Australia’s 27th employee (Source: Jeff Alexander)

“I didn’t know anything about computers,” he says. But he learned fast.

During that time, Jeff saw the growth of Microsoft and the full sweep of its evolution. This includes the move from operating systems that ran on BASIC, a programming language developed in the 60s, to more complex approaches and productivity applications, to a company-wide pivot towards the internet in the 90s. More recently, he’s witnessed the growing focus on cloud and artificial intelligence (AI). But he thinks the best is yet to come.

“Microsoft was an underdog back then, aggressively competing for market share,” says Jeff.

But we were always innovating and staying at the forefront of changes in the industry. And that’s how we got to where we are today.

Starting from the ground up

In the days before Windows 3.0, Microsoft was in fact, an Apple Macintosh shop. But when the new version of Windows arrived, staff quickly moved over, including Jeff, who had shifted from accounts into a customer service role.

“All of a sudden I had to learn how to use a PC,” he says. “And because we were such a small company there was no-one around to teach us. You had to figure it out for yourself.”

Staff were encouraged to get into the bits and bytes of any new product, play with it, break it and then learn how to get it fixed. The company was closely knit, and when stocktake time came, everyone turned up in old clothes, rolled up their sleeves and pitched in at the warehouse.

His increasing confidence and technical savvy soon saw Jeff move into technical support for the Word product. This was before the advent of screen sharing, so he’d sometimes spend up to 90 minutes on a call helping customers solve issues they were having with the software.

“The customer had to explain it to you, and you had to go ‘Okay, so this is the menu’ and so on over the phone. When I was in customer service, I was taking 150 calls a day, but in technical support it dropped to around 25 because of the in-depth nature of what we were doing.”

Embracing new experiences

One of Jeff’s career highlights was working as technical support for Microsoft co-founder Bill Gates when he toured Australia in the 1990s.

Photo with Jeff and Bill Gates
Pictured: Jeff Alexander with Bill Gates at his 20th anniversary dinner in Seattle in 2007

“When you’re a young person and someone comes from the mothership in Seattle, it’s really intimidating.”

The first question Gates asked him was how to get an external line at the hotel so he could download his email.

Later, Jeff moved into server management, a forerunner of the Azure cloud product, and then into a technical evangelist role, giving presentations at conferences and for user groups on Microsoft products.

“I couldn’t believe I was getting paid to travel the country and talk to people about tech and our products,” says Jeff. “I was just having so much fun.”

In his current job, he works directly with the engineering teams in Redmond on product feedback. Despite his wide job experience, Jeff says the best soft skill anyone can have is being able to present and connect with people. “It’s something you should teach everybody,” he says.

Staying curious

Microsoft has a very robust set of pathways for people wanting to move up in their careers, but Alexander says his passion for reading everything he could get his hands on has helped him shift from being someone who knew nothing about computers into complex technical roles.

With nearly four decades of service under his belt, Jeff attributes his longevity at the company to the flexibility, balance and incredible range of opportunities that Microsoft provides.

“It’s been an amazing journey for me. The company has grown so rapidly, and I’ve basically grown up with it,” says Jeff. “I met my wife at Microsoft in 1997, and in the 2000s I raised my young family.”

For young people at the beginning of their careers, his biggest piece of advice is to be patient.

“It takes time to build your career, and don’t be afraid of making mistakes and failing fast,” he says.

The industry is changing so rapidly, with AI set to transform everything. The role you’re in now will evolve, and it’s exciting to be part of that change.

“I want to keep what I have experienced alive for the next generation and inspire them to also have exciting and enriching careers in STEM.”