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Abolade Gbadegesin at the Microsoft campus in Redmond, Wash. (GeekWire Photo / Nat Levy)

In 20 years at Microsoft, Abolade Gbadegesin has seen his share of major transitions.

He’s worked under all three of its CEOs — Bill Gates, briefly; then Steve Ballmer; and now Satya Nadella. Today, Gbadegesin is a distinguished engineer in the Windows Core Development group, but he was also integral in building the Windows Phone platform. He worked on the Windows Live Storage backend for OneDrive, led the design of cloud services for the file syncing program Live Mesh and oversaw the first major overhaul of the core networking technologies for Windows.

Gbadegesin now finds himself at the center of a sea change for the flagship Windows operating system as the company looks to adjust to an era in which it no longer dominates the larger world of computing. A major priority for Microsoft over the last year has been unifying the experience for users across Windows 10, Android and iOS, and Gbadegesin’s day-to-day work plays an important part in that.

This transition will surely continue at Microsoft Build, the company’s annual developer conference happening in Seattle next week. A year ago at Build, Gbadegesin was on stage to discuss Project Rome, a cloud-based set of tools that allows developers building third-party apps to break down the walls between devices.

Rome is a series of APIs and software development kits that are device and platform agnostic, focusing more on the big picture of how individuals use their devices. At its simplest level, Project Rome aims to alleviate productivity bottlenecks like users emailing files to themselves or employing USB sticks to transfer information. But users can also do other things like immediately pick up a movie where they left off through a push notification from Microsoft’s digital assistant Cortana.

“Think in terms of a meta operating system that is focused on you as a person as opposed to being siloed into individual devices,” Gbadegesin said.

Project Rome makes it easier to build experiences that transition well between devices. (Microsoft Photo)

Since Gbadegesin took the stage at Build a year ago to talk about the expansion of Project Rome, he has learned a lot. Microsoft expanded the focus from just the individual to also think about ways to simplify collaboration across devices. Gbadegesin called out a new feature being tested called Near Share that makes it easier to send files, URLs and other things wirelessly between nearby devices as an example of the next phase for Project Rome.

Gbadegesin won’t be back on stage at Microsoft Build this year. The three-day event next week in Seattle is expected to coincide with the birth of his second child.

From Nigeria to Harvard to Redmond

Like a lot of folks who have risen up the ranks at the Microsoft mothership in Redmond, Wash., his is a global experience. He was born in Nigeria. He started kindergarten in the U.S. before returning to Nigeria, and later came back for high school. After graduating from Harvard University with a bachelor’s degree in computer science, he joined Microsoft straight out of school and has been there ever since.

He started in 1998 but interned previously in 1994, a time before some of Microsoft’s newest workers were even born, lured by the promise of working on Windows.

“At the time I really wanted to work on operating systems, and there weren’t that many places in the world where you could do that,” Gbadegesin said. “And I was in love with the architecture of Windows NT.”

Microsoft’s Abolade Gbadegesin at Microsoft Build 2017. (GeekWire Photo / Kevin Lisota)

Having worked at Microsoft for so long, Gbadegesin has picked up quite a few titles along the way. One of the most important is his role as technical advisor to Terry Myerson, the Windows chief who is leaving the company as part of the recent reorganization of Microsoft’s engineering teams.

That job may sound like something of a personal IT guy, but it’s a lot more than that. Gbadegesin as technical advisor helps shape Windows’ long-term agenda. In that position he works closely with Gates, has been serving as a part-time technology adviser at the company since 2014, when Nadella succeeded Ballmer as CEO.

Gbadegesin didn’t get specific about the Windows roadmap, but he said in general, the operating system will be infused with some of the futuristic concepts that today are the focus of the company’s research divisions: machine learning, natural language processing and computer vision, as well as a continued focus on reimagining how Windows works across devices.

Myerson bestowed upon Gbadegesin another title, this one more Game of Thrones than Microsoft: “fixer of things that are broken.” Great engineering teams, Myerson would say, have a combination of “painters and plumbers.” The painters are the people who think about the look and feel of the product: what the user wants, what it should look like. And then there are the folks that make sure things work and fix them when they don’t. Gbadegesin is one of those.

“You need plumbers, people who get into the guts of the building and can rip stuff apart, put it back together again, change the way the building works, fix things that are broken,” Gbadegesin said. “And he puts me in that category a fixer of things that are broken. It basically means you want to make major changes to Windows, or when we have major challenges as a result of technology shifts, I tend to get involved.”

An uncertain new era for Windows

Gbadegesin didn’t want to talk about the reorganization or how Myerson’s departure affects him. The reorganization shuffled the deck among Microsoft’s engineering groups, emphasizing growth areas like cloud computing, artificial intelligence and its suite of productivity tools. Those changes come somewhat at the expense of Windows, which is being split across multiple groups.

Microsoft insists that Windows remains an important part of the company and plays a crucial role in its cloud business and Microsoft 365, a combination offering of Windows 10, Office 365 and the Enterprise Mobility + Security Suite.

Microsoft has always been a company that is quick to pivot, but that is a feature not a bug of the new culture under Nadella, Gbadegesin says. He particularly enjoys the emphasis on learning along the way, captured in Nadella-speak that Microsoft wants to have a “learn-it-all” culture, rather than a know-it-all culture.

“Satya talks a lot about (Microsoft) being a learning culture, and that’s great just for an aspect of humility and not necessarily thinking I know how people are going to respond to something. If you look at how we’ve rolled out features, that’s actually an example where we’re saying we’re not sure, we think there’s something here, and we’d like to hear from the community and get that feedback, iterate and build it in the open together with the folks who are going to be taking advantage of it.”

Gbadegesin can be bit of a tough nut to crack. He’s clearly enthusiastic about the work he’s doing at the company, but it’s more of a quiet excitement than a loud, Ballmer-esque bluster, and he demurred on a few topics. His demeanor during our interview in a conference room at Microsoft Studio F, where his office is located, doesn’t deviate much from when he got on stage last year to talk about Project Rome at Microsoft Build. That day last year he wore a beige hoodie with blue jeans, and for our meeting he’s donned a blue hoodie with jeans.

Laura Butler, corporate vice president of OneNote for Microsoft. (Microsoft Photo)

But don’t let the calm demeanor fool you, says Laura Butler, Microsoft’s corporate vice president of OneNote and a technical fellow focused on notes and tasks.

“Just because he’s not somebody who’s like ‘aaaahhhh everything’s on fire’ all the time, that does not mean he is not super sharp,” Butler said. “Your average Wall Street stereotype I think would find his wallet missing after having a seemingly calm conversation with Abolade.”

Butler’s relationship with Gbadegesin dates back to when they were both on the Windows Phone team together in 2010 and promoted at the same time. She called Gbadegesin one of her “favorite human beings” and described him as a visionary.

That calm personality helps him work through problems without a lot of stress that you might see from the Type A types. He’s a great listener, she says, who can cut to the heart of problems quickly. He fights for quality and and refuses to cut corners.

Butler said If Gbadegesin ever gets tired of Windows, she’d love to have his “enormous brain and other skills” on her team. Butler added that it doesn’t get talked about enough, the need for good, reliable people in tech and Gbadegesin is exactly that, she said.

“Abolade is a good human being,” she said. “He’s somebody that if you were in a tough situation, and maybe there wasn’t enough food, like maybe the Walking Dead and the zombies, you’d want at your side.”

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