When Olof Mases talks to managers of companies that are being acquired by Microsoft, he tells them the story of his early career at tech startups in Sweden.
He explains that many of the employees at his 20-person startup were hired into Microsoft and how he was a little apprehensive about joining such a large, established company. “But Microsoft actually allows you to be very entrepreneurial,” he tells them, “There’s a lot of autonomy here and you can continue to build your career on your own terms.”
And Olof should know. Some eight years after starting at Microsoft, he has been a central figure in overseeing three startup acquisitions. In that time, he has also held four roles: Tester, Developer, Architect, and Program Manager (PM).
There are some other employees out there who’ve been Testers, Devs and PMs – known as “the Trifecta” – but Olof says, “I guess I went the extra mile with the Architect role.”
It is not that Olof gained this breadth of experience because he was crossing off titles from a bucket list. “Every job has been the right position for me at that time,” he says. “I’ve always felt that I’ve never been happier with my work than I am right now. And I can say that again now.”
He explains, “I am always looking for new challenges. That has led me down a route that has been super interesting and diverse. Microsoft has always provided me with engaging opportunities and I’ve simply pursued them.”
When Olof arrived at Microsoft, he had been the CTO at Stockholm-based startup. As the company split up, Microsoft hired out a number of their employees, including Olof.
He worked for his first year at Microsoft in Sweden, and then moved to Redmond. His team started hiring and soon quadrupled in size. “I was a PM and then was asked to head up the Dev and Test organizations,” he remembers.
Soon Olof tried his hand at bringing other companies into Microsoft. He was the Technical Lead in the acquisition of Cincinnati-based startup, Engiro. It was an exciting ride,” he smiles. “There are lots of interesting challenges like dealing with open source issues, all of the legal aspects, and acquiring code.” He was central to the acquisition of Opalis, a Canadian company, a year later.
After a run as an Architect for App Controller, Olof moved to Microsoft Silicon Valley to become the Dev Manager for the Mac Office team. “I had all of this non-Windows experience from my startup days but wanted to be on projects that were core to Microsoft,” says Olof. “Mac for Office gave me the chance to use my other skills and simultaneously work on the biggest product at Microsoft. It was ideal.”
Olof managed developers for what was to become Office for iPad. He worked on PowerPoint for iPad and Outlook for Mac. But, as Olof is Olof, he started looking for his next challenge. “I wanted to move back to PM again. It felt like the right role for me at that time. An opportunity opened up in Windows Server on Remote Desktop. It was a chance to come full-circle and work on some stuff that related to what I’d done at the very beginning on my career.” And now he is managing a new combined Engineering group of Dev and Test.
Olof’s relentless pace is driven by intellectual curiosity as much as entrepreneurial vigor. He recently gave a talk to some 80 new managers brought in through acquisition about life and career at Microsoft. He notes, “I’m not actually on the Venture Integration team. I just offer up my services when they’re needed. It’s something that I find really stimulating and fun.”