From drying silverware at his family’s Boston restaurant to becoming Microsoft’s Chief Marketing Officer, Chris Capossela’s journey is a masterclass in humility, hustle, and heart. In this episode of Microsoft Alumni Voices, Chris reflects on his 32-year Microsoft career—from driving a U-Haul across the U.S. to demo Office, to working alongside Bill Gates, to helping shape the company’s cultural and cloud transformation under Satya Nadella. Hear how a waiter’s instinct to read the room became a leadership superpower, and why Chris believes the best legacy isn’t a name on a product, but the people you help rise.
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From a dart thrown at a map to a decades-long career shaping the future of computing—Jon DeVaan's journey is anything but ordinary. In this compelling episode of Microsoft Alumni Voices, Jon reflects on his 29-year Microsoft career, from debugging early versions of Excel to leading engineering excellence across Windows and Office. Hear how a math major from Oregon State helped pioneer the daily build, championed collaborative leadership, and navigated the chaos of Longhorn and the vision of Windows 8. Jon shares what it means to build not just great software, but great teams.
Photo courtesy of Microsoft Alumni Network
