windows
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Microsoft Won by Learning to Stop Being Windows
For years, Microsoft treated Windows as the answer. Its second act began when it made Windows merely one answer - and turned the rest of the company into a machine for selling picks and shovels to everyone.
James Howell
James Howell is VP of Windows Marketing at Microsoft, leading the company's push to define the AI PC era. Based in Woodinville, Washington, he has been at the forefront of marketing Copilot+ PCs and positioning Windows 11 as the platform for on-device AI. He has been a key Microsoft spokesperson on the AI PC transition, championing Copilot+ as a new hardware category and appearing in press and video series including 'Innovators Powered by Best Buy' to evangelize what AI can do for everyday PC users.
Stefan Kinnestrand
Stefan Kinnestrand is Vice President of Product Marketing at Microsoft, where he leads go-to-market strategy for cloud endpoints and commercial end user computing - spanning Windows Commercial Client, Windows 365, Azure Virtual Desktop, Cloud & AI Devices, and Microsoft Intune. A 23-year Microsoft veteran originally from Stockholm, Sweden, he has built a track record of transforming products from incubation to billion-dollar businesses and driving multiple-billion-dollar incremental revenue for Microsoft and its partners.
Wispr Flow
Wispr Flow is a San Francisco-based AI voice dictation platform that converts natural speech into polished, formatted text across any application at roughly 220 words per minute - about 4x faster than typing. Built by two Stanford AI researchers, the company has quietly become the voice layer that 270 Fortune 500 companies rely on, combining a 10% word error rate (vs. 27% for OpenAI Whisper), 100+ language support, and context-aware formatting that automatically adjusts tone and style based on the active app. With $81M raised and a $700M valuation as of late 2025, Wispr Flow is racing to become the default voice-first operating system for a billion users.
Steven Sinofsky
Steven Sinofsky spent 23 years at Microsoft building some of the most-used software in history - Office, Windows 7, Windows 8, and secretly, the Surface tablet. A meticulous operator who refused to promise features until they were ready, he rose to become President of the Windows Division and Microsoft's most likely successor to Steve Ballmer before his abrupt departure in 2012. Today he's a Board Partner at Andreessen Horowitz (a16z) and writes Hardcore Software, a serialized Substack memoir chronicling the rise and fall of the PC revolution from the inside.