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.
Wes Kao is an executive coach, co-founder of Maven (the cohort-based learning platform backed by a16z and First Round), and co-creator of the altMBA with Seth Godin. She pioneered the cohort-based course category, scaled altMBA to 550 cities in 45 countries, and now helps senior tech operators at companies like Google, Amazon, and Shopify sharpen their executive communication and influence. Her biweekly newsletter reaches 300,000+ readers across platforms.
Dr. James Stanier is a computer science PhD turned engineering leader, author of three books on engineering management, and the mind behind The Engineering Manager newsletter with nearly 30,000 subscribers. He scaled Brandwatch's engineering team from startup to a $450M acquisition, led hundreds of engineers at Shopify, and now serves as CTO for the veterinary division at Nordhealth. His work distills what it actually takes to go from writing code to running organizations - without losing the technical edge.
Raylene Yung is an engineering leader, organizational designer, and public servant who scaled teams at Facebook and Stripe before co-founding U.S. Digital Response - the nonprofit that mobilized 10,000+ volunteers to help governments navigate COVID-19. She later served as Executive Director of the GSA's Technology Modernization Fund, overseeing $1B+ in federal tech investments, and as Chief of Staff at the Department of Energy's Office of Clean Energy Demonstrations. Now a board member at USDR and SolarAPP+, she writes 'raylene's field notes,' a Substack newsletter on climate, tech, and complex systems.
Roy Rapoport is a veteran engineering leader and writer whose work has quietly reshaped how tech companies think about people, reliability, and operational culture. Best known for his two stints at Netflix (where he built Insight Engineering and its operational platform) and a stint at Slack, Roy popularized the Manager README format and authored influential frameworks on feedback, trust, and performance improvement. He writes on Medium about the subtler mechanics of leadership, raises goats in California, and insists he will never retire.