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Joshua Winter

Director, Skills for Employability

Microsoft

Joshua Winter leads workforce development efforts on the Microsoft Philanthropies Skills and Employability portfolio. His work is focused on ensuring people unreached and displaced by technology are equipped with the computing and AI skills to be employed in the digital economy. Central to this work is creating a skills-based labor market in which life-long learning is valued. Throughout his career, Joshua has been driven by the pursuit of equity. Joshua has spent his career working in strategy development, program implementation and management in the workforce development and education sectors.

Most recently, Joshua led strategy for the New York City Department of Education creating its new theory of action to ensure all of the district’s 1,600 schools provide an equitable and excellent education to every one of its 1.1 million students. Prior to that, he implemented innovative workforce development initiatives at the New York City Economic Development Corporation, The Initiative for a Competitive Inner City in Boston, and at The Community Foundation for Greater New Haven.

Joshua began his career as a counterperson at Dunkin Donuts and later went on to join Teach for America as a middle school math teacher in the Bronx, NY. Joshua has served as a board member of The Workforce Development Corporation of New York City and was a founding board member of Camp Starfish, a non-profit camp dedicated to working with children with psychological and learning disabilities. He is a graduate of University of Vermont and holds an M.B.A from Boston University.

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