Joshua Winter

Chief Operating Officer

About Joshua Winter

As Chief Operating Officer, Joshua supports Upwardly Global’s ability to deepen impact and drive programs tailored to support immigrant and refugee mobility and visibility within the U.S. hiring system. He has over 20 years of experience in strategy development and program implementation.

Prior to joining Upwardly Global, Joshua served as the Western Regional Senior Vice President at Per Scholas, an organization that advances economic equity through rigorous training for tech careers and connecting skilled talent to leading businesses At Per Scholas, Joshua oversaw operations across five regions and supported Per Scholas’s expansion to additional sites.

Joshua previously served as Microsoft’s Director of Skills for Employability, where he connected underrepresented communities in the tech sector with skilling opportunities and employer-matching programs for gainful employment. In the past, he has also worked in policy and strategy roles, including at New York City’s Department of Education, NYC’s Economic Development Corporation, and the NYC Department of Transportation.

Joshua began his career as a middle school teacher through Teach For America before transitioning to philanthropic and community-focused work with the Initiative for a Competitive Inner City and The Community Foundation for Greater New Haven. He graduated from the University of Vermont with a B.A. in applied mathematics and Spanish literature and later earned his Master’s in Business Administration from Boston University.




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