Joshua Winter

Joshua Winter is an accomplished nonprofit and social impact leader with more than two decades of experience driving organizational growth, strategic transformation, and workforce innovation across sectors. As Chief Operating Officer of Upwardly Global, Joshua led a $25M national organization through a successful scale-up strategy that quintupled its impact, helping 25,000 immigrant and refugee professionals annually achieve meaningful employment. Previously, as Regional Senior Vice President at Per Scholas, he guided multi-site expansion across the West, strengthening programs that prepare individuals historically excluded from the digital economy.

Earlier in his career, Joshua launched Microsoft Philanthropies’ global Career Pathways initiative, advancing digital skills and inclusive hiring for tens of thousands worldwide, and led major strategic and operational reforms for the New York City Department of Education and Economic Development Corporation, delivering measurable improvements in performance, efficiency, and community outcomes.

Joshua brings deep expertise in strategy, turnaround management, and partnership development, grounded in a commitment to equity and systems change. He holds an MBA from Boston University and a BA from the University of Vermont.