Maya Winkelstein

Chief Executive Officer, Open Road Alliance

Maya Winkelstein is the CEO of Open Road Alliance, a hybrid philanthropic and investment initiative focused on advancing solutions to Keep Impact on Track. In her role, she is responsible for the organization’s overall strategy and management of the global Open Road Alliance team.

Since its inception in 2012, Open Road has made over $38million in grants and low-interest loans to organizations across the impact sector which have encountered unexpected roadblocks. Through this strategy, Open Road has kept over $411 million of impact on track across all sectors and geographies, for both registered nonprofits and for-profit social enterprises. The organization also conducts research and advocates for the adoption of long-term, system-wide risk management practices in the philanthropic sector.

Maya served as Open Road’s inaugural Executive Director, and previously worked as an Associate Director with the consulting firm williamsworks where her clients included the Eastern Congo Initiative, Nike Foundation, PATH, Tostan, and TOMS Shoes. Prior to williamsworks, she served in multiple roles across the nonprofit and government sectors focusing on program development, fundraising strategy, and corporate partnerships.

Maya writes and speaks frequently about Open Road’s work and its growing research expertise on ‘Risk Management in Philanthropy.’ She is a regular speaker at forums including the Council on Foundations, Grantmakers for Effective Organizations, Clinton Global Initiative, and PEAK Grantmaking. Her work has appeared in Stanford Social Innovation Review, Chronicle of Philanthropy, The Foundation Review and many other publications. In 2017, Maya was featured in the Chronicle of Philanthropy’s ‘On the Rise’ series and Huffington Post’s ‘Women in Business.’ She is a former Board Member of the Global Press Institute and a current member of the Leadership Advisory Council for

Maya holds a B.A. from the University of Michigan; MSc from the London School of Economics; and Certificate in Finance from Georgetown University.

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