Maya Winkelstein // CEO of Open Road Alliance

Investing in Impact | Impact Investing

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In episode 30 of the Investing in Impact podcast, we speak with Maya Winkelstein, CEO of Open Road Alliance on using a hybrid philanthropic model to make over $50 million in grants and low-interest loans to organizations and companies across the impact sector.

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 $50 million 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 Grantmakers for Effective Organizations, Skoll World Forum, 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 GrantAdvisors.org.

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

About Open Road Alliance

Our loans help social enterprises and nonprofits overcome obstacles to impact as they challenge the status quo to create a better world.

From the tele-health company requiring additional equipment and staff due to rapid demand during COVID-19, to the social enterprise facing a delayed Series A investment due to Brexit, Open Road loans ensure innovative efforts to address the world’s greatest challenges can carry on without interruption.

Our investment strategy is designed to keep impact first. We seek to maximize social returns while meeting financial requirements. We exist to serve the social sector, not the other way around. If you think that you are eligible for a one-time Open Road loan please submit an initial inquiry.

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