Agents of Impact | April 15, 2022

Maya Winkelstein, Open Road Alliance: Helping social enterprises through life’s ‘OMG’ moments

Amy Cortese
ImpactAlpha Editor

Amy Cortese

If it feels like one calamity after another, put yourself in Maya Winkelstein’s shoes.

Open Road Alliance, which Winkelstein has led for a decade, steps in with financing to bridge social enterprises through “unexpected OMG moments.” The setbacks range from the mundane (bureaucratic delays) to the momentous (Brexit, Covid, Ukraine).

Over 10 years, Open Road has kept at least $800 million worth of impact on track with more than $70 million in grants and short-term bridge loans to more than 300 social impact organizations.

Winkelstein helped shape the strategy as a consultant to philanthropist Laurie Michaels, who wanted to help social impact groups get “unstuck.” When the two-year consulting gig was up, Michaels tapped Winkelstein to run Open Road. 

Now, Winkelstein is handing over the reins to longtime deputy Caroline Bressan, a veteran of Calvert Impact Capital and Dalberg Advisors.

Bressan spearheaded Open Road’s move into lending and launched its first fund. Her goal: 10X Open Road’s lending. “This is a billion-dollar market annually in bridge loans, and we’re hoping to step up and fill as much of that gap as we can,” says Bressan, who joined last month’s Agents of Impact Call on political risk.

Winkelstein will stay on as an advisor. “Building Open Road has been the dream job of a lifetime,” says Winkelstein. With Michaels, she’s cooking up a new project to address climate impacts in Louisiana. “So I’m not going too far outside of the Open Road family.”