Diana’s story is a testament to what can be achieved when compassion meets determination. Win doesn’t just fight poverty—it transforms lives.

Behind every family that finds a permanent home is an extraordinary team—maintenance workers, advocates, social workers, and drivers—who come together to make the impossible happen.

It’s not easy. With skyrocketing rents and a critical lack of affordable housing, the challenges feel insurmountable. Yet Diana’s leadership proves otherwise.

Whether it’s helping families navigate tedious housing applications, connecting them to childcare and income-building programs, or providing emergency support, Diana and her team work tirelessly to ensure every family has a pathway to stability.

“Families are coming to us with different needs, and we have to adapt to meet them where they are.”

Diana has seen poverty shift in ways few could imagine. Once middle-class families are now walking into shelter after a single job loss. “What we’re seeing is unprecedented,” she explains.

“Every day in shelter is another day of trauma,” Diana says, “and our job is to get families out, stabilize them, and make sure they never come back.”

As Chief Program Officer at Win @winnyc.bsky.social, Diana oversees a network of 16 shelters and supportive housing programs, helping move over 900 families out of shelter every year. She understands better than anyone the toll poverty takes on a family.

Diana Santos didn’t set out to spend nearly a decade fighting poverty in New York City, but her passion for helping families in crisis turned into a mission that has changed thousands of lives.