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Alumni: Shana Dall’Osto

Making a Direct Impact on Other Families Who Need It Most

Madison West High School class of 1997 alumna Shana Dall’Osto is the executive director of Roots & Wings, a family foundation created in late 2019 with a special interest in funding nonprofits across four key categories: family safety, health, early learning, and basic needs. For Dall’Osto, it’s her dream job. Not only is the family behind Roots & Wings her very own – her mom is Judy Faulkner, founder of the Verona-based, multibillion-dollar health tech software company Epic Systems – but Dall’Osto also has an extensive background in nonprofits, and a passion for service work focused on early childhood.

Growing Up in Madison

Dall’Osto and her two siblings were raised in Madison. “I did not grow up with great wealth,” Dall’Osto says—nor did her parents. Her mom, a second-generation child of Ukrainian refugees, arrived at the University of Wisconsin–Madison on a full scholarship. So did her dad, pediatrician Gordon Faulkner. They lived in assisted housing and used food stamps before building careers and starting a family. It wasn’t until 1979, the same year Dall’Osto was born, that Judy Faulkner started a healthcare software company (originally called Human Services Computing) in their basement. The company later became Epic Systems Corp and grew at a steady pace over the years. But even as Epic grew (and along with it, the family’s wealth), the Faulkners remained grounded in their roots. “We were raised to be somewhat thrifty,” Dall’Osto reflects.

With her family residing on the southwest side, Dall’Osto attended Wingra School and West High. As Dall’Osto reflects on her time in Madison’s public schools and what impacted her most, she comments: “It was really a love of learning and the ability to problem solve. Those two things have served me well my whole life – in the classroom and beyond.”

A Passion for Service Work  

After graduating with a bachelor’s in literature from Claremont McKenna College, Dall’Osto joined the Peace Corps serving as a teacher in Benin, West Africa. She then settled in Seattle, Washington where she still lives with her husband and their two young children.  

Professionally, Dall’Osto worked with formerly- and currently- unhoused populations, then spent seven years directing a children’s literacy program for low-income families across Washington State. In 2012 Dall’Osto shifted gears and moved from the “asking side” to the “giving side” when her parents sought her expertise for the launch of a new fund, The Magic Pebble Foundation.  

“The Magic Pebble Foundation was just me working out of my house at the same time I was raising little kids,” Dall’Osto says. Every year her parents would put in some funds and then the Foundation would distribute them. By 2019, almost 100 Dane County nonprofits had received grants from the Faulkners, though most were unaware of the origin of those funds. The Magic Pebble website did not mention Epic or the Faulkners by name, and with Dall’Osto using her married name, the source of support was shrouded.  

In 2015, Dall’Osto’s mother signed The Giving Pledge, beginning a transition toward greater giving and a more strategic philanthropic approach. “My goal in pledging 99% of my assets to philanthropy is to help others with roots – food, warmth, shelter, healthcare, education – so they, too, can have wings,” Judy Faulkner wrote. Out of that commitment, the Roots & Wings Foundation was launched in 2019 – and once again, under the leadership of Dall’Osto.

Still Rooted in Wisconsin 

Headquartered in Dall’Osto’s chosen hometown of Seattle, Roots & Wings makes grants nationally, with a particular focus on Wisconsin, Washington, and Oregon, where the Faulkners and their family reside. Roots & Wings funds nonprofit organizations that help low-income children and families reach their full potential through prevention, early intervention, and in-depth programming that changes lives.  

Roots & Wings supports both direct services and advocacy and takes a trust-based approach to grantmaking. “Our goal is to take the burden off nonprofits. That means doing the research ourselves and having a conversation with a potential grantee as a starting point, so once we ask them to submit the paperwork, there’s good alignment already and we’re not wasting anyone’s time,” Dall’Osto said. Regarding this somewhat unconventional approach, Dall’Osto comments: “I have to give credit to Judy, because she not only has a higher risk tolerance, maybe, but also a trust that nonprofits are doing good work. This is a belief I share as well — that the folks who are closest to the work know the work best. They know it better than us as funders. And they are overworked and under-resourced.”  

In 2022 Roots & Wings made $40 million in grants to more than 240 different organizations, spanning the fields of basic needs, early learning, family safety, and health. To give back to the community where the Faulkners have lived and worked, 85 of these organizations are based in and around Madison – two of those organizations being our very own Madison Public Schools Foundation (MPSF) and Madison Metropolitan School District (MMSD). To date, MPSF and MMSD have been granted more than $1.6 million in combined funding for MPSF’s operations, and MMSD’s birth through three programs, 4K program, and mental health supports.

“Over the last few years, the Foundation has launched new programs to increase the impact we have and the resources we deliver to Madison public schools,” commented MPSF President Melinda Heinritz. “Support from Roots & Wings has been a critical factor to our ability to innovate and sustain new ways to benefit MMSD students, staff, schools, and families. We wouldn’t be where we’re at in 2023 without the trust-based philanthropy practiced by the Roots & Wings Foundation.”  

In addition to making a direct impact on other families who need it most, Dall’Osto is also busy nurturing a family of her own. “Raising kids is wonderful, but it’s not easy. That’s why all families need as much support as possible,” she explained. “When our family has free time, we like making pizza with friends or exploring Washington State’s wilderness. I also play ultimate frisbee year-round; it’s my happy place!”   

Madison’s public schools are proud to count Shana Dall’Osto among their alumni! 

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