Shana Dall’Osto: Biography, Career and Roots and Wings Foundation

Shana Dall’Osto: The Philanthropic Leader Redefining Trust-Based Giving

Shana Dall’Osto is one of the most thoughtful voices in modern American philanthropy, known for leading the Roots and Wings Foundation with a model built on trust, humility, and genuine partnership with the nonprofits she funds. While her family’s connection to the multibillion dollar healthcare software company Epic Systems often draws initial attention, it is her own decades long career in nonprofit work, early childhood advocacy, and community service that defines who she really is. Shana Dall’Osto has become a respected name in philanthropic circles not because of inherited wealth alone, but because of how deliberately and humbly she has chosen to use it. This article takes a detailed look at the life, career, philosophy, and continuing impact of Shana Dall’Osto.

Who Is Shana Dall’Osto

Shana Dall’Osto Early Life and Family Background

Shana Dall’Osto grew up in Madison, Wisconsin, alongside two siblings, in a household that valued hard work and humility far more than material comfort. Her mother, Judy Faulkner, is the founder of Epic Systems, one of the largest healthcare technology companies in the world, but the family’s beginnings were far from privileged. Judy Faulkner was the second generation child of Ukrainian refugees and arrived at the University of Wisconsin-Madison on a full scholarship. Shana Dall’Osto’s father, Gordon Faulkner, worked as a pediatrician. Before their careers took shape, the couple lived in assisted housing and relied on food stamps to get by.

It was in 1979, the same year Shana was born, that Judy Faulkner started a small healthcare software company out of the family’s basement, originally named Human Services Computing. That company would eventually grow into Epic Systems, a global leader in electronic health records technology. Yet even as the company expanded and the family’s financial situation changed dramatically, the values instilled in Shana and her siblings did not. She has often reflected that the family was raised to be thrifty and grounded, a mindset that continues to shape her approach to giving today.

Shana attended Wingra School before moving on to Madison West High School, graduating with the class of 1997. She has spoken fondly of her time in Madison’s public school system, crediting it with instilling in her a love of learning and the ability to problem solve, qualities that would later become central to her professional life.

Education and Early Career of Shana Dall’Osto

After high school, Shana Dall’Osto pursued a bachelor’s degree in literature at Claremont McKenna College. Following graduation, she joined the Peace Corps, where she served as a teacher in Benin, West Africa. This experience marked the beginning of a long commitment to service oriented work and exposed her early on to the realities of community needs in under resourced settings.

After her time with the Peace Corps, Shana settled in Seattle, Washington, where she still lives today with her husband and their two children. In Seattle, she worked closely with populations experiencing homelessness, gaining firsthand insight into the systemic challenges many families face. She later spent seven years directing a children’s literacy program for low income families across Washington State, a role that deepened her passion for early childhood development and education. During this period, she also served as a Coordinator of Volunteers with AmeriCorps, where she focused on volunteer recruitment and training.

To formalize her growing expertise in early childhood leadership, Shana Dall’Osto later earned an Early Childhood Leadership Certificate from the University of Washington, along with a master’s degree in public administration. This combination of grassroots experience and academic training gave her a rare and valuable perspective, one that blends lived community work with strategic organizational thinking.

The Shift From Asking to Giving

In 2012, Shana Dall’Osto’s career took a significant turn. Her parents, recognizing her deep expertise in the nonprofit sector, asked her to help launch a new philanthropic initiative called the Magic Pebble Foundation. As she has described it, the foundation began modestly, with her working out of her own home while simultaneously raising young children. Each year, her parents would contribute funds, and the foundation would distribute them to organizations in need.

This period represented a meaningful shift in her career, moving from what she calls the asking side of nonprofit work to the giving side. It was a transition that required an entirely different skill set, one focused on identifying impactful organizations, building trust with grantees, and thinking strategically about long term community outcomes rather than day to day program delivery.

Founding and Leading Roots and Wings Foundation

Building on the foundation laid by Magic Pebble, the Faulkner family launched Roots and Wings Foundation in late 2019, with Shana Dall’Osto stepping into the role of Executive Director. The foundation was established with a clear mission, helping children grow strong from the roots up and supporting their full potential, symbolically represented by the idea of roots and wings.

Roots and Wings focuses its giving across four key areas, basic needs, early learning, safety and justice, and health. The foundation has grown substantially since its founding. Over its first five years, it quietly distributed approximately two hundred million dollars to three hundred and twenty different organizations focused on various aspects of early childhood development. Looking ahead, Shana Dall’Osto has estimated that the foundation will begin granting around one hundred million dollars annually to organizations across the country dedicated to the health, education, and overall wellbeing of children and families.

The foundation operates with a notably lean team, yet maintains strong relationships with more than three hundred grantee partners. According to organizational filings, Shana Dall’Osto serves as Executive Director on a full time basis, while her parents, Judith and Gordon Faulkner, hold the titles of President and Secretary respectively without taking compensation for those roles.

Shana Dall’Osto and the Trust-Based Philanthropy Model

Perhaps the most defining aspect of Shana Dall’Osto’s professional identity is her unwavering commitment to trust-based philanthropy. This approach to giving prioritizes flexibility, minimal bureaucratic hurdles, and genuine respect for the expertise of nonprofit organizations, rather than imposing rigid metrics and reporting requirements from the funder’s side.

When Roots and Wings officially launched, Shana and her team intentionally avoided being too rigid about mission statements or evaluation metrics, choosing instead to learn directly from the communities they served. This philosophy was put to an immediate test when the COVID-19 pandemic struck just months after the foundation’s launch. Rather than pausing operations to reassess, the foundation focused entirely on getting funds to organizations quickly and with as few conditions as possible.

Central to her trust-based approach is the belief that funders should do their own homework before approaching a potential grantee. This means using existing materials, such as annual reports, instead of demanding custom evaluations, and even assisting nonprofits in completing applications rather than placing the burden entirely on them. In some cases, the foundation has extended funding offers on the very first call with an organization, simply because the groundwork had already been done.

Shana Dall’Osto has also been clear that trust-based philanthropy is not in conflict with being strategic. She views it instead as a different kind of strategy, one that prioritizes equity, efficiency, and impact rooted in the real experiences of communities, rather than dictating exactly how, when, and what nonprofits should do with their funding. She has spoken openly about the resistance this model sometimes faces from more traditional funders who are hesitant to relinquish control, while also noting growing interest from a newer generation of philanthropists eager to adopt similar practices.

Recognition and Broader Influence

Shana Dall’Osto’s influence extends beyond her own foundation. She has been named a member of the UNICEF International Council, a global community of more than one hundred and seventy philanthropists and partners who contribute their resources and expertise toward solving urgent challenges facing children around the world. Roots and Wings Foundation has also become a long standing investor in UNICEF USA’s Every Child Fund, reinforcing the foundation’s commitment to childhood wellbeing on an international scale.

Closer to home, her connection to her own educational roots has come full circle. The Madison Public Schools Foundation announced that Shana Dall’Osto would serve as the organization’s next President, a role recognizing both her professional accomplishments and her continued connection to the community that shaped her early values.

Shana Dall’Osto Personal Life and Values

Despite her significant professional responsibilities, Shana Dall’Osto maintains a grounded personal life in the Pacific Northwest with her husband and two young children. She has spoken about the importance of family support, noting that raising children is wonderful but far from easy, and that families need as much support as possible to thrive. In her free time, she enjoys simple pleasures such as making pizza with friends and exploring the natural wilderness of Washington State. She has also mentioned playing ultimate frisbee year round, describing it as her happy place.

This grounded, family oriented lifestyle mirrors the values she brings to her professional work. Just as she prioritizes humility and genuine connection in her philanthropic relationships, she appears to apply the same principles to her personal life, valuing authenticity over status and community over individual achievement.

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Conclusion

Shana Dall’Osto represents a distinctive kind of philanthropic leadership, one shaped not by inherited privilege alone, but by years of direct community service, education, and a genuine belief in the power of trust. From teaching in the Peace Corps to directing literacy programs for underserved families, and eventually leading a foundation poised to distribute tens of millions of dollars annually, the journey of Shana Dall’Osto reflects a consistent thread of humility and purpose. As Roots and Wings continues to grow its impact across early learning, health, safety, and basic needs, Shana Dall’Osto’s voice within the trust-based philanthropy movement is likely to remain an influential one for years to come. Readers who want to keep up with more profiles, insights, and stories on leadership and philanthropy can continue exploring similar coverage on modernbytemedia.