I Have the Best Job at Park

I have the best job at Park. As Director of Development, my role requires connection across the entire community in a way few others do. I partner with trustees and grandparents, first-year parents and graduating families, faculty and alumni from every era of Park’s history. I attend student performances and push PreKers on swings. I sit with alumni in their homes and hear their stories. I invite families to advance our institutional priorities with transformational investments. I celebrate my colleagues and nurture our employee culture. Few positions at Park allow one to move so fluidly across generations and experiences. That vantage point is a gift I treasure.

Over my years in advancement, I have learned that fundraising success is never simply about strategy or scale – it is about culture. At Park, our culture of philanthropy is rooted in connection. We practice inclusive fundraising, centered in community. We believe that each gift represents a personal story, a belief in the mission, and a desire to contribute to something larger than oneself. We celebrate collective impact. No single gift defines us; it is the breadth of participation that signals our strength. When hundreds of families give in ways that are personally meaningful to them, it reflects trust and shared purpose. 

We believe that each gift represents a personal story, a belief in the mission, and a desire to contribute to something larger than oneself. We celebrate collective impact.

This relational approach is especially important as we navigate generational shifts in donor behavior. We know Millennials are values-driven and impact-oriented with their philanthropy. They expect transparency and authenticity. They are inspired less by tradition and more by connection and clarity of purpose. Park’s highly personal approach – one rooted in conversation, partnership, and gratitude – meets this moment. It ensures that as new generations of families begin their Park journey, they experience philanthropy not as an obligation, but as an invitation. And when we get this right, generosity becomes an expression of belonging. When a family makes their first gift, when a grandparent honors graduation with a special gift, or when alumni reconnect in support of the School, they are saying, “We are part of this.”

That is why Giving Day on March 5 matters so much. It is not just a 24-hour (ok, ok, it stretches a bit longer than 24 hours) fundraising event. It is a visible expression of community alignment – an opportunity for every family, alum, and friend to Leave Your Mark on Park.

So I really do have the best job at Park. I am entrusted with stewarding not only resources, but relationships. And every day – especially on Giving Day – I see what is possible when a community chooses to invest in itself.

-- Shannon O'Leary, Director of Development