Diane Flynn

Chief Executive Officer

Diane builds what others think is impossible—especially when the challenge is funding or facilities. She began her career as a tax attorney structuring sophisticated financial solutions for businesses and high-net-worth individuals, expertise she now brings to mission-driven organizations. For more than two decades, she has applied her business acumen and deep understanding of capital to create durable solutions that strengthen nonprofit organizations and expand their long-term impact.

Diane has secured over $2 billion in financing for charter schools, enabling the growth of 20,000 seats. Prior to launching PSwrx, she led the real estate and financing strategy for KIPP NYC—the largest privately financed charter school facilities effort in New York City—advancing $640 million in financing and delivering more than 400,000 square feet for 3,400 students, consistently outperforming market benchmarks. 

From 2009 to 2018, Diane developed the strategy and led execution of Uncommon Schools’ real estate financing portfolio, guiding expansion from 17 to 52 schools and from 8 to 26 privately controlled facilities. Diane’s approaches resulted in regional facility costs that outperformed national norms by more than 10 percentage points, positioning each region in the Uncommon network for long-term financial and operational stability. 

Before taking roles inside Uncommon and  KIPPNYC, Diane led Two9Three Consulting, where she and her team delivered market-first solutions that strengthened clients’ financial and operational footing. 

Diane holds a B.A. from Villanova, a J.D. from Seton Hall, and an LL.M. in Taxation from NYU.