Phyllis R. Caldwell

Former President and CEO

Phyllis Caldwell is an advisor, corporate director, impact investor and former banker. She is managing member of Wroxton Civic Ventures LLC, an advisory services company she started in 2012. Since 2015, she has been on the Board of Directors of Ocwen Financial Corporation, serving as non-executive chair from March 2016 – January 2023. She is also on the boards of OneMain Financial, JBG SMITH Properties, Oaktree Specialty Lending Corporation and Chemonics International. She has served on the boards of several national and international nonprofit organizations engaged in housing, economic development, and food security, and is currently Vice Chair and Trustee of Enterprise Community Partners.

Previously, Phyllis spent twenty-five years in financial services in the private, government and not-for- profit sectors. She served as Chief of the U.S. Department of Treasury’s Homeownership Preservation Office overseeing foreclosure prevention programs established during the 2008 financial crisis. Before government service, she was President and Chief Executive Officer of Washington Area Women’s Foundation. Prior to that she spent over twenty years in commercial real estate and affordable housing finance and held a range of executive roles at Bank of America, including President of Community Development Banking.

Passionate about social enterprise, women’s philanthropy and entrepreneurship, Phyllis is an advisor and mentor to female entrepreneurs, and is an investor member of Portfolia, MEDA Angels and Citrine Angels. She also serves on the Leadership Council of Washington Area Women’s Foundation and is a founding member of Women of Color in Community Development.

She received her Master of Business Administration from the Robert H Smith School of Business at the University of Maryland, College Park and is currently an Executive-in-Residence at the Smith School. She holds a Bachelor of Arts in Sociology and Urban Planning, also from the University of Maryland.