Sylvia Watts McKinney is a dynamic change agent who is committed to innovative programs and services that lift children and families out of poverty. She uses a range of adaptive and technological management strategies to solve complex problems and get positive results. She is a successful entrepreneur and has held senior management positions at a number of nonprofit organizations.

Sylvia is a mission-driven and creative leader recognized nationally for her innovations in real estate, nonprofit governance/operations and entrepreneurship. She is adept at driving change and instilling a culture of collaboration. She has special interests in urban and ecosystems planning, youth education and leadership development.

Sylvia started her real estate career with a start-up company, Taylor Properties, where she successfully negotiated and finalized construction, permanent and equity loans with private banks and government agencies to build and sell affordable, fee simple housing, as well as commercial properties. She later assumed the role of Chief of Staff at the Massachusetts Executive Office of Transportation and Construction.

As Executive Director of the Museum of Afro American History, the Network for Teaching Entrepreneurship and Summer Search Philadelphia, she provided leadership on key strategic plans and implemented fundraising programs with staff and stakeholders. In addition, she collaborated with the members of the media to promote the missions of these organizations, resulting in various articles, live television coverage and the creation of videos and films.

Drawing upon her experiences in both the private and public sectors, Sylvia joined Thompson Island Outward Bound Education Center (TIOBEC) as the President and CEO in 2023. Located on one of the Boston Harbor Islands, TIOBEC’s core mission is to build stronger, more equitable school communities by delivering free experiential learning programs that boost academic success and foster personal growth. TIOBEC is a proud member of the network of 10 Outward Bound schools in the U.S. with a shared mission to change lives through challenge and discovery.

Sylvia holds a Bachelor of Arts in political science from the University of South Carolina and Master of City Planning from the Massachusetts Institute of Technology. She serves as a leader in the following nonprofit/social organizations:   The African American Museum of Philadelphia (Chair, Collections and Exhibits Committee) and Friends of Arch Street Presbyterian Church (Chair).

Sylvia is married to Theos Dickson McKinney, III, an attorney with Constellation. They have a son, Aubrey Hill McKinney II. The family resides in the Seaport area of downtown Boston.

June 2023