Winstead is an attorney with Ballard Spahr LLP in Washington, DC. A former Maryland Secretary of Transportation, Winstead's career combines broad private and public sector experience. He previously served as Commissioner of Public Buildings at the U.S. General Services Administration, the Executive Director of the Washington/Baltimore Regional Association, and President of the American Association of State Highway and Transportation Officials. Winstead chaired the National Commission to Ensure Consumer Information in the Airline Industry.