Winston has been a member of Bethel Baptist Church since 2007. He is an economist who has developed a professional career in the financial sector, holding a wide range of managerial assignments. Those assignments included credit and portfolio management, customer relationship management, marketing, human resources management, sales, and business development. He holds a Master of Science (MSc) in Economics and a Bachelor of Science (BSc) in Economics and Statistics (Hons) from the University of the West Indies, Mona.