Winsome began her career with the prestigious accounting firm Giant PricewaterhouseCoopers (PwC) in Kingston, Jamaica. She subsequently spent approximately 10 years managing the accounting & finance functions for several small and medium sized companies in Kingston, Jamaica and South Florida area. She also spent approximately 3 years as a Sarbanes Oxley Consultant for several large publicly traded companies located in South Florida including AutoNation and Levitt Corporation. Winsome graduated from the University of Technology, Jamaica with a high honors diploma in Business Administration, majoring in accounting. She is a Certified Public Accountant licensed in the states of Florida and California.