Winsome hails from the parish of Manchester where she completed high school before moving on to the Mona campus of the University of the West Indies in 1964. She had become a Christian in 1962 and found opportunity for fellowship, spiritual growth and Christian service in the ministry of the Inter-Schools and Inter-Varsity Christian Fellowship.
Having chosen teaching as a career, Winsome acquired a Diploma in Education at UWI and then taught at Wolmer’s Boys School in Kingston. In 1973 she studied for an Advanced Certificate in Education at the University of Bristol in England and returned to Jamaica as a lecturer at the Mico Teachers’ College in Kingston.
The call to full time Christian ministry was received in 1974 while attending the Lausanne Congress on World Evangelization in Switzerland, and was answered in 1976, when she was sent from Deeper Life Ministries in Kingston to serve in the ministry of Teamwork Associates in Montego Bay.
Alongside administration and education, Winsome continued academic work and earned a Masters in Christian School Administration from the Oral Roberts University in the USA in 1994 and a PhD from the University of Birmingham in England in 1998.
Winsome is currently the Executive Chairman of Teamwork Associates and has resumed direct involvement in the education and training offered by Teamwork School through the Career Online High School Programme in partnership with Smart Horizons Career Online Education and Education to Go of the USA.
Winsome and Menzie were married in 1978 and have two adult children. Sarah works for the government of Jamaica and Paul serves the ministry of Teamwork Associates in various capacities.