Diana joined the CAPRI team full time in 2018. She was a member of the Taking Responsibility project, the precursor to CAPRI.

She was a lecturer in the Department of Government, UWI, Mona for over a decade, during which time her academic research was focused on Caribbean and small state foreign policy and international political economy. From academia she transitioned to writing, and she wrote a business biography, Mayer Matalon: Business, Politics, and the Jewish-Jamaican Elite (Hamilton Press, 2019).
With a B.A. in English from the University of Virginia, and an M.Sc. in International Relations from the University of the West Indies in Trinidad and Tobago, Diana went on to complete a M.A. and Ph.D. from the Johns Hopkins University School of Advanced International Studies in International Relations and International Economics.

Her present roles outside of CAPRI include advisor to the Minister of Health and Wellness, chairman of the Bellevue Hospital board, member of the Adoption Board, member of the Campion College School Board, and secretary of the St. Thomas Aquinas Parish Advisory Council.

She is also working on a second narrative non-fiction book,  a political history and true crime book that tells the story of how Spanish Town came to be the murder capital of Jamaica.