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Winston Blackwood has extensive work experience in the field of project management and engineering. Winston started their career in 2013 as a Systems Engineer at Facilities Management Systems Limited. From 2014 to 2015, they also served as the Managing Director at Avid Pupil. In 2015, they joined Jamaica Public Service Company Limited as a Project Manager and later transitioned to the role of Manager for Smart Grid Projects and Services in 2017. Currently, they hold the position of Head of Department for Digital Transformation and Business Effectiveness at Jamaica Public Service Company Limited.

Winston Blackwood, PMP, MSc, pursued a Master of Science in Engineer Management from Florida International University from 2018 to 2019. Prior to that, they completed a degree in Electrical and Computer Engineering, with a specialization in Power and Control Systems, from the University of the West Indies, St. Augustine Campus from 2010 to 2013. Winston also holds additional certifications in Professional Scrum Master I (PSM I) from Scrum.org and Project Management Professional (PMP) from the Project Management Institute, obtained in 2021 and 2018 respectively.