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Winston Wright has worked in a variety of positions since 2005. Winston began their career as a Project Engineer at Proyectos de Automatización Industrial S.A. (PRAI), where they designed and developed automation projects. In 2007, they joined Enel as an Automation Engineer, where they managed the Project EGP-GMS for Latin America. Winston also worked as a Business Developer and Business Developer Jr. at Enel, where they were responsible for handing over a 50MW project and compiling and generating documentation for Internal and Governmental approval of a 50MW Hydroelectric Project in Costa Rica. From 2010 to 2015, Winston Wright acted as a co-owner and investor in the family business Ciros Bar Restaurante, developing their in-house ERP-like software and adapting the family business to become a small enterprise. Winston then worked as CTO at Moodbox Media in 2015. In 2018, Winston Wright worked as a Tech Lead for Software Freelancing. In 2019, they took on the role of DevOps Engineer at Advision Development. Currently, Winston Wright is a Cloud Service Delivery Development Lead and Cloud Engineer at Escala 24x7 Inc.

Winston Wright obtained a Licenciatura in Industrial Maintenance Engineering from Tecnológico de Costa Rica between 2001 and 2006. In February 2021, they earned an AWS Certified Solutions Architect – Associate certification from Amazon Web Services (AWS).