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Dejan Trajanoski has a diverse work experience spanning several industries. Dejan started their career in 2000 as a bartender at Caffe Cinema and later worked as a sales specialist at H&M in 2007. From 2008 to 2012, they served as a manager at Caffe ADMIRAL. In 2005, Dejan worked as an inspector at the Macedonia Ministry of agriculture, forestry, and water economy. From 2009 to 2015, they worked as a sales agent at ONE - Telecommunications Services SC Skopje. In 2015, they became an agricultural inspector at the Agricultural Inspectorate, where they worked until 2018. Dejan then joined Slice in 2018 and held various roles including account manager, restaurant support representative, and team lead of the restaurant support department. Dejan left Slice in 2023 and briefly worked as an operations assistant at the Fridenson Group. Dejan then joined BAZAN Group Oil Refineries Ltd as a technical support associate before returning to Slice as a partner success manager for major accounts in June 2023.

Dejan Trajanoski attended the Faculty of Agriculture Skopje from 2001 to 2005, where they earned a VII degree in Agricultural Mechanics and Equipment/Machine Technology.