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Ana Chukalevska has 18 years of work experience in various roles. Ana is currently working as a Customer Service Specialist at heloo since March 2022. Prior to this, they worked at KAMFUD dooel as an Assistant Manager from September 2013 to October 2017. Before that, they were a Class teacher in Dutch language at Private School Abacus in Ohrid from October 2012 to January 2013. Ana also served as the General Manager at generalturist ohrid from June 2011 to April 2012. Additionally, they worked as the Manager for ECTS & Student Affairs at University St. Paul the Apostle University for Information Science and Technology from July 2009 to August 2010. Ana started their career at EWI Institute where they worked on a project related to Balkan cross-border cooperation from December 2004 to March 2006.

Ana Chukalevska's education history includes attending the University St.Kliment Ohridski- Bitola from 2001 to 2005. Ana obtained a degree in Public Administration, specializing as a Manager for public administration. Additionally, they attended Volks University in Haarlem, The Netherlands, from 2009 to 2010. However, no specific degree or field of study was mentioned during their time at Volks University.