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Dylan Bosak has a diverse range of work experience, starting in 2010 as a General Contractor at Bosak Construction. From 2015 to 2015, they worked as an Assistant Surveyor at Maidment Land Surveys Ltd. Dylan then transitioned to the City of Lethbridge in 2017, where they served as a GIS Data Clerk until 2018. Following that, they joined Sandul's R&R Ltd. as a Rental Property Manager from 2016 to 2018. Most recently, since 2018, Dylan has been working at Matrix Solutions Inc. as a GIS Analyst and Team Coordinator.

Dylan Bosak completed a Diploma in Geomatics Engineering Technology from the Southern Alberta Institute of Technology (SAIT) from 2014 to 2016. After that, they pursued a Bachelor of Science degree in Geography - GIS at The University of Lethbridge from 2016 to 2018.