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Jason (Jross) Ross began their work experience in 2011 at Apple, where they served as an Expert from April 2011 to February 2014, and as a Business Specialist from February 2014 to August 2014. In 2014, they joined Jobber as an Account Manager and worked in that role until September 2017. Jason (Jross) then transitioned to the position of Sales Manager at Jobber from October 2017 to June 2018. Jason progressed within the company and became a Director of Sales from July 2018 to July 2021. Currently, they hold the position of VP, Sales at Jobber starting from July 2021. In addition, they briefly spent time as a Member at Revenue Collective from April 2021 to July 2021.

Jason Ross attended ESSMY from 2005 to 2008, where they earned a High School Diploma in the field of study of High School.