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Jason Benson has a diverse work experience. From 2006 to 2011, they worked as an Antiquarian Horologist (Clock Maker) at Gordon Converse & Co. where they repaired and restored antique clocks. In 2011, they joined Quench USA, Inc. and held various roles. From 2011 to 2012, they worked as a Technical Support for Field Operations, providing technical assistance and resolving inventory and billing issues for field technicians. From 2013 to 2013, they served as a Third Party Service Coordinator, managing service with third-party vendors and ensuring customer requests were met within promised response times. Since 2014, they have been working as a Technical Support and Data Integrity professional, specializing in back-end database support, data integrity for customer accounts and field inventory, and remote desktop support for various operating systems.

Jason Benson attended Western Center For Technical Studies from 1996 to 1997, where they obtained a Certificate of Completion in Commercial and Advertising Art. Following this, they enrolled at The Art Institutes from 1998 to 2000, earning an Associates degree in Computer Animation. Additionally, Jason Benson holds a certification from edX for Excel for Data Analysis and Visualization, but no specific information regarding the month or year of attainment is provided.