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Ryan Benson has extensive work experience in the technology field. Ryan is currently working at Liberty Mutual Canada as the Vice President Head of Technology since April 2023. Prior to this, they held the role of Vice President Technology at the same company from April 2021 to April 2023. Before joining Liberty Mutual Canada, Ryan worked at Liberty Mutual Insurance as the Assistant Vice President of Technology from August 2019 to April 2021. Ryan also has a significant tenure at BGRS, where they held various roles including Director of Information Technology Operations from September 2016 to July 2019, Senior Manager of Global Information Support Services from November 2014 to September 2016, Manager of Quality Assurance from December 2009 to November 2014, Team Lead of Quality Assurance from November 2008 to December 2009, and Quality Assurance Analyst from December 2007 to November 2008. Earlier in their career, Ryan worked as a Systems Analyst at MCAP from March 2007 to December 2007 and as a Senior Client Support Specialist at M.R.S. Company Ltd. from January 2005 to March 2007.

Ryan Benson attended Seneca Polytechnic from 2000 to 2003, where they obtained a CTY degree in Computer Science. In addition to their formal education, they also have several certifications. Ryan obtained the "Learning from Failure" certification from LinkedIn in March 2021, the "Cultivating a Growth Mindset" certification from LinkedIn in June 2020, the "General Insurance Essentials" certification from the Insurance Institute of Canada in December 2019, and the "ITIL Foundation Level" certification from AXELOS Global Best Practice in April 2019.