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Kevin Leary has worked for two companies, Open Security, Inc. and Quirk Chevrolet - Portland. Kevin began working for Open Security, Inc. in 2022 as a Business Development Representative. In 2021, they began working for Quirk Chevrolet - Portland as a Finance Manager. Kevin currently holds this role.

Kevin Leary attended the University of Maine from 2011 to present and earned a Bachelor of Business Administration - BBA in Business, Management, Marketing, and Related Support Services.