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Jonathan Riley has a diverse work experience spanning various industries. Jonathan began their career in 2012 as a Cost Accountant at PJ Dick - Trumbull - Lindy Paving, where they worked until 2016. During their time there, they also worked as a Project Engineer. In 2017, they joined Penske Truck Leasing as a Sales and Operations Trainee and later moved up to become an Assistant Rental Manager and then a Branch Rental Manager. In 2022, they joined New York Life Insurance Company as a Financial Services Professional and worked there until 2023. Currently, they are working as an Account Executive at PLS Logistics Services.

Jonathan Riley attended Florida Southern College from 2012 to 2016, where they obtained a Bachelor's degree in Business, Management, Marketing, and Related Support Services.