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Jessica O'Leary has a diverse work experience history. Jessica began their career as an Intern at SUNY Fredonia Technology Incubator in August 2017 and worked there until May 2018. In May 2017, they joined DICK'S Sporting Goods as a Cashier and stayed with the company until August 2020. Following that, in December 2019, they joined Columbus McKinnon as an Order Entry professional and worked there until June 2021. Jessica is currently working at Osmose, where they started as a Production Technician in June 2021 and later became a Project Coordinator in May 2022.

Jessica O'Leary received their high school diploma from Williamsville East High School in 2014. Following that, they went on to attend the State University of New York at Fredonia from 2014 to 2018, where they obtained a Bachelor's degree in Business Management.