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Connor Obrien has a diverse work experience, starting with their role as an Assembly Line Worker at Lavelle Industries, Inc. in 2017. Connor then worked as a Landscaper, where they prepared yards for a wedding by conducting various tasks such as mulching, tree planting, and lawn care. In 2018, they joined Fort Atkinson Parks and Recreation as a Softball/Baseball Umpire, Tball and Coach Pitch Instructor, and later became a Youth Center Supervisor. That same year, they also served as a Varsity Assistant Basketball Coach at Cambridge High School. In 2019, they joined Spacesaver Corporation as a Paint Line Loader before transitioning to the position of Marketing Intern and, eventually, Marketing Specialist. In their marketing roles, they coordinated trade shows, managed digital advertising campaigns, oversaw social media channels, conducted market research, and contributed to product development.

Connor O'Brien attended the University of Wisconsin-La Crosse from 2018 to 2022. Connor studied Business Administration and Management, General during this period, although no specific degree information is available.