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Jackson Crain has a diverse work experience history starting from 2019. Jackson began their career as an Intake Specialist at UnitedHealth Group, where they were responsible for ensuring the accuracy and completeness of incoming claims documents before forwarding them to the relevant teams. In 2020, they worked as a Supplemental Health Intern at the same company. In 2021, Jackson joined UnitedHealth Group's Best Practice Unit as part of their role. Moving forward to 2022, they worked at PC Construction Company as a Field Engineer, where they handled RFIs, updated drawings, coordinated with subcontractors for submittals, and performed daily log work and safety inspections. Currently, in 2023, Jackson is employed as a Project Engineer at Landry/French Construction Company.

Jackson Crain attended the University of Maine from 2019 to 2023, where they earned a Bachelor's of Science degree in Construction Engineering Technologies.