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Jessie Benson has a diverse work experience in various design and managerial roles. Most recently, they worked at MillerKnoll as a Design Technology Enablement. Prior to that, they founded and worked as a Designer at SWEPT Design LLC, where they utilized design technology for furniture solutions. They also have experience as a Design Manager, Design Lead, and Healthcare Designer at Intereum, where they were responsible for managing the design department and training the team. Jessie Benson started their career as a Design Intern at BDH&Young and later worked as an Administrative Assistant at the College of Design, University of Minnesota. Additionally, they have prior experience as a Retail Manager at Everyday People, where they managed a team and handled purchasing and buying lessons.

Jessie Benson pursued their education from 2006 to 2010 at the University of Minnesota. During this time, they successfully earned a Bachelor of Science degree in Interior Design.