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Matthew Gleeson has a diverse work experience spanning various industries and roles. Matthew started their career as a Student Intern at UW Medicine in 2015, where they worked as an office assistant and assisted in organizing workshops for medical staff. In 2016, they co-founded a nonprofit organization called Hatch, focused on community-driven renewal projects. Matthew then worked as a Server and Busser at 8OZ BURGER CO. LIMITED and a Bartender and Server at Kangaroo & Kiwi Pub. In 2017, they served as an Assistant Chef at St. John Catholic School. In 2018, they worked as a Customer Service Coordinator at Accents & Interiors and a Line Cook at King's Hardware. Matthew later joined LIGHTHOUSE UNIFORMS, INC. as a Customer Service Representative and Operations Support. In 2020, they transitioned to Strategy Labs as a Media Buyer and continued in the same role at Sway Creative Labs in 2023.

Matthew Gleeson earned their Bachelor's Degree in Business Administration with a focus on Marketing from Western Washington University, where they attended from 2013 to 2017. Prior to that, they completed their high school education at Bishop Blanchet High School, graduating in 2013. In addition to their academic degrees, Matthew obtained a Ski Instructor certification from the Professional Snowsports Instructors of America - Northwest in February 2013.