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Maddi Olsen-Weston has a diverse work experience spanning different industries and positions. In 2012, they began their career as a Media Advisor at JB Hi-Fi. Maddi then joined Vodafone in 2015 and worked as a Retail Sales Assistant before being promoted to Assistant Store Manager. In 2018, Maddi joined the Overland Footwear Group and served as a Retail Sales Assistant and later as an Assistant Store Manager. Maddi then worked at Channel 1 Creative Media as a Production and Graphic Design Assistant from 2020 to 2021. In 2021, Maddi joined the City of Boroondara as a Placement Student, where they planned, developed marketing for, and co-facilitated a youth LGBTQIA+ group called "Skittles" and co-facilitated school holiday programs. Currently, Maddi works at MacKillop Family Services as a Youth Residential Care Worker and has also held positions as an Assistant Residential Care House Supervisor and Targeted Care Packages Case Manager since June 2022. Overall, Maddi has gained skills in customer service, retail management, graphic design, and youth support throughout their work experience.

Maddi Olsen-Weston pursued their education from 2019 to 2021 at Swinburne University of Technology, where they obtained a Certificate IV in Youth Work. Their field of study was focused on Youth Work.