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Olivia Shirlaw's work experience begins in 2011 as a Front of House employee at The Old Court Hotel. From 2018 to 2018, they worked as a Sports Assistant & Resident Assistant at Christ College Brecon. In 2019, Olivia had multiple roles: a Chalet Manager at Scott Dunn from March to May, a Graduate Role in Residential Management at Canary Wharf Group plc from September to November, and a Residential Graduate and Operations & Administration Coordinator at Vertus from September 2019 to November 2021. Their most recent position is a Client Success Associate at WiredScore, which they started in January 2022.

Olivia Shirlaw completed their Master of Arts (MA Hons) degree in Geography from The University of Edinburgh from 2014 to 2018. Prior to that, they attended Hereford Sixth Form College from 2012 to 2014, where their degree and field of study are unknown. From 2010 to 2012, Olivia attended Hereford Cathedral School, and in 2009 to 2010, they were a student at Haberdashers' Monmouth Schools, with no specified degree or field of study. Olivia also attended Abberley Hall at some point, though the start and end year are unknown. Currently, they are pursuing the Level 2 Foundation Build to Rent Exam at IRPM, which is expected to be completed in 2021.