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Josh Gilson has a diverse work experience. Josh started their career as a Private Tutor at Tutors for Africa from an unknown start date to 2016. Then, in 2018, they worked as an Evidence-based Management Marking Assistant at the University of Cape Town. In 2019, they joined KPMG South Africa as an Audit Trainee until February 2022. Later in 2022, they worked as a Strategic Analyst at Zee - Importer of Record for two months. Currently, they are a Revenue Operations Manager at Playroll, starting in November 2022. Josh also had a previous role at Playroll as a Business Analyst from May 2022 to November 2022.

Josh Gilson attended the University of Cape Town from 2014 to 2017, where they earned a Bachelor of Business Science degree in Finance with Accounting. In 2018, they continued their education at the same university and obtained a Postgraduate Diploma in Accounting. In November 2018, Josh Gilson also completed a certification course called "Financial Regulation in Emerging Markets and the Rise of Fintech Companies" through Coursera.