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Andrea Oleari's work experience begins in 2002 when they worked as a Principal Application Engineer at Meta System Racing Service. They then went on to work as an Application Engineer at Aprilia Racing S.R.L. from 2003 to 2006. Andrea then joined Ducati Motor Holding as an Application Engineer from 2006 to 2009. In 2009, they moved to MARC VDS Racing Team where they continued to work as an Application Engineer until 2013. Andrea then joined Mahindra Electric Mobility Limited as an Application Engineer from 2013 to 2014. In 2014, they became the Crew Chief at GO FORWARD RACING, INC., a position they held until 2017. In 2015, Andrea joined MV Agusta Motor S.p.A. as a Technical Project Coordinator, a role they held until 2017. Most recently, Andrea worked as a Suspension Engineer at Öhlins Racing AB starting in 2017.

Andrea Oleari completed their education from 1995 to 2000 at the Università degli Studi di Modena e Reggio Emilia, where they obtained a degree in mechanical engineering, known as "Laurea ingegneria meccanica." No information is provided regarding any specific field of study.