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Weston Trott has a diverse work experience in various industries. Weston started their career at Elections Ontario in 2003 as an Automation Coordinator, where they updated the permanent electors list using software applications. Weston then worked at the City of Toronto, Elections Division, as a Clerk/Technician, where they led continuous voting and conducted logistics and automation testing. In 2004, they worked as a Financial Analyst at the Bank of Montreal.

In 2005, Trott joined Elections Ontario again, this time as a Lead/Supervisor, responsible for call center analysis, system development, and training coordination. Weston then joined Swift Trade as a Proprietary Trader in 2006 and moved to Desjardins in 2007 to set up and execute profitable trading strategies on the London Stock Exchange trading division.

Trott worked as a Business Consultant at Meltwater Group in 2008, where they launched the Meltwater Montreal office and managed sales targets. Weston then worked as a Proprietary Equities Trader at WTS, where they designed and executed profitable trading strategies.

In 2010, Trott joined CN as a Rail Traffic Controller, managing emergency situations, ensuring safety, and maintaining records. Weston later joined Metrolinx in 2012, where they have held various roles including Rail Operations Controller, Manager at the GO Transit Control Centre, Manager at the GO Transit Control Centre (A), Manager of Network Operations Control, Senior Manager of Rail Traffic Control, Director of Network Operations Control, Director of GO Expansion Operations and Rail Traffic Control, and currently serves as the Vice President of OnCorr Operations.

Throughout their career, Trott has demonstrated their expertise in operations management, emergency management, communication, and trading strategies.

Weston Trott attended St. Francis Xavier University from 2001 to 2005. Afterward, they pursued a Bachelor's degree at Athabasca University.