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Simon Gerstler has a long and varied work experience. Simon began their career in 1995 as a Trainee Accountant at Price Waterhouse Coopers. Simon then moved to London Pearl Company in 1996, where they were a Sales Manager. In 1998, they became a Sales Manager at Tom James of London. In 2000, they joined TotallyLegal.com (acquired by Reach plc) as a VP Sales, and in 2013 they took the same role at Graduway. In 2020, they became Co-Ceo at Pipe Global, VP Sales at Woo.io and Lumina Spark & Sales coach at Lumina Learning.

Simon Gerstler attended Haberdashers' Aske's School, Elstree from 1983 to 1990. Simon then earned a BSc Econ Hons 2.1 from The London School of Economics and Political Science (LSE) in 1995. In 2020, they obtained certifications as a Lumina Sales coach and a Lumina Spark coach from Lumina Learning.