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Simon Fletcher has a diverse work experience spanning various roles in the tech industry. In 2008, they worked as a Lead Developer at Youmeo. From 2010 to 2011, they served as a Full Stack Engineer at CV - Christian Vision. In 2013, they joined BakedCode as a Co-Founder and Engineer, where they played a vital role in the development of their project management system, Interstate. BakedCode was later acquired by Stripe in 2013. Also in 2013, Simon worked as a Consultant at Mavenlink. In 2016, they became a Senior Software Engineer at Airbnb, and in 2018, they co-founded Stopwatch, assuming the role of CTO. Currently, they hold the position of Engineering Manager at Twingate, starting in 2022.

Simon Fletcher attended The Whitby High School, where they studied IT, Business, and Economics. After leaving high school, they enrolled at Y Combinator in 2011, although specific details about the degree or field of study are not provided.