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Stephen Olsen began their work experience in 2010 as a Software Developer at Quad/Graphics. From 2012 to 2014, they worked as a Software Developer at Arc90, where they primarily collaborated with an insurance company to build internal tools for their business. In 2014, they joined The Groundwork as a Senior Software Engineer and stayed until 2017. At The Groundwork, they contributed as a Senior Software Engineer. Following this, they worked as a Senior Software Engineer at Artsy from 2017 to 2019, focusing on building tools and infrastructure for other teams. From 2019 to 2023, Stephen served as a Software Engineer at Oso, where they played an integral role in the business, overseeing various projects and specializing in a custom programming language and libraries for popular programming languages. Currently, Stephen is a Senior Software Engineer (Backend) at Close, commencing in 2023.

Stephen Olsen attended the University of Wisconsin-Milwaukee from 2008 to 2012, where they earned a Bachelor of Science (B.S.) degree in Applied Mathematics and Computer Science.