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Robby Grossman has extensive work experience in the technology industry. Robby joined Digital Sublimity in 2001, where they founded a consulting firm that helped small businesses sell products and services online. Robby continued working in client services through college until 2007. In 2007, they joined SAP Labs as a Software Engineer, focusing on natural language processing software and refactoring legacy products. After two years, they transitioned to oneforty as a Software Engineer, where they were part of a team that built and launched a successful product within six weeks. In 2009, Robby worked for various political campaigns as a Technology Consultant, where they developed software for Google Maps route planning and online contribution tracking. In 2011, they joined Shareaholic, Inc. as a Tech Lead until 2013, when they moved on to become a Founder of PaperPhobic. Robby then joined Wistia in 2013, initially as an Engineer before becoming the Director of Engineering. Currently, Robby holds the position of VP of Engineering at Wistia, where they lead a high-performing team in scaling engineering and utilizing video for businesses.

Robby Grossman pursued their undergraduate studies from 2003 to 2007 at Wheaton College Massachusetts, where they obtained a Bachelor of Arts degree with a major in Computer Science. Following this, they furthered their education at Harvard University from 2008 to 2011, earning a Master of Liberal Arts degree. During their time at Harvard, Robby specialized in the fields of Management, Finance, and Control.