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Stephen Caudill has a diverse range of work experience. Stephen is currently serving as a Co-Founder of Origami, a position they started in February 2022. Prior to this, they were a Founder of Stealth, where they played a role in starting Origami. At Reify Health, they worked as a Staff Engineer from August to December 2021. Stephen also worked at Guaranteed Rate as a Software Engineering Manager from November 2020 to August 2021, overseeing multiple teams and contributing to team growth. Stephen was the Co-Founder and Chief Technical Officer at Suiteness from May 2015 to November 2020, leading the development of systems for hotel bookings. As the Team Lead at Outpace Systems, Inc. from September 2014 to April 2015, Stephen spearheaded a major data transformation system rewrite. Stephen also served as a Principal Engineer at Hashrocket Inc from November 2008 to August 2014. Earlier in their career, Stephen founded JamLab, LLC, an online music collaboration platform, and worked as a Lead System Engineer at maccontrol. Stephen started their career as a Team Lead at homes.com.

Stephen Caudill's education history includes attending Y Combinator in 2016. Although no degree or field of study is mentioned for this particular program, it suggests that they likely received some form of specialized training or education during that time. Furthermore, in the years 1999 to 2001, Stephen attended Tallahassee Community College, where they obtained an Associate of Science (AS) degree in Internet Services Technology.