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Alan Caulkins has a diverse work experience spanning over multiple industries. Alan is currently working as a Software Engineer at Commsor since February 2023. Prior to this, Alan worked at Jaxon, Inc. as a Machine Learning Engineer from March 2019 to February 2023. During their time at Jaxon, they were involved in developing an AI platform that trains other AI to understand natural language from raw text. Before Jaxon, Alan was a Principal Computational Engineer at BigR.io from April 2015 to March 2019. At BigR.io, they specialized in Big Data, Machine Learning, and Custom Software strategy, analysis, and implementation. Alan is also the Founder of Green Country Technical Services, a company they started in June 2009 and ran until April 2015. Prior to that, they worked as a Programmer/Analyst at St. John's Health System from April 2006 to April 2012. Alan's early work experience includes being a Student Systems Administrator at Kansas State University in 1999.

Alan Caulkins attended Worcester Polytechnic Institute from 1994 to 1998, where they studied computer science. Alan later pursued a Bachelor of Science degree in computer science from Kansas State University, graduating in 2001.