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Deep Tailor has worked in a number of roles since 2012. From 2012 to 2015, they worked as a Wealth Management Advisor at Northwestern Mutual. In 2015, they became a Systems Administrator at Oakton Community College. In 2016, they became a Full Stack Developer while self-employed. From 2017 to 2021, they worked at NASA Ames Research Center as a Principal Software Engineer, Technical Lead, Senior Software Engineer, and Software Engineer. In 2021, they began working as a Principal Software Engineer at Epsilon3.

Deep Tailor has a Bachelor of Science (B.Sc.) in Finance from Purdue University, which they obtained in 2013. In 2016, they attended App Academy and earned a Software Developer certification in Computer Science. In 2020, they obtained a Triplebyte Certified Front End Engineer certification from Triplebyte. In 2013, they also obtained Series 63 and Series 6 certifications from the Financial Industry Regulatory Authority (FINRA).