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Josh Hollinshead began their work experience as a Webmaster at Quality Crop Link in November 2012 and held this position until October 2014. In November 2013, they joined Alphero as a Developer, where they built functional and award-winning web applications and was responsible for various hosting solutions. Josh worked at Alphero until July 2017. Since July 2017, Josh has been employed at HotDoc, initially as a Software Engineer and later as a Senior Software Engineer.

Josh Hollinshead earned a Bachelor's degree in Computing and Mathematical sciences (First class Honors) from The University of Waikato. Their studies at the university from 2011 to 2014 focused on cyber security, networking, and web application development. In January 2020, they obtained a certification in Strategic Thinking from LinkedIn.