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Jake Workman has a solid work history, starting their career as a Software Engineer Intern at Fastek International Ltd. from September 2011 to April 2013. Jake then joined Collective Data as an Application Developer, later transitioning to Solutions Engineer and eventually becoming a Senior Solutions Engineer. Jake worked at Collective Data from May 2013 to April 2017. Jake then moved on to UnityPoint Health as a Principal Solutions Engineer from April 2017 to September 2019. Jake then joined ReCharge Payments, initially working as a Manager, Solutions Engineering from September 2019 to March 2021, and later as a Director, Solutions Engineering from March 2021 to August 2022. Presently, Jake is the Head of Engineering at Chek, starting in August 2022.

Jake Workman attended Coe College from 2009 to 2013, where they earned a Bachelor of Arts (BA) degree in Computer Science.