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Jackson Jessup started their career as an intern at Jessup Engineering Inc., where they worked with AutoCAD to modify drawings and create sales layouts. Jackson also assembled computers for the engineering and office staff. Jackson then interned at Spire Integrated Systems, Inc., where they assembled and installed devices into automation server cabinets and established networks for automation systems.

In 2014, Jackson became a Research Assistant at the University of Michigan, where they developed a collaboration client tool for Windows Phone. Jackson then joined Tivvi, Inc. as an iOS Developer, creating app components and collaborating with a design team to develop an appealing UI.

Following that, they worked at jacapps as an iOS Developer, updating apps to support the latest iOS and developing custom apps for clients. Jackson also built a web form for clients to request changes to their apps.

Jackson later joined Google as a Senior Software Engineer, where they worked until 2021. Finally, in 2021, they became the Director of Product Engineering at Switchboard.

Jackson Jessup attended the University of Michigan from 2010 to 2014, earning a Bachelor of Science in Computer Science.