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Jessica Fairley has worked at three different companies in their career. Jessica started off at GEICO in 2004 as a Senior Instructional Designer and remained in that role until 2016. Jessica then joined the University of Maryland University College as an Instructional Designer from August 2016 to February 2018, and later became a Change Management Consultant in the same institution from February 2018 to June 2019. Jessica's most recent role is at AccelerEd, where they started as a Change Management Consultant from June 2019 to April 2022. Jessica then became a Program Manager from April 2022 to April 2023, and is currently the Director of Learning and Innovation, starting from March 2023.

Jessica Fairley completed their Master of Science degree in Learning Design and Technology from the University of Maryland Global Campus in 2019. Prior to that, they obtained a Bachelor of Arts degree in English and Human Communication Studies from the State University of New York at Fredonia between 1999 and 2003. In October 2018, they also obtained a certification as a Prosci Certified Change Practitioner from Prosci.