Previously, she taught English Language Arts for 11 years at Oak Park River and Forest High School (OPRFHS) in Oak Park, Illinois, where she worked to interrupt systemic racial achievement disparities. Her work at OPRFHS is featured in Steve James’ 2018 documentary series, America to Me.

In 2014, Jessica received a Fulbright Distinguished Award in Teaching, and spent a semester in Wellington, New Zealand, studying educational debts between white and indigenous Māori students.