[2] Jackson's education career began as a social studies teacher at South Shore Community Academy High School.

[2] While working as a teacher at South Shore Community High School, Jackson continued to study at Chicago State University, getting a master's degree in history.

[2] The school, located in a previously closed Chicago Public School building located near the Garfield Park Conservatory in the East Garfield Park neighborhood, was centered on providing intensive support for a small student body of under 400, emphasizing the study of technology, science, and the environment.

[2] While Al Raby High School's principal, Jackson began attending University of Illinois at Chicago to earn a second master's degree in education, this time in leadership and administration.

[3][2] She continued University of Illinois at Chicago, studying in its Urban Education Leadership doctorate program.

[3][2] On December 8, 2017, Jackson took office as the interim CEO of Chicago Public Schools, after Forest Claypool resigned.

[3] Jackson established the Great Expectations mentoring program, which seeks to encourage black and hispanic men to pursue careers in leadership at Chicago Public Schools, where they are underrepresented in administrative positions.

[3] In reaction to these revelations, Jackson published a four-page action plan that was distributed to Chicago Public School employees and earmarked $500,000 for a comprehensive review to be headed by Maggie Hickey (a former United States attorney and former Illinois executive inspector general) and the law firm Schiff Hardin.

[3] She changed policy, moving to forbid employees from accessing school buildings when an accusation made by a student against them is still being investigated.

[3] She was also criticized for failing to attend meetings of the Illinois State Board of Education and the Chicago City Council on the matter, to which she had been invited.

However, Lightfoot did not commit to firing Jackson if elected, and conceded, "I'm willing to hear her out, but she is going to have to demonstrate to me that she understands she made a mistake and rectify that with the parents and the teachers and the kids".

[12] After announcing her planned departure, Jackson's leadership in the role of CEO was praised by Mayor Lightfoot and president of the Chicago Board of Education Miguel del Valle.

[14] Jackson declined to run 2023 Chicago mayoral election, claiming to have no interest in seeking the office.