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Jessica Cunningham DC 15 Milken Educator Award bio

Jessica Cunningham (DC '15)

Executive Director

KIPP Schools
Philadelphia, PA

At the time of the Award, Jessica Cunningham was:

KIPP DC College Preparatory PCS
Washington, DC

Biographical Information

Success in the classroom and natural leadership ability led Jessica Cunningham from teaching to becoming the principal in 2012 of KIPP D.C. College Preparatory, which has undergone an extensive renovation. KIPP Prep is the highest performing open enrollment high school in Washington, D.C. Cunningham’s impact is felt not only in her school, but throughout the nation.

In the KIPP national network of free, open-enrollment, college-preparatory public schools located in underserved communities, Cunningham is considered “a franchise quarterback.” The schools incorporate a longer day and a commitment to motivating students to attend college.

The school boasts D.C. CAS (Comprehensive Assessment System) proficiency rates that increased by 19 points in math and reading during her tenure, with 20% of students enrolled in the special education program. In 2014, the school posted a math proficiency rate of 95% and a reading proficiency rate of 71%. The graduation rate is 99% and the college matriculation rate is 89% for 2013 and 2014.

Cunningham, whose mother was a teacher, is respected by students for telling them the truth, holding them accountable and suggesting great practices to correct their mistakes. She identifies with them and likes to provide opportunities for the students, many from challenging backgrounds, to make a fresh start. They see her as someone they aspire to be.

College readiness is a priority for Cunningham, who invites guest speakers in to inspire career goals. When the high school opened, the average ACT score was 16.9. It is now 18.9. She gets parents and other family members involved.  When students are not performing up to expectations, she is quick to call their parents. Cunningham also works closely with the college counseling team to ensure students partake of scholarship opportunities.

Cunningham has been part of the KIPP system for 11 years. She started out as a teacher and then became the founding principal of KIPP D.C. Will Academy, the third KIPP middle school to be established in the District. Will Academy had the highest overall growth of all D.C. charter schools in 2009-2010. All eighth grade students attended a top choice high school.

An Aspen Scholar, Cunningham is a role model to fellow educators. She develops curriculum and delivers professional development as part of the KIPP Foundation’s School Leadership Program. She informally mentors several school leaders around the country and she coaches KIPP national administrators.

Cunningham graduated with a bachelor of science degree in African-American history from Florida A&M University in 2000 and a master’s in education from American University in 2003. 

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Jessica Cunningham Newsletters

New Beginnings
Oct 09, 2015

Jessica Cunningham In The News

D.C. Principal Tagged as an Outstanding Educator
Afro-American Newspapers  |  Oct 14, 2015  |  Washington, DC

Q&A: DC Principal Jessica Cunningham, Winner of the ‘Oscar of Teaching,’ Talks Educational Excellence
The Seventy Four  |  Oct 12, 2015  |  New York, NY

D.C. Principal Receives Milken Educator Award
WJLA-TV  |  ABC  |  Oct 08, 2015  |  Arlington, VA

D.C. Principal Receives $25,000 Award
The Washington Post  |  Oct 08, 2015  |  Washington, DC