KCP Principal Jessica Cunningham Wins Milken Educator Award and $25,000


On October 8th, KIPP DC College Preparatory principal Jessica Cunningham received the surprise of a lifetime when she was honored with the prestigious Milken Educator Award. Established in 1987 as an initiative of the Milken Family Foundation, the Milken Educator Awards program rewards and inspires excellence in the world of education by honoring top educators around the country with $25,000 unrestricted awards. You can watch Jessica’s reaction to the surprise announcement here!

Jessica Cunningham joined the KIPP DC Team & Family in 2003, as a sixth grade teacher at KIPP DC KEY Academy. After displaying excellence in the classroom, she was selected for the KIPP Foundation’s Fisher Fellowship and founded KIPP DC’s third middle school, KIPP DC WILL Academy, in the summer of 2006. She spent four years growing WILL Academy into the high-performing middle school it is today before becoming a Chief Academic Officer (CAO) at KIPP DC. As a CAO, she was able to work with principals across our network, as well as the KIPP Through College team, to continue to raise the bar for student success. She could have stayed very comfortably in this role, but instead answered the call to lead our high school in 2012.

Under Jessica’s leadership, KIPP DC College Preparatory has become the highest performing, open-enrollment high school in the District of Columbia. 100% of her seniors are accepted to college each year and they have earned over $8 million in college scholarships. Her graduates include four POSSE scholars, three Stephen Joel Trachtenberg Scholars, one Gates Millennium Scholar, and numerous other full scholarship recipients.

Jessica is relentlessly focused on ensuring that her students are ready to succeed not only in college, but also in competitive careers and as engaged members of their communities. She does not accept anything less than excellence, and she continues to raise the bar each year to ensure that her students can compete with the best and brightest across the country. As she explains, “a high school diploma from KIPP DC should mean something. It should signify a high level of skill mastery, content mastery, and maturity.”

There is no doubt that Jessica has had a tremendous impact on our network. As Susan Schaeffler explains, “to put it in sports terms, Jessica Cunningham is our franchise quarterback or our closer. She not only leads and prepares our high school students for college, but she also inspires our entire KIPP DC region to care more and do more because of her excellence. She knows that our students’ futures depend on what we do today and she is in it for the kids, with the kids year after year.”

We could not be more excited for Jessica to win this prestigious award! Kudos to an amazing member of our Team and Family!

Posted on October 8, 2015 in Awards & Recognition