KIPP DC College Preparatory Principal Jessica Cunningham talks with reporters after the announcement of her $25,000 Milken Educator Award. (Milken Family Foundation)

Jessica Cunningham, principal of KIPP DC College Preparatory, became the first educator this year to win the Milken Educator Award, which comes with a $25,000 cash prize.

The surprise announcement was made during an assembly at the high school on Thursday.

“Jessica has been identified as one of KIPP’s top educators,” said Lowell Milken, chairman and co-founder of the Milken Family Foundation, who announced the award. “She is a teacher leader who takes very seriously her mission to ensure her students are prepared to compete in high school, college and, ultimately, the workplace.”

The surprise visit kicked off the award season for the 2015-2016 school year. The foundation will give out cash awards to educators in up to 40 schools nationwide during the next six months.

Launched in 1987, the awards go to mid-career educators who have an outstanding record of achievement. They are selected with the help of state education agencies.

Cunningham has worked for KIPP for 11 years, starting as a teacher before becoming the founding principal of KIPP DC WILL Academy, a middle school. In 2012, she became principal of KIPP DC College Preparatory, which moved into a new campus this fall. Her colleagues credit her with attaining strong results for students.

“To put it in sports terms, Jessica Cunningham is our franchise quarterback or our closer,” said KIPP founder and chief executive Susan Schaeffler. “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.”