Rachel Skiffer Named New Head of School

Rachel Skiffer will become the next Head of School, starting in the 2022-2023 school year, the School confirmed.

Skiffer’s appointment ends a yearlong search after current Head of School Crystal Land announced her intention to retire in June of 2022. The School — alongside consultants Educational Directions — considered more than 600 candidates for the position, before the Board of Trustees unanimously selected Skiffer.

“[Skiffer] had 100% connection with all of the constituencies she interacted with during her visit on campus,” said Vangeria Harvey, a Board member and co-leader of the Search Committee. “It was important to hear people talk about their belief that they could follow her and that she would honor our community.”

Skiffer, a San Francisco native, is currently the Head of School at Khan Lab School in Palo Alto, Calif. She has held this position since 2018. 

Initially a lawyer, Skiffer earned a J.D. from Harvard Law School and served as Coordinating Editor of the Harvard Law Review. She worked for consultants McKinsey & Company before joining commercial real estate firms in Chicago and San Francisco.

Skiffer notably served as the Dean of Policy and Strategic Planning at Phillips Academy in Andover, MA and the Director of Admissions and Financial Aid at San Francisco University High School. This experience made her an attractive candidate for the Board of Trustees.

“She has independent school experience, both personally and professionally. And that means she knows our culture,” Harvey said. “She knows the marvelous opportunities that allow students to excel not only in the classroom, but in the community.”

The Board of Trustees hopes that Skiffer, who will become the 12th Head in School history, will help the School wrestle with essential questions about its identity, its future, and its place in Oakland.

“I don’t think she will come in saying that she has all the answers to those questions,” Harvey said. “I think what she’s going to say is that, ‘I want to collaborate with you. I want to hear you. I want lead us in that direction.’”

Skiffer imagines the same role for herself.

“I will be joining at a critical time in the school’s history and am honored to have the opportunity to lead Head-Royce through the next evolution,” she wrote in a letter to the School community.