In the coming weeks, the board of Portland Public Schools will vote on Superintendent Guadalupe Guerrero’s proposed $823 million budget and review long-awaited recommendations on school safety initiatives while district leaders continue contentious negotiations with a restive teachers union.
All of that will likely happen without key members of the district’s administrative team, including the deputy superintendents overseeing both instruction and finances, as illness and vacancies have depleted top ranks.
Deputy Superintendent of Instruction and School Communities Cheryl Proctor has been on medical leave for several weeks, she and other district leaders said. Proctor told The Oregonian/OregonLive that she is “on a protected approved medical leave and will not comment on the conditions of my leave.”
The deputy superintendent of business and operations position has been vacant for more than nine months, since Claire Hertz retired in June 2022 after four years in the role.
Proctor, the district’s former chief academic officer, was promoted to her current role in January 2022. She oversees all teaching and learning, including all principals, curriculum, instruction, special education and testing, and was a key architect of the proposed budget for the coming school year, which is the first to fully confront the dual challenges of the district’s plunging enrollment and the looming end of generous federal pandemic aid.
Proctor’s leave comes as Chief Financial Officer Nolberto Delgadillo is also on medical leave. He is scheduled to return to his post on limited hours within the next week or two, said Jonathan Garcia, chief of staff to Guerreo.
Chief of Schools Jon Franco, who reports to Proctor, recently interviewed for another job even though he has been in Portland less than a year. He remains with Portland Public Schools after being named a finalist, but not the ultimate choice, for the superintendent’s job at the Hillsboro school district.
Turnover has been a consistent issue for the district’s upper management team under Guerrero, who has been at the district’s helm for six years, a relatively long tenure for the superintendent of a large urban district. But Proctor is the third person in her role during that same time frame, after the departures of Yvonne Curtis in 2019 and Kregg Cuellar in 2021.
Proctor was a key player behind the district’s plan to balance its budget for 2023-24 in part by trimming the jobs of 50 teachers on special assignment. They coach teachers on curriculum adoption and rollout.
At a school board meeting Tuesday, Chief Academic Officer Kimberlee Armstrong, who was named to that role in July 2022, stood in for Proctor to outline learning initiatives in the proposed general fund budget, which includes money for day-to-day operations and grant programs, like those that target vocational education and student mental health. Armstrong highlighted new initiatives including the planned Center for Black Student Excellence and hiring of a districtwide civil rights coordinator.
That budget plan represents a relatively tiny $19 million, or 2.4%, increase from the current budget, reflecting the enrollment declines and lessening of federal pandemic aid.
The district has also relied on Proctor on occasion to be one of its contract negotiators with the Portland Association of Teachers. Negotiations began in October and the two sides remain far apart on key points, including mandated class size caps and salary increases. The current contract expires in June.
Meanwhile, recommendations for how to improve student safety and security on campus — an issue that picked up new urgency this year after a series of gun-related incidents just outside of several of the district’s high schools — are due to be presented to the school board May 9.
— Julia Silverman, @jrlsilverman, jsilverman@oregonian.com
