Portland School Board Will Weigh Contract Extension for Its Superintendent That Includes a Raise

The Portland School Board on Tuesday night will consider a contract extension with its superintendent. If approved, Dr. Kimberlee Armstrong’s compensation package will increase.

The pay increase, which largely comes in the form of a retention incentive that starts in June 2028, comes as Armstrong is under intense scrutiny as she navigates school closures and teacher layoffs. The district has faced years of budget shortfalls, and made more than $50 million in cuts this spring.

Armstrong, who joined the district in the 2024–25 academic year, has begun her third year as superintendent in Oregon’s largest school district. If approved, Resolution 7371 will extend her contract through June 30, 2029, on terms “set forth in the amended employee agreement.”

The proposed contract, a copy of which was shared with WW, sets Armstrong’s base pay at $344,792 a year. That base pay salary will be increased by 3% each year, or equivalent to the cost-of-living adjustment provided to the Portland Association of Teachers, whichever is less. Eddie Wang, chair of the Portland School Board, says Armstrong made $334,750 as her base salary in the 2025–26 contract year. (Her previous contract included 3% yearly increases. She started at $325,000 when hired in 2024.)

The contract would also provide a retention incentive beginning after Armstrong’s completion of four years of service with the district. If Armstrong completes her service in 2027–28, she will receive a retention bonus in June 2028 of 3% of the base salary in effect that year. In each subsequent year, the retention bonus will be upped to 5% of the base salary.

If approved, the contract will also increase Armstrong’s retirement annuity from 8.5% to 9.5% of her base salary for the current year, and then go up again to 10.5% effective in July 2027. It would nearly double her monthly car stipend from $400 to $750 per month, increase the number of vacation days she can cash out, and allow her up to five flex days for district work she does on weekends or holidays.

The district did not immediately respond to a request for comment.

Wang tells WW that understanding the contract requires additional context. He says that Armstrong advocated for an additional provision to match PAT’s cost-of-living adjustment because her yearly 3% increase had made her “uncomfortable.”

“She’s actually asking for COLA decrease,” Wang says.

Wang adds that despite being the largest school district in Oregon, Armstrong’s total compensation package lags behind similarly sized school districts nationwide, and local districts like Beaverton.

The superintendent, he says, more so hoped to prioritize her time in the current round of contract negotiations.

“The thing that she asked for that I think was more important to her than pay was respect of her personal time,” Wang says. “For example, she was spending a lot of her vacation time doing work stuff...adding five flex days is just a recognition that she doesn’t get as many vacation days as she was promised in the original contract.”

The timing of the extension comes as the district braces itself for another round of budget cuts, with a $65 million shortfall expected in the spring.

In her third year, Armstrong is planning to take on one of the most politically explosive challenges a superintendent can. PPS is expecting to close between 10 and 20 of its elementary, K-8 and middle schools ahead of the 2027–28 school year.

At the Tuesday Portland School Board meeting, ahead of the board’s vote, Alisha Chavez, the PAT president, delivered a fiery public comment to the board and superintendent.

Chavez said that teachers have been asked to take furloughs and handle larger class sizes in the wake of PPS’s financial crisis, while there’s been room for more compensation at the top.

“Don’t tell us that there is no money for competitive compensation, manageable workloads, and the conditions educators need to stay in this district and students while approving raises, increased benefits, and retention bonuses for the superintendent,” Chavez said.

She added that while this package makes Armstrong’s compensation comparable to other superintendents, other local districts do not have management teams the size of that at PPS.

And Chavez issued a warning for the union’s upcoming contract negotiations.

“We will remember the choices you make when we sit across the bargaining table from you all,” Chavez said. “We are asked to sacrifice while those at the top are protected. This is not shared sacrifice, and it is not sustainable.”

This story has been updated.