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 contract will come with a raise.

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 look to 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, increases Armstrong’s base pay from $325,000 a year to $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.

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 the 2027–28 year, 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 up Armstrong’s retirement annuity from 8.5% to 9.5% of her base salary for the current year, and then up again to 10.5% effective in July 2027. It would up her monthly car stipend from $400 to $750 per month, increase the number of vacation days she is able to 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, the chair of the Portland School Board, 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 shutter between 10 and 20 of its elementary, K-8 and middle schools ahead of the 2027–28 school year.

This story will be updated as more details become available.