The School Superintendents Association (AASA) has chosen its four finalists for the 2025 National Superintendent of the Year Award.
AASA announced on Monday that the four finalists were chosen based on their exceptional leadership skills and dedication to furthering public education in their local communities. Each superintendent was nominated by their respective state association as winners of their state superintendent of the year award. The judging criteria included communication, professionalism, community involvement, and creative leadership strategies to positively impact students and meet their educational needs.
The four finalists are Sharon Desmoulin-Kherat of Peoria Public School District 150 in Illinois, Walter B. Gonsoulin, Jr., of Jefferson County Schools in Alabama; Debbie Jones of Bentonville School District in Arkansas, and David K. Moore of School District of Indian River County in Florida.
“These extraordinary leaders embody the transformative power of public education,” said AASA Executive Director David R. Schuler in a statement. “Their visionary leadership is creating dynamic opportunities for students, uplifting communities, and advancing the promise of public education as the foundation of our democracy. We are honored to celebrate their achievements.”
The winner will be announced during AASA’s National Conference on Education, held March 6-8 in New Orleans, Louisiana.
A $10,000 college scholarship will also be presented to a high school student at the school the winning superintendent graduated from or within the school district the superintendent now serves.
The award is presented in partnership with Corebridge Financial and Sourcewell. Prior sponsor First Student is no longer aligned with the award but remains an exhibitor at the AASA along with a half dozen other companies aligned with the student transportation industry.
An empty high school classroom. (Dan Forer | Getty Images)
Department of Public Instruction Superintendent Jill Underly, who is running for her second term in office with the backing of the Democratic Party of Wisconsin, faces a challenge from Sauk Prairie School District Superintendent Jeff Wright, a Democrat who says he wants to improve DPI’s communication.
Elections for the state superintendent are technically nonpartisan. Candidates run on the same ballot in the February primary, and the top two advance. The primary is Feb. 18, 2025 and the general election is April 1. No other candidates have entered the race so far.
Underly won her first term in a landslide in 2021, defeating her conservative opponent, a retired superintendent backed by Republican-leaning groups, in a campaign cycle where a record $3 million was spent on the race by candidates and outside special interest groups.
In her September campaign announcement, Underly highlighted some of her accomplishments, and said that students and staff need to be supported in Wisconsin.
At the helm of the agency, Underly has advocated for increased investments in public education in the state budget, including for special education funding, mental health resources, staff pay and more. She recently announced a budget request that would dedicate an additional $4 billion in state funds to public education. The DPI under her leadership also helped shape a law that reforms the way reading is taught in Wisconsin schools, though the Legislature has not released the money to support the changes despite Underly’s multiple urgings.
Jill Underly, State Superintendent of Public Instruction (Photo courtesy of Underly)
Underly also highlighted the ongoing politicization of schools in her statement. Throughout her tenure culture war issues have continued to divide voters at the state and local level and she has been an outspoken critic of efforts to cut diversity, equity and inclusion programs and to target LGBTQ+ staff and students.
“I’ve fought for kids and their teachers to be their true selves in school and stood up to ensure they see themselves represented in their curriculum and in their libraries,” Underly said in a September statement announcing her reelection campaign. “In a second term as superintendent, I want to make sure we continue to make necessary investments in our kids, as well as continue to examine how we evolve education to meet the challenges of the future.”
Prior to winning her first term in 2021, Underly served as the superintendent of Pecatonica School District, a rural district in southwestern Wisconsin. She has also previously worked as a principal, a teacher and a state consultant to Title I schools in Milwaukee and across the state.
Wright, who launched his campaign about a month after Underly, has served as the superintendent of Sauk Prairie School District since 2019 and was named Administrator of the Year in 2024 by the Wisconsin Rural Schools Alliance. He also previously served as a principal in Chicago. He hasn’t held public office before, but has run unsuccessful campaigns in 2016 and in 2018 for the state Assembly.
Wright said in an October interview with the Examiner that he probably aligns closely with the current superintendent on many issues, but he thinks there is currently a “disconnect” between DPI and schools.
“They’re not bringing the people together from the teachers’ union, the administrators’ associations and other groups to have an active conversation about what concrete steps are we taking right now to get this work done,” Wright said. “Schools want to know what’s happening at the DPI. We don’t want to be surprised by changes. We want to be in conversation so that it’s very clear that we’re working on the same team.”
Wright cited concerns about whether enough effort has gone into recruiting and retaining educators. He said that he’s also heard “palpable frustration” from educators about the change to standardized testing scores and the lack of communication with school districts about it. The agency lowered the proficiency threshold and changed the terms that are used to to describe student performance, which critics said made it difficult to make comparisons to previous years.
Sauk Prairie School District Superintendent Jeff Wright. (Photo courtesy campaign)
Wright said that he would set himself apart from the current administration by trying to minimize partisanship. He said his district has tried to do this “by making sure that we’re listening to everyone and that we make sure that our doors aren’t closed to people, regardless of their opinion, especially if their children are in our schools.” He said that he hopes “it would also allow for more open conversations with legislators of all political stripes.”
Wright noted that DPI wasn’t invited to testify to the JFC during the last budget cycle.
“That hurts the DPI. It also hurts public education when we’re not having that open conversation between the agency charged with leading public schools and standing up for them and the legislators who are creating the budgets that do need to be rewritten,” Wright said. Underly did address lawmakers in person at one of the public hearings held by the committee in Eau Claire, but DPI was not invited to make its budget presentation to the Joint Finance Committee during the last budget process.
Wright said schools are also facing challenges as the current funding formula, including for special education, has made it difficult for schools to keep up with costs. He said that funding going to voucher schools “worries” him as well because “there aren’t enough resources for public schools at this point.”
Early supporters of Underly and Wright
Wright has said he was encouraged to run by educators and education professional associations. He did enter the race with a notable supporter — the Wisconsin Education Association Council (WEAC) Political Action Committee.
The Wisconsin Education Association Council is the largest teacher’s union in the state, and its PAC, which aims to help elect “pro-public education” candidates to office, recommended Wright in the race. However, the endorsement process for the full union is ongoing, and it’s unclear when or if a full endorsement will come from the board.
WEAC spokesperson Christina Brey said the PAC’s recommendation is one part of the lengthy endorsement process and said she couldn’t comment on specifics.
“WEAC is in the process of exploring the candidates for state superintendent, and its political action committee has recommended its support of Jeff Wright; however, the process is still ongoing, with no determined timeline on whether or if a decision will be reached,” Brey said.
When asked about the specifics on why the PAC recommended Wright, Brey said she couldn’t comment. She also said she couldn’t speak to the relationship between Underly and the union over the last four years due to the ongoing endorsement process.
Brey told the Examiner that when it comes to the superintendent race, Wisconsin educators are looking for strong and bold leadership and someone that cares as much about students as teachers do. She said some of the issues at play include figuring out how to keep teachers and support staff, how to address the workplace environment, how to handle challenging student behaviors and how to address school funding challenges. She said members will be looking at many things, including policies that have been enacted over the past few years, how those policies have “shaken out” in the classroom, where candidates fall on those issues and who they think will be the best listener, advocate and partner.
Other Wright supporters, according to campaign manager Tyler Smith, include Jim Lynch, Executive Director of the Association of Wisconsin School Administrators. Lynch told the Examiner in an email that the association’s process for endorsing candidates for state superintendent doesn’t begin until later this month, so he couldn’t speak for himself or the association until after the process.
Smith also named the superintendents of Mauston, Reedsburg, Stevens Point and Poynette school districts and the principals of Sauk Prairie High school and Sun Prairie School Board president as supporters.
Meanwhile, the Wisconsin Democratic Party endorsed Underly for a second term at the end of November. Party Chair Ben Wikler called her a “steadfast advocate” for students, parents and schools in a statement.
“From fighting to give rural school districts a seat at the table, to expanding mental health services in schools, to ensuring every school, teacher, and student has the resources they need to succeed, Dr. Underly is the proven leader we need championing our kids in the Department of Public Instruction,” Wikler said.
“At every step, Dr. Underly has had the backs of our kids, standing up to attacks on public education, libraries and LGBTQ+ youth, and ensuring that partisan attempts to divide Wisconsin do not undermine our state’s fundamental and uniting commitment to great public schools, available to all,” Wikler continued.
The state party’s endorsement prompted a strong response from Wright, who said it represented party “insiders” deciding to “ignore” the voices of teachers, administrators and other stakeholders and settling “for the division and mismanagement that have marked Superintendent Underly’s tenure, ignoring failures that are isolating DPI from discussions about the future of Wisconsin’s public schools.”
“Party leaders even ignored the voices of organized educators, a key member of the Democratic coalition, in making this endorsement,” Wright said.
The endorsement process for the state party was launched by two county parties — Waukesha and Milwaukee. Waukesha County Democratic Party Chair Matt Mareno said in a statement to the Examiner that the party was proud to put Underly’s name forward for the endorsement.
“We stood with her when she first ran, and in the years since she’s stood with us shoulder-to-shoulder as we’ve faced down far-right attacks on our public schools,” Mareno said. Schools in Waukesha County have dealt with a number of issues in recent years including becoming the target of a bomb threat and a threatened school shooting after a right-wing social media account publicized posts made by a local middle school principal, as well as books and songs being banned from schools.
“From book bans to bomb threats inspired by right-wing influencers, our community and schools have been through a lot,” Mareno said, “and Jill Underly has been there with us at every step fighting for a better future for our kids.”
BOSTON, Ma. – Mayor Michelle Wu and Boston Public Schools (BPS) Superintendent Mary Skipper today announced two new improvements to ensure BPS’ transportation experience is safe, reliable and on-time for students, families and workers. Building on efforts to improve the daily yellow bus transportation experience for approximately 23,000 students and their families and modernize its operations, BPS has awarded a three-year contract to Zūm. With this new contract, BPS will use Zūm’s technology platform for the upcoming school year district wide which will provide Boston families with improved real-time bus tracking and enhanced communication and transparency about their student’s bus.
Mayor Wu also announced the opening of the new City Academy training facility in partnership with UMass Boston. Located at UMass Boston, the facility will be used to train participants in City Academy’s Commercial Drivers License (CDL) track, support the training of BPS school bus drivers and a new CDL water utilities track. These announcements demonstrate the City’s ongoing commitment to improving transportation for students and families through the use of new, state-of-the-art technology and eliminating barriers to entry for Boston residents, and the intentionality to grow workforce opportunities.
“We have heard from parents and caregivers that there has to be more information and better communication when it comes to transportation. Safety, reliability, accessibility and transparency should be givens in how we get our students to school,” said Mayor Michelle Wu. “That’s why today we are excited to announce this partnership with Zūm and a brand new City Academy in Dorchester. We know there are many moving pieces to building the best public schools system on the planet and with these partnerships, community engagement and energy, we are making big strides as we head into this next school year. I wish every family a successful preparation in these last few weeks and look forward to welcoming back everyone to a safe, joyful, and successful start to the school year.”
“Implementing this technology will build upon our ongoing work to improve yellow bus on-time performance across the City and provide families with real-time information and communication about their students’ buses location and timing,” said Boston Public Schools Superintendent Mary Skipper. “The BPS Transportation team has already implemented systems and reforms that improved our year over year on-time performance by 2.4 percentage points during the 2023-24 school year. We are confident that Zūm’s technology, which BPS has successfully piloted over the past few months, will allow us to improve our operations and gather comprehensive ridership data to drive our on-time performance higher. Coupled with the opening of the City Academy training facility at UMass Boston, today marks a significant step forward in our commitment to providing accessible, high-quality training opportunities and transportation for Boston families.”
Zūm’s cloud-based technology provides a fully integrated student transportation solution to improve bus operations, reduce student commute times, and track children’s arrival and departure from school while connecting parents, drivers, schools and administrators in real time. Through the Zūm app, BPS parents will be able to view their student’s bus assignment, track their child’s bus in real-time, receive automated delay notifications and ETAs, and monitor their child’s pickup or dropoff status. District administrators and operators with appropriate permissions will now be able to track school buses on a live map from start to finish, and ETAs will be adjusted in real time to account for traffic conditions, road conditions, absent, or delayed students
“We are excited to partner with Boston Public Schools. While Boston Public Schools is the nation’s oldest public school system, it has long been known for leading in innovation when it comes to education and data driven decision making,” said Ritu Narayan, Founder and CEO at Zūm. “With Zūm, BPS will now be able to provide state-of-the-art technology to improve student transportation and experience for students, families, drivers and school administrators. Our solution has made a measurable positive impact in some of the country’s largest school districts, and we are thrilled to bring our single unified technology platform to Boston.”
“Mayor Wu and BPS did a great job with implementing this new bus tracking app,” said Jasmine Mattier, BPS Parent. “The Zūm app is amazing and was a complete step up from the old app. As a parent participating in the pilot this summer, getting real-time information and communication about my child’s location was amazing. Parents will definitely be more at ease this school year with this new platform.”
Zūm’s single integrated technology platform includes routing and operations software, onboard GPS navigation tablets using the Zūm driver app, as well as Zūm’s Parent App. The Parent App will provide Boston families with improved real-time bus tracking and enhanced communication and transparency about their student’s bus. Families can learn more and download the Zūm Parent App on the BPS Transportation website. If you are a BPS parent or guardian, you can download the Zūm App at app.ridezum.com and prepare to see your student’s bus assignment and track their rides starting this fall.
BPS joins a growing number of innovative school districts that have partnered with Zūm to leverage Zum’s transportation services and technology platform, including Los Angeles Unified School District, San Francisco Unified School District, Seattle Public Schools, Howard County Public Schools, Oakland Unified School District and Metro Nashville Public Schools.
City Academy is an initiative managed by the Office of Workforce Development that provides Boston residents with free training to address labor shortages in targeted fields, while connecting Boston’s diverse talent pool to family-sustaining jobs. The new City Academy training facility will be used to build upon the initiative’s success and train participants in City Academy’s Commercial Drivers License (CDL) track and support. Previously, CDL participants had to travel to Tewksbury to receive training. The new location is easily accessible by public transit, eliminating transportation barriers to entry for Boston residents and improving program recruitment and retention.
“Central to UMass Boston’s mission is to serve as an educational resource for learners at all levels to enhance their skills and advance their careers,” said UMass Boston Chancellor Marcelo Suárez-Orozco. “We are for the city and welcome this opportunity to improve training in this important service area.”
The City Academy facility will also be made available to BPS and Transdev, enabling them to partner and train around 120 drivers annually – addressing a critical City workforce need. Resulting jobs will offer health benefits, retirement security, union membership, and opportunities for pay increases.
“Over the last several years, Transdev has partnered with the BPS Department of Transportation and the City of Boston to ensure that there are enough qualified school bus operators to bring students in Boston safely to and from school each day, while also creating more great career opportunities for residents,” said Jim Folk, Transdev General Manager. “We are very excited about the new training space, which will allow us to efficiently and effectively train both new and veteran school bus operators. This will help ensure that we are well prepared to safely and reliably transport Boston’s students.”
Additional roles that City Academy supports Boston residents in acquiring include critical positions such as Emergency Medical Technicians (EMTs) and for jobs requiring a Commercial Driver’s License and/or Hoisting License (1C/2A classifications) within the City of Boston. These City jobs pay above Boston’s living wage and offer benefits and opportunities for career advancement. Additionally, City Academy prioritizes populations facing barriers to employment, including low to moderate-income residents and returning citizens.
“It will make a world of difference to have the training site in Boston – it will save people commuting time, allow for folks to take public transportation if they need to, and save wear and tear on our personal vehicles,” said City Academy CDL Participant Tremyne Bray. “I am so thankful for all that City Academy has done for me. I am working for J J Trucking and Bray’s Logistics, owned and founded by City Academy graduate Chris Bray). I’ve gotten to work on resurfacing I-95 and I-495 and learned a great deal about trucking and construction. My dream is to start my own trucking company in the near future.”
The City has also partnered with the Boston Water & Sewer Commission to expand City Academy’s CDL training pathway to include a Water Utilities career pipeline. Labor Market analysis predicts that careers in water, wastewater, and stormwater management will grow by over 10,000 positions in the Greater Boston area over the next decade. Through the Water Utilities pathway, City Academy will prepare residents for careers in water utilities, including three entry-level positions at BWSC: Operations Service Repair Person I and II, Special Heavy Motor Equipment Operators I and II. Students will receive their CDL license with tanker endorsement, Hoisting 1B and 2B, and 4E Catch Basin.
“Boston Water and Sewer Commission looks forward to partnering with Boston Mayor Michelle Wu to create job opportunities through the City’s Worker Empowerment Cabinet and the Office of Workforce Development,” said Henry F. Vitale, Executive Director of the Boston Water and Sewer Commission. “The new Water Utilities career pipeline will provide skills training to Boston residents who are interested in a career with the Commission and our partners in the industry.”
City Academy is currently accepting applications. To be eligible, applicants must:
Be a Boston resident
Be 18 years or older
Have a high school diploma or GED/HiSET
Have a valid driver’s license
Meet income guidelines
Be drug-free
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