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Oakley ascends in district that educated her, sharing a national spotlight at a critical time

When you grow up to become a leader in your own community, it’s a community accomplishment. That’s what Whitney Oakley is learning. It’s what she wants to teach the children in her district, too. 

Oakley became the first Guilford County native appointed as superintendent on Aug. 31.

“Guilford County Schools is a very special place for me, and I know it is for you, too,” Oakley said at her installation ceremony. “It is where I decided to raise my family and dedicate my career. Having grown up in Guilford County and now a parent to two GCS students, I have a unique vantage point of where we have been, where we are today, and where I see us headed in the future.”

Oakley’s mother, Sheila Polinsky, isn’t surprised to see her daughter lead one of the nation’s 50 largest districts. She says she saw leadership qualities in her since she was a toddler. 

Those who knew her daughter as a child aren’t surprised, either. Just the other day, Oakley’s seventh-grade piano teacher, Charlotte, tracked down Polinsky upon hearing the news. 

“She remembers having conversations with Whitney during a piano lesson about how important education was,” Polinsky said. “And when Whitney told her she wanted to be a teacher, Charlotte said, ‘Or you can be superintendent.’”

As superintendent now, Oakley will lead a district that has often existed in the national spotlight, and that today confronts both opportunities and challenges.

A district accustomed to the spotlight, that’s in turn spotlighting equity

On Monday, first lady Jill Biden and Secretary of Education Miguel Cardona made Guilford County one of 10 stops on a nationwide back-to-school tour. It’s the third time the White House or Department of Education has recognized the county recently, but the spotlight has been on Guilford for decades.

“Some of it, I think, is the result of it being a community that has rural, suburban, and urban all in one district,” said Mo Green, who was superintendent from 2008-2016. “So it’s one that you can look to and really get a sense of progress that students are making and really look across a community that has all of that in one community.”

Much of the attention the district has received is for initiatives that promote equity. Indeed, that’s how the district — as it exists today — captured the national spotlight from its inception.

The current iteration of Guilford County Schools evolved from a merger of three different school systems in 1993. Prior to that, Guilford County Schools sat separately from the High Point and Greensboro city school systems in a highly segregated education ecosystem. 

In 1983, when merger discussions begun, Oakley was just three years old. A poll in the local paper said a majority of residents opposed the plan. The superintendent of Charlotte-Mecklenburg Schools, which consolidated 24 years earlier, visited Guilford to tell residents why it was important.

If not for the merger, then-CMS Superintendent Jay Robinson said, “we’d have had a black city school system and a white county school system.”

Whitney Oakley's graduation certificate after completing second grade at the K-2 Guilford Primary School in 1988.
Guilford County Schools Superintendent Whitney Oakley’s graduation certificate from Guilford Primary School. Courtesy Sheila Polinsky

Oakley was receiving her own education on why that would be a bad idea. Both home and school immersed Oakley in an environment of inclusion. At four years old, she walked onto the campus of Guilford Primary School for her first day of kindergarten. Today, it’s the Doris Henderson Newcomers School and helps refugees and immigrants transition to American schools. 

Guilford County Schools Superintendent Whitney Oakley in elementary school. Photo courtesy Sheila Polinsky

When the principal it’s now named after led it, it was a K-2 school. Even then, it hosted students from 49 nationalities and started with belonging. Literally.

“When we would get off the bus, even on the first day of school, Dr. Henderson knew our name,” Oakley remembers. “And it just meant so much to me. School felt like home. And so I’ve always wanted to make sure that school feels like a safe place for our kids.”

Oakley makes plans as Guilford County Schools doubles size 

When Greensboro City and High Point City Schools merged with Guilford County Schools in 1993 to form the third-largest school district in North Carolina, it bucked the trend of city districts splitting off to form smaller systems. The new district helped further desegregate Guilford-area schools. In a county home to the Greensboro Four, desegregation was a flashpoint issue. The country watched to see what would happen.

The national press voiced approval within a few short years, quoting those who opposed the merger as welcoming the better, safer schools. And the district was innovating — opening the state’s first middle college and early college high school programs. Observers from both within the district and outside credited long-term planning and nimble pivots along the way for the successful merger

Oakley was just 12 when the merger happened, transitioning from Guilford Middle School to Ragsdale High School. She was already practicing those planning and pivoting skills, though — experience present moments while also planning for the future.

“It went something like this,” Polinsky said. “I know what we’re doing today, but what about tomorrow? She was spontaneous, she could be, but she wanted to know, what’s the plan for tomorrow?”

At 16, already a high school graduate, Oakley made three- and five-year plans before heading to East Carolina University. She knew she wanted to teach and began her higher education working on that goal.

While in college, Oakley attended a party where a friend was the DJ. There, she met a group of adults with intellectual disabilities — the experience touched her.

Oakley shuffled her college plans to add a focus on special education during her studies. 

“I think that’s part of the focus — let’s focus on what we need to do right now, but have a longer-term plan so that we can work towards that, too,” Polinsky said. “But we have to get through today before we can do three years from now.”

Doris Henderson observes a class at the school that is named after her. Rupen Fofaria/EducationNC

A growing divide around politics and schooling

When Oakley was growing up, her mom didn’t pay much attention to school board activity.

“I hear younger parents talking about ‘We’ve got to make sure we get the right person on the school board,'” she said. “I never gave it a thought.”

Today, heated debates are common at school board meetings — with lines of parents showing up to speak out.

“We’re at a time where we’re going through a very contentious period in our political history — in the county, in the state, in the United States,” said Sharon Contreras, a woman of color who resigned as Guilford County Schools’ superintendent because, she said, she worried someone might harm her or her son.

Last year, members of a local conservative coalition in Guilford County gathered to protest during a school board meeting, according to a report from Triad City Beat. The Board had closed the meetings for in-person attendance, having moved to streaming during the pandemic. Protestors banged on the windows and shouted that they wanted to “take our power back.”

In response to a records request for submissions to the district’s “Let’s Talk” messaging platform, Triad City Beat also found a number of personal threats against Contreras, many of which were racist in nature.

That’s the climate Contreras left and Oakley enters. But Contreras has watched Oakley grow into her leadership and believes Oakley is the right person for this time.

Oakley possesses a rare combination of inherent disposition and acquired skills, says Contreras, that make her uniquely suited to address both the quality of schooling and the information flow. Her experiences as a young person helped set her disposition. She developed the skills over decades in education — as a teacher in Guilford County, an administrator in Alamance-Burlington School System, and in serving the past 10 years in Guilford County Schools’ central office. 

Oakley served many of the last 10 years under Contreras.

Studying strong leadership and developing her own

Contreras was a nationally recognized superintendent who landed on the short list for President Joe Biden’s Secretary of Education. Hers are big shoes to fill. But Contreras says Oakley has the ability. She recognized that almost immediately — even though, as she reflects, she easily could have missed the rising star.

“Guilford County has sort of a small town feel, but the district is massive,” Contreras said of the 10,000-employee system. “There are many, many layers to the district. You know, it’s remarkable that I met Whitney that first year.”

When she did meet her, Guilford County Schools was transitioning from balanced literacy to instruction grounded in the science of reading — four years before the state would pass a law mirroring the switch. And Oakley led much of that effort, something that Contreras and Oakley bonded over quickly.

In fact, some of that began before Contreras arrived. Green, who was Contreras’ predecessor, remembers Oakley’s work ethic and demeanor as breeding confidence in what she said. He remembers asking her to present directly to the school board on reading curriculum, and how effective she was at communicating strategy.

But away from the podium, Contreras remembers a softer presence from Oakley.

“She was very quiet, almost fearful to speak,” Contreras said. “As I pushed her to talk to me about the work she was doing, I learned she was a wealth of knowledge and just incredibly smart.”

Contreras said she knew she’d found a special talent, and she also knew she’d need Oakley to execute her vision for moving the district forward.

“Whitney wasn’t one to promote herself at all,” Contreras said. “There’s some people who do that — in fact, there’s lots of people who do that. But that wasn’t Whitney at all. Whitney just does the work and she’s very, very supportive of leadership. I really came to respect the way she worked hard to support the district and support leadership — not because she wanted to win over the leader, but because she understood that if the leader isn’t successful, children are not successful.”

Guilford gains ground while Oakley hones her skills

Under Contreras’ leadership, the district increased funding for teacher and leader development by millions of dollars, instituted three assistant principal development programs, and revamped coaching for teachers in literacy and math. The district has long led the state in graduate rates, but this past year, the district posted a record-high graduation rate of more than 90%.

Twice this past year, Guilford received national attention for its pandemic response. It received an Excellence in Education Data Award from Harvard University for its use of data to respond to student needs during the pandemic. Last month, the Department of Education highlighted the district and its use of relief funds for tutoring programs.

“It was an honor to work and learn from Dr. Contreras, a transformational and visionary leader,” Oakley said at her installation ceremony. “I am grateful for her numerous contributions to our community.”

Guilford County Schools then-superintendent Sharon Contreras ties the shoes of one of the Southwest Guilford Elementary School students on the first day of class on August 23, 2021. Chris English/Tigermoth Creative

Oakley played a critical role, Contreras said, and did it at a time when attitudes toward public schools are tenuous. It’s also a time when the district and local economy are coming into some serious dollars.

“You need someone who understands the county and can continue to try to work with all of the constituents,” Contreras said. “She has earned this position.”

She earned it, in part, by helping Contreras navigate to the dollars that are about to flow in. Last year, Contreras criss-crossed the county touting the benefits of a proposed school bond. County residents voted for a $300 million school bond in 2020 and now there was another for $1.7 billion on the 2022 ballot.

“There was a lot of intentional disinformation being spread in pockets of the community that I was only intending to repair, rebuild, or build new schools in Black communities,” Contreras said. “And that was heartbreaking for me. It’s always heartbreaking for anyone to believe after my 30 year career that I didn’t fight for all children, love and care for all children. But that’s the intent of disinformation — to sow chaos in communities and to ensure division.”

Contreras turned to Oakley for help. 

“Whitney would go out to those churches and she would go to those community members and she would speak to groups of women that look just like her and say, ‘You’re being lied to. This isn’t true. I work with the superintendent every single day and here are the facts,'” Contreras said. “And she would get those votes for that school bond one by one.”

Leading in a new era

The new school bond — the largest single school bond in state history and third-largest in the country, according to Contreras — isn’t the only thing that makes this a unique time for Oakley’s appointment.

In the past year, several companies announced a move to Guilford County and the surrounding area. Boom Supersonic, maker of high-speed jets, is coming this year, beginning production in 2024. Last year, Toyota announced plans to build a new factory for electric vehicle batteries. 

“Businesses and families are already moving to Guilford County because of the quality of education we provide,” Guilford County School Board Vice Chairperson Winston McGregor said at Oakley’s installation. “Dr. Oakley is the right person at the right time to lead GCS through our next chapter.”

Whitney Oakley reads to students at the Doris Henderson Newcomer School in Guilford County. Rupen Fofaria/EducationNC

Oakley will play a key role in using the school bond money and setting the district up to fill the incoming jobs and attract the future jobs. And for that, she’s already started to plan.

“The next decade is the most consequential decade for our children and community,” Oakley said. “It will take all of us working together to succeed. In the coming days, we will be launching a series of community conversations to envision our shared future for students, families and community.”

How she’ll chart her course — with inclusiveness at the center

As Oakley works on plans — for addressing achievement gaps, for diversifying and bolstering the teacher workforce, and for maximizing the money residents voted to spend on schools — she’s hyperaware of the challenges. She knows there’s some division in the county, as there is across the state and country. She knows that legislators and policymakers in Raleigh are making decisions that will impact her workforce. 

But she has the ability to plan for those things while she focuses on what’s before her.

Polinsky laughs when she talks about Oakley’s level of focus. She remembers a day when her daughter, in kindergarten at Guilford Primary, came home frustrated. She pulled a paper out and said she had to do her work all over. The assignment: color some grapes. The very limited instruction: color within the lines. But Oakley had scribbled her coloring all over the page.

“And I was surprised because she’s compliant, you know, a rule follower — indignantly sometimes,” Polinsky said.

Whitney Oakley, left, sits with her first principal, Doris Henderson. Rupen Fofaria/EducationNC

She saw her daughter’s frustration and had her sit in her lap. She sat with her while Oakley re-did the assignment. And so they sat, daughter in mother’s lap, and Polinsky watched as Oakley meticulously colored in the grapes. She included shading and colored some grapes lighter than the others.

“Some of the grapes are not ripe yet,” Oakley told her.

Polinsky marveled at the job, but she wondered — what happened the first time?

“I went to school to read, I didn’t go to school to color — I’ve already done coloring,” Oakley told her.

It’s the first story Polinsky thinks about when she reflects on her daughter becoming superintendent. It reminds her that her daughter can get the job done, but that she’s always got an eye on what’s next.

“She has the ability, not just the words,” Polinsky said. “She has the ability to focus on what’s important.— what’s first and foremost. And keep that focus.”

Oakley can move on to trying to unite a community and working with policymakers. But she’s not going to lose focus, she says, on what she believes is her first priority.

“I go back to the promise of public education and we believe very strongly that Guilford County Schools is a great place to work and to learn and to grow,” Oakley said. “Businesses are moving here at an unprecedented rate and it’s because we do a good job of educating our kids. My takeaway from that is … we have one main job and that’s to educate our children in a place where they feel safe. And that’s what we’re primarily focused on.

“We hope our laws and policies fall in line with teacher compensation, bus driver wages, all of these things are critically important to help keep us going. But we also have to keep teaching and learning our core business.”

Sitting with her first principal on the day before she was named superintendent, Oakley reflected on where that core priority was born. It was Henderson who planted that seed in her. 

“What we can learn is that public education is a place where everyone belongs,” she said. “We take everybody.”

And Henderson beamed right back, holding the hand of that same girl she first met at four years old.

“I feel like Guilford County is in good hands,” Henderson said. “Just hearing her talk, it makes me feel good about the children in the schools.”

Rupen Fofaria

Rupen Fofaria was the equity and learning differences reporter for EducationNC from 2018 through October 2023.