He’s climbed quickly and moved often. Can Baltimore schools’ new CEO make lasting change?

PHILADELPHIA — Jermaine Dawson bounced between his laptop and a marker-dotted smart display in his office as he explained the world of data that exists inside of his head.

The former math teacher tracks where every high school senior in Philadelphia is going after graduation and how much scholarship money they’ve acquired. As the deputy superintendent of academic services, he records how often the administrators under him visit classrooms, down to the time of day they show up. A presentation on Philadelphia’s rising test scores ends on his personal philosophy: “In God we trust. Everyone else must bring data!!!!”

Over a two-decade career spanning six cities, Dawson has built a reputation for obsessively tracking student achievement. Administrators in the school districts where he’s worked credit him with pinpointing problem areas and laying the foundation for academic improvement. But in large, slow-moving school systems, it takes years to see results, and Dawson has rarely stayed in one place for long.

His next landing pad is Baltimore, where on July 1 he’ll become the CEO of the city’s 76,000-student public school system, fulfilling his long-held ambition to become a superintendent. Not one of the nearly 20 current and former colleagues The Banner interviewed were surprised he’d snagged the gig; he’d almost done it before in three other districts.

But Dawson is a novice, untested in the top job. He’s managed large budgets and thousands of employees but has little experience answering publicly for the controversial decisions required to fix complex problems. A city newcomer, he’ll have to navigate tricky political forces, corral billions for the budget, negotiate union contracts and close schools — all while building on his predecessor’s decade-long work of boosting student test scores.

Dawson will replace Sonja Santelises, who’s led the district since 2016 and in that time stabilized its finances, reduced turnover among principals and improved academics. She leaves Dawson with a school system that still lags behind the state in test scores and faces complex issues at the intersection of school choice, enrollment trends and transportation.

Dawson, whose public school education and years in the church guided him through an impoverished Atlanta childhood, said he sees himself in Baltimore’s kids.

He will be a leader hyperfocused on academics and making sure kids have what they need to succeed, said Reginald Streater, president of the Philadelphia school board.

“You’re not getting a business-minded CEO, which some people believe public education needs. You’re getting an actual educator,” Streater said.

Dawson is not intimidated by the prospect of running a large urban school system for the first time. He’s excited.

“I like to take on challenges head-on,” said Dawson, 51. “I like to lean into the struggle, if you will, and take it by the horns, and work with the team to get it done.”

A ‘fireball’ from tough beginnings

Dawson commands a room with the charisma of a youth pastor.

He’s had that confidence since the 1990s, when Sharon Hawkins Gay met him as a swaggering Atlanta teenager.

“He had a presence, even then,” said Gay, who taught Dawson advanced biology and now considers him her son. “He seemed wise beyond his years. He was like an old soul in a young person’s body.”

Dawson’s confidence masked a tough childhood. He spent his earliest years without a permanent home and recalls sleeping on porches and eating out of trash cans.

Faith became his refuge. His pastor and church family helped get Dawson and his siblings into a housing project. His late mother worked multiple jobs to keep them afloat.

“He ended up at the church, and he was a buoyant, happy, upbeat kid, and he was there all the time,” said James K. Whitely, a lifelong friend and pastor. His faith stuck: Dawson was once the pastor of a small church in Atlanta and still ministers today, though he declined to get into the details. He’s not trying to convert anyone, he said.

Dawson had a knack for finding mentors who have supported him throughout life. Whitely and his wife gave Dawson an old car to take to college. Gay and other teachers crowdfunded money to send him to Senegal for a foreign exchange program.

John Holley, who taught Dawson in a program for high schoolers to learn leadership skills and self-esteem, said Dawson was a “fireball” and always the first to volunteer. Dawson met Maynard Jackson, the first African American mayor of Atlanta, through that program and went on to attend the historically Black Morehouse College at Jackson’s encouragement.

Dawson stayed close with Gay through college, mentoring kids at the elementary school where she had become principal. In an NBC news segment about his volunteer work, Dawson shared the same motivation for educating kids then as he does today.

“I realize where I’ve come from,” the younger Dawson told NBC. “I know what it is to not have food. I know what it is to not have clothes.”

Dawson went on to work as a math teacher under Principal Gay. Decades later, Gay fought back tears as she watched the Baltimore school board unanimously vote Dawson into the district’s top job.

“From the very beginning, I said, ‘You’re going to end up being a superintendent one day,’” Gay said. “I said, ‘I want you to do it, I want you to pursue it.’ And look what happened.”

A man on the move

After climbing from teacher to principal in Atlanta, Dawson started crisscrossing the South. He held five jobs between 2014 and 2020, moving from Houston to Birmingham to Jacksonville to Orlando and back to Atlanta. He returned to Birmingham for three years and has been in Philadelphia nearly as long.

Dawson said the many moves helped him gain experience and build a résumé. But most administrators don’t move around so frequently, said Rachel White, a University of Texas at Austin associate professor who studies superintendent leadership.

Such frequent job changes make it difficult to judge whether Dawson made lasting impacts in one place. School administrators can rarely do that in two or three years, White said — real changes in learning “are the product of something that’s deeply rooted.”

“A school system is like a cruise ship, not a fishing boat,” said White. “To change the direction of that system is going to take more space and time, just like a cruise ship takes more space and time to turn left than a little fishing boat.”

But educators across the country insist Dawson made a difference in their schools.

Dawson, who describes himself as a humble man, said superintendents have called from “all over” asking that he bring his expertise to their challenged schools.

Birmingham Superintendent Mark Sullivan said Dawson was the first person he called when building his team, compelled by Dawson’s work in multiple districts and his personal story. Dawson established consistent teaching practices across classrooms, Sullivan said, which was important for the city’s large number of transient kids who need steady instruction as they move between schools. Kids move a lot in Baltimore, too.

“We’ve seen some major improvements, even beyond where we were before the pandemic,” Sullivan said, “and really, we attribute a lot of that to him kind of kicking us off.”

Sullivan said the district recently received its highest grade ever on the state’s annual report card and has significantly reduced its number of “F” schools.

Richard Franklin Jr., president of the Birmingham teachers union, said Dawson transformed the culture there: “We have turned into perfectionists. We are not failing anymore, and we have a standard.”

Streater, Philadelphia’s school board chair, said Dawson “understands how to use data in an empirical, qualitative and quantitative way to be able to make the case to educate children and to support the mission.”

“You don’t find people like that every day,” Streater said.

Though Dawson has held high-level jobs, he’s largely worked behind the scenes, facing little public criticism.

But even teachers unions, which often spar with administrators, praised Dawson’s open-minded and collaborative approach.

Franklin said Dawson always acknowledged the work of Birmingham teachers when he spoke.

“I can’t think of one time when we approached him and he wasn’t receptive,” Franklin said. “We had conversations that were uncomfortable, but we made the best decisions for our families and our students.”

In Philadelphia, former academic leaders had contentious relationships with the union driven by ego, said Arthur Steinberg, president of the Philadelphia Federation of Teachers. But not Dawson.

“He treats the people with the respect and dignity that they deserve,” Steinberg said.

Ready to listen — and dazzle

Rarely has Baltimore welcomed a new school leader with such fanfare as it did Dawson.

Last month, Mayor Brandon Scott and City Council President Zeke Cohen attended the school board’s vote to hire Dawson, who was accompanied by family and supporters. Everyone made speeches.

Dawson then toured schools, met with Santelises and was introduced around town. He greeted everyone individually, which often made him late to his next events. When Dawson learned that a high school senior was headed to his alma mater for college, he insisted on meeting him.

“I know what it is to have people in high positions — presidents of the United States, mayors, people like that — who were mentors in my life, who didn’t have to take time for a little old boy from the projects,” Dawson said. “But they did. And that has carried me into how I approach people in life.”

Dawson talks openly about many personal aspects: his wife, whom he calls his boss, and his rising sixth grader, who will attend a Baltimore public school.

But Dawson volunteers much less about his work in the church, even declining to name his denomination.

Still, when he spoke to groups of students in Baltimore, Dawson could have been standing at the pulpit. He leaned into call-and-response and often spoke in analogies, like parables. He told kids he’s a “living witness” that education can change your life.

On classroom visits, he got eye-level to talk to students and sat next to them during lessons. He repeated the same stories and jokes.

While Dawson was on a tour to impress, things were heating up back in Philadelphia, where City Council members threatened to withhold funding over a plan to close 17 schools. Dawson will confront the prospect of school closures again in Baltimore, this time as the public face of the unpopular process.

Clifford Jones, now a South Carolina superintendent who worked with Dawson in Georgia, expects him to be a “hard-charger” who will not be afraid to increase expectations.

“Transformation is not an easy gig,” Jones said. “You have to push for things.”

Dawson expects to make hard decisions and said that all good leaders come with battle scars. But he intends to start his tenure in Baltimore by listening.

“Because even though I have experiences in other places,” Dawson said, “none of these places are Baltimore.”

About the Education Hub

This reporting is part of The Banner’s Education Hub, community-funded journalism that provides parents with resources they need to make decisions about how their children learn. Read more.