Overseeing one of the largest school district bus fleets in the entire country is no small feat, but Kimberly Jones tackles the task with poise, purpose, and passion — and a heavy dose of innovation and strategy.

Jones has been the executive director of student transportation services for Chicago Public Schools (CPS) for five years. Prior to that, she worked in public transit at Greyhound Lines and as a fitness manager.

A product of Chicago Public Schools herself, Jones saw an opportunity to make a difference in the lives of students in her own neighborhood.

“Greyhound really taught me some things here in Chicago,” she reflected. “I was charged with turning the terminal around. That role provided extensive experience in managing large-scale operations, implementing strategic planning, and navigating the complexities of a fast-paced transportation environment. I learned to build and strengthen both internal and external relationships, a skill that continues to be essential in my position now.”

Jones applies strategic planning principles to much of her work now, from optimizing routes, improving vendor relationships, enhancing safety protocols, and driving positive outcomes for the students the district serves.

A Look Inside the Large Operation

CPS outsources its transportation, working with about 20 contractors for general route and paratransit service. Among the providers are First Student and First Alt, Illinois Central, AM Bus Company, Zum, EverDriven, and others. On the software side, it uses Edulog and Zonar.

How does Jones successfully collaborate with so many partners? “Maintaining strong relationships is paramount to my success, and is built on a foundation of collaboration and transparency,” she said. “I view my vendors as strategic partners, not just service providers, with open communication, regular check-ins, and continuous improvement.”

Being responsible for such a large-scale operation requires a high degree of skill, but Jones remains humble and gives kudos to her team and partners and credits a collaborative approach for success.

Navigating a Driver Shortage 

Jones began her role as executive director of transportation at CPS just as the COVD-19 pandemic unfolded. At its height, the district lost nearly half of the 1,300 bus drivers needed, plus aides and nurses.

It takes a multi-faceted approach to reach success after a major disruption, and Jones got to work. 

To start, she structured transportation in priority groups and helped revise CPS board policy to ensure that students with disabilities, students experiencing homelessness, and those from lower-income backgrounds, never lost access to education. 

She also negotiated a historic collective bargaining agreement with the district’s labor partners to increase driver wages, upped recruitment, hiring, and marketing, implemented retention bonuses, advocated for the "Under the Hood" waiver, collaborated with the state of Illinois to expand accessibility for CDL testing in additional languages, and added new contracting partnerships.

“Despite these unprecedented challenges, Kim's leadership was crucial in stabilizing operations, enhancing efficiency, and restoring essential transportation services amid a nationwide driver shortage,” said Charles Mayfield, the district’s COO. “These initiatives have made CPS a more competitive employer, leading to improved service reliability and increased workforce morale.”

In 2021, CPS had 624 drivers, increasing to 738 in 2024, and 895 now. “That's definitely a step in the right direction,” Jones said, “and addressing the driver shortage has been my top priority.”

Serving Vulnerable Students

If it’s not apparent already, Jones has an unwavering commitment to student access and equity.

Mayfield shares that Jones upholds the Illinois State Board of Education’s guidance, ensuring that students with disabilities experience travel times within the 60-minute limit. 

Additionally, the growth in driver workforce that Jones spearheaded enabled a system of student transportation hubs. Through restructuring efforts, Jones restored bus service for 1,397 general education students who had previously been without transportation.

She also manages approximately 1,500 public transit passes for students and their companions, ensuring that all eligible students have equitable access to safe, reliable transportation.

“Transporting students with disabilities or those experiencing housing instability is a responsibility that we take very seriously, requiring a specialized and deeply compassionate approach,” she said. “For us, it means prioritizing our most vulnerable students, ensuring they receive services first.”

“Her ability to balance operational constraints with student-centered solutions has been critical in maintaining access to education, solidifying her reputation as a leader in K-12 student transportation,” Mayfield wrote.

Jones’ Approach to Leadership

Naturally with so many students in her care, Jones is no stranger to scrutiny. And though she acknowledges handling it all is no easy feat, she never seems to break a sweat.

Whether dealing with parents, the public, or the media, she believes that most concerns stem from misinformation, unrealistic expectations, resource constraints, and competing priorities.

To counter this, she doesn’t shy away from hard conversations, focusing on proactive and transparent communication. Her approach leads with compassion, always.

“Parents and the public understandably want the best for their children, and so do I,” she said. “We manage these expectations by providing clear explanation of our process and constraints while remaining committed to continuous improvement.” 

Putting the whys behind district policy in publicly accessible spaces is one tactic CPS uses to clear up concerns.

“I can go on and on about my favorite aspects about my job,” she said. “First is the satisfaction of tackling and triumphing through the complex challenges in a large-scale transportation system. There's a real sense of accomplishment in finding solutions and making a positive impact.”

Jones’ service extends beyond her district. She’s also active in local associations and the National Association of Pupil Transportation (NAPT).

What Else & What’s Next?

Soon, CPS is about to embark on a brand-new adventure: owning its own bus fleet. It was awarded $20 million in early 2024 from the EPA’s Clean School Bus program and plans to acquire 50 electric buses for the first time in district history.

“The successful implementation of this initiative will set a new standard for sustainability, efficiency, and long-term cost savings,” Mayfield added, “positively impacting hundreds of thousands of students while positioning CPS as a national leader in sustainable school transportation.”

As one of the first women in this role at CPS, and for so many more reasons, Jones is a trailblazer. “I understand the significance of my position and I don't take it lightly,” she said. “So what truly keeps me motivated is a profound understanding that the work I do and the decisions that I make directly and significantly impact the lives of countless individuals. I play a very important role in the future of our students.”

When Jones isn’t strategizing over how to serve more students or planning for new fleet additions, she relaxes by crafting, a good game of Monopoly, and spending time with friends and family, including her children and grandchildren. She also takes pride in doing community service alongside her sisters in the Order of the Eastern Star.

She also admits that it can be lonely at the top, especially when she has to make difficult decisions. And, she still learns something new every day.

For future leaders, she advises them to get comfortable being uncomfortable, block out the noise, and leave no stone unturned when doing what is best for students.

Just like she does every day.