Taylor sits down for a special extended conversation with STN’s 2025 Transportation Director of the Year Keba Baldwin, director of transportation and fleet services at Prince George’s County Public Schools in Maryland. He talks school startup operations, parent and media communication, AI and autonomous technology, leading STN EXPO sessions, alternative transportation and more.
RENO, Nev. — Every decision a transportation leader makes reaches far beyond the issue at hand, explained Keba Baldwin, the transportation director for Prince George’s County Public Schools in Maryland.
Whether changing a bus route, implementing new technology or making a difficult staffing decision, leaders must consider how those choices affect employees, students, families, and district operations.
During his session Sunday at STN EXPO West conference, Baldwin, the reigning STN Transportation Director of the Year, encouraged transportation professionals to move beyond simply solving immediate problems and instead develop leadership habits that strengthen their organizations over the long term. Drawing on his experience leading one of the nation’s largest school transportation operations, Baldwin outlined several leadership traits that he believes can help directors navigate increasingly complex school transportation environments.
“Our goal for today is just to really understand the decisions that shape your daily operations and the long-term success that you’re looking for,” Baldwin told attendees on Sunday. “Leave out of here with a better understanding, a better playbook of how to do that.”
Baldwin oversees transportation for approximately 85,000 students at PGCPS, which serves roughly 130,000 students outside Washington, D.C. His department includes about 1,400 employees, a fleet of 1,200 school buses and approximately 800 support vehicles. He told attendees that working in transportation departments ranging from 60 buses to one of the nation’s largest fleets has reinforced one lesson throughout his career: Operational challenges rarely disappear as organizations grow. Instead, leaders must learn to adapt their decision-making to increasingly complex systems and larger teams.
“The issues are the same,” he said. “It’s basically how do you scale them up.”
Looking Beyond the Immediate Problem
One of Baldwin’s primary messages centered on what he called “system awareness,” or understanding the ripple effect every decision creates throughout a transportation department. A seemingly simple routing adjustment, he explained, can influence staffing levels, communications with families, training needs and overall public confidence in the transportation system.
“Every decision in your transportation department has a ripple effect,” Baldwin said. “A routing change touches staffing. Your staffing shortage becomes a communication problem. A procurement decision reshapes training. Your technology rollout moves a family’s confidence up or down.”
He cautioned that transportation leaders who focus only on solving the immediate issue are more likely to experience burnout and unintended consequences later.
“The director who only sees that first order is going to get burned out very quick. You have to be able to see it all the way through. You’ve got to play the second, third, fourth order,” he said.
Baldwin illustrated the concept using his school district’s summer transportation planning process. Extended School Year transportation depends on multiple departments meeting tight timelines, while route bidding, dry runs and parent communications all must occur within a condensed schedule. Delays in one department can quickly disrupt transportation’s ability to deliver services.
Baldwin said that same deliberate approach should apply to procurement decisions, which often involve transportation, finance and purchasing departments working together. Rather than rushing contracts or major purchases, he encouraged leaders to understand district procurement processes, carefully review contract language, and build relationships with purchasing and budget officials. Doing so, he said, can help departments avoid costly mistakes while positioning them to take advantage of funding opportunities when they arise.
Building Trust on the Front Lines
Beyond managing budgets and contracts, Baldwin said transportation leaders must remain connected to the people who keep their operations running.
He argued that many administrators describe drivers as “the backbone of the operation,” but said genuine appreciation is demonstrated by spending time alongside frontline employees rather than simply acknowledging their contributions.
Baldwin challenged attendees to consider how often they make themselves visible in the field. “How often are you at your bus depot? How often do you ride a bus?” he asked.
He said regularly riding routes and visiting bus depots allows transportation leaders to better understand the daily challenges drivers face while building trust throughout the department.
“How often do you just show up at a bus depot and get on a bus with a random driver and ride their route?” Baldwin said. “Do you know if you do that, how much clout you will gain? … They’ll see you not so much as a person that sits behind a desk, but rather than a person who understands what they go through.”
Baldwin added that leaders should focus on coaching employees rather than viewing every interaction as a disciplinary conversation, emphasizing the importance of treating staff members with respect while helping them improve.
Strategic Leadership and AI
Baldwin also emphasized the importance of establishing clear expectations throughout an organization.
He encouraged transportation departments to develop strategic plans, mission statements and operational goals that remain visible throughout the year rather than becoming documents that are referenced only during evaluations.
“You’ve got to have your mission, your vision and objectives,” Baldwin said. “People need to know what you’re about when they walk through the door.”
He said those expectations should become part of a department’s daily culture, giving employees a shared understanding of the organization’s priorities and creating accountability among coworkers rather than relying solely on supervisors.
For districts looking to improve efficiency, Baldwin encouraged transportation leaders to embrace artificial intelligence instead of avoiding it.
He said AI has become a valuable tool for drafting communications, analyzing transportation data, updating standard operating procedures, and identifying employee retention strategies.
“We’ve learned to embrace it,” Baldwin said. “Don’t shy away from it. Take it and use it to your advantage.”
In his department, AI has significantly reduced the time required to analyze operational data, allowing staff to produce reports for school board members and district leaders much more quickly than before.
Baldwin said the technology has also helped his team draft standard operating procedures, update employee handbooks and identify workforce trends that can guide recruitment and retention efforts. While AI can improve efficiency, he encouraged attendees to verify the information it produces before incorporating it into operational decisions.
As the session concluded, Baldwin encouraged attendees to continue learning from one another and strengthening the relationships they build across the profession, noting that collaboration is one of the industry’s greatest assets.
He reminded transportation professionals that the work they do carries tremendous responsibility and encouraged them to recognize the value of their contributions while supporting one another.
RENO, Nev. — A total of just over 1,010 years of student transportation experience sat in the “So, You Want to Become a Transportation Supervisor,” four-and-half-hour session July 11 during STN EXPO West.
Not only transportation experience but education experience as well, consultant Alexandra Robinson said, adding that everyone in the room is an educator. Also, among the presenters were industry veterans Timothy Purvis of Pupil Transportation Information, consultant Pamela McDonald, and Rosalyn Vann-Jackson, executive director of enrollment and student services at Broken Arrow Public Schools in Oklahoma.
Vann-Jackson started the first quarter of the seminar by explaining because the school bus serves as an extension of the classroom, employees have opportunities to positively influence students, colleagues and communities. As individuals advance into supervisory roles, however, their responsibilities and challenges often increase, particularly when managing adults, building trust and navigating organizational change, she said.
A central theme of her portion was “level setting,” or creating a shared understanding of expectations, priorities, values and workplace standards. Effective supervisors should establish common language, clearly communicate what employees can expect from leadership and connect operational decisions to the department’s central purpose: safely transporting students.
Rosalyn Vann-Jackson, executive director of enrollment and student services at Broken Arrow Public Schools in Oklahoma, speaking to STN EXPO West attendees.
Healthy Leadership
Vann-Jackson stressed that successful leaders listen before attempting to solve problems. By learning why employees stay, what motivates them and what challenges they face, leaders can develop more effective recruitment, retention and workplace improvement strategies. She shared how employee feedback helped her district target retirees who enjoyed working with children, contributing to significant staffing improvements.
Trust was described as the foundation of a healthy workplace culture. Supervisors build trust gradually by keeping promises, admitting mistakes, listening, giving employees credit, remaining consistent, and working alongside their teams. Trust can be quickly lost through favoritism, poor communication, broken commitments or unexpected demands.
The presenters also encouraged attendees to build relationships beyond their departments, including with unions, district administrators, school leaders and financial officers. Strong internal and external partnerships help transportation leaders advocate for employees, secure resources and create a culture that continues to succeed even when the supervisor is not present.
Building Culture
McDonald continued, discussing the importance of creating relationships. The retired director of transportation for Orange Unified School District in Southern California, noted that leaders should remain visible and available to employees rather than managing exclusively from an office. Regular briefings, informal conversations and opportunities for staff input can improve communication and reduce burnout. Employees should also be included in decisions that directly affect their work, such as selecting new buses, equipment or technology.
She emphasized that transportation departments benefit from the varied backgrounds, languages and experiences of their employees. Recognizing those strengths can improve service across an entire school district.
Successful transportation leaders must also build relationships with students, parents, teachers, principals, special education staff, district administrators, neighboring districts, contractors and community members. These partnerships can provide critical support during staffing shortages, operational changes and emergencies, McDonald said.
Departments should actively promote their accomplishments through awards, employee recognition, team events, professional development and public outreach. Positive visibility can strengthen employee pride, improve morale and demonstrate transportation’s value when district leaders consider budgets. Above all, employees should understand that their work reflects the department and supports the safe transportation of students.
Kristy Flick, operations supervisor for Poway Unified School District in California.
Kristy Flick, operations supervisor for Poway Unified School District in California, said in 1991 her first child was born and she was looking for work that was part-time, allowing her to choose her schedule. She became a sub driver for Poway for two years before becoming a permanent driver and then continued to move up the ranks – from training, to dispatching to routing for students with special needs.
“Then eventually a supervisory job came open, and I thought, oh, why not? I’ll just go for it and try it, and here I am,” she said, adding that the supervisor class gave her suggestions on how to boost morale.
She noted that after COVID-19, bringing camaraderie back to the department has been a challenge. “So that’s something that I want to take back and hopefully go forward with what I learned from here to help with our morale in Poway,” she said, adding it’s all about listening and being a positive person.
Data-Driven Decisions
Purvis continued, addressing data driven decisions. The retired director of transportation for Poway Unified and founder of PTI said transportation supervisors can use data to make stronger operational and budget decisions. Leaders do not need to be experts in spreadsheets or statistics, but they should understand how measurable information can confirm—or challenge—the assumptions made about their departments.
He distinguished between observations and key performance indicators. Statements such as “that bus is always late” or “drivers struggle with backing” may identify a concern, but they do not provide enough information to guide a decision. A key performance indicator uses a measurable number to show whether performance is improving, declining or remaining consistent.
Transportation departments already generate valuable data through routing systems, maintenance records, safety inspections, accident reports, training programs and employee attendance. However, that information is often kept in separate operational silos. Supervisors should connect data across departments to better understand the causes of delays, vehicle problems, accidents, staffing challenges and inefficient routes.
Useful measures may include on-time performance, preventable accidents, driver absenteeism, fleet availability, cost per mile, student ride times, bus capacity and the number of students transported, Purvis explained. These figures become especially important when district administration request budget reductions without reducing service.
He encouraged supervisors to begin with one operational area, select a meaningful measurement and review it consistently. Data should support practical decisions, not be collected simply for the sake of creating reports.
Ian Moter, assistant transportation director for Converse County School District #2 in Wyoming.
Ian Moter, assistant transportation director for Converse County School District #2 in Wyoming, noted Purvis’ section was of particular interest to him. Moter lost his full-time job and started driving a school bus because he had a CDL. He drove a bus for one full school year, and when he returned several staff members quit for personal reasons, and his superintendent provided him to step in to help in the interim. Since then, he was hired to be the assistant director, a move he described as stressful.
“Mostly just because of learning the business side of things,” he said. “I find that 90 percent of these issues, doesn’t come from bus driving specifically. It’s more so learning people and process, and I’m a big proponent of people over process.”
He added the district has implemented Tyler Technologies and Geotab, which have been instrumental in their program. “Just optimizing, finding the data that we need to find our inefficiencies with just maintenance as well as routing and safe student pickup,” he said, adding that they’ve been able to reduce routes from seven to four. “… All of our office staff is brand new to the office staff side of things. My dispatcher is a retired bus driver. She worked for our district for 24 years on one single dedicated route, and so none of us had any of the office experience. And Tyler Tech has helped us be able to just move straight through seamlessly.”
He said he resonated with the section on KPIs. “I really took a lot from this last session about KPIs, and rather than trying to find a people source of ongoing issues, trying to see if there’s an overarching problem that could be used across the board to help efficiencies.”
Alexandra Robinson speaking at the So You Want to Become a Transportation Supervisor class at STN EXPO 2026.
Being a Good Leader
Robinson concluded the seminar with information on how to lead in not only good times but bad. She explored how workplace culture, accountability and self-awareness affect transportation departments. Employees should feel motivated, respected and comfortable communicating with supervisors, said the veteran transportation professional who had stints as director of San Diego Unified in California and as executive director for the New York City Department of Education.
In unhealthy organizations, even a request to meet with a manager can create anxiety, physical stress and fear. Leaders must recognize warning signs such as bullying, passive-aggressive behavior, apathy, poor follow-through and persistent negativity before they spread throughout the department.
Robinson noted that supervisors cannot continually excuse harmful behavior because of staffing shortages, seniority or a lack of documentation. Allowing unsafe or disruptive employees to remain without accountability damages trust and signals that standards are optional. Leaders should ask whether they would confidently allow an employee to transport their own child, said the former National Association for Pupil Transportation president, adding that any hesitation should prompt immediate action. Staffing gaps should not be managed by routinely pulling dispatchers, mechanics, supervisors or directors away from essential responsibilities, as these short-term solutions can create larger safety and liability risks.
Supervisors should also evaluate whether employees are serving in roles that match their skills, Robinson said. Some individuals excel at managing systems, technology or routing but may not be suited in leading people. Cross-training, reassignment and thoughtful organizational planning can help employees contribute successfully without forcing everyone onto the same career path.
Robinson’s section also addressed professional growth. Hard work alone is not enough if results are invisible, and loyalty should not keep employees in unhealthy environments. Leaders should seek meaningful feedback, avoid treating burnout as an accomplishment and focus on progress rather than perfection. Networking and stepping outside one’s comfort zone she described as essential to advancement.
When hiring future leaders, supervisors should look beyond technical experience and consider enthusiasm, curiosity, honesty and willingness to learn, she said. Strong leadership potential often appears in candidates who care deeply about the work, understand their limitations and demonstrate a genuine desire to improve student transportation, Robinson concluded.
RENO, Nev. – In an anecdote-filled leadership training, branding expert Bruce Turkel leveraged his 30-plus years of business and marketing experience to advise transportation directors on becoming more customer-focused.
Seeing Through Their Eyes
The cornerstone of Turkel’s presentation to a room full of transportation directors and vendor partners on day two of the TD Summit during STN EXPO West was to “figure out the difference between what you sell and what you exchange for money.” There is a deeper meaning to the former, he noted.
A Domino’s Pizza executive once admitted, “I’m not in the pizza business, I’m in the problem business.” People don’t buy the product because it’s their favorite food but because it’s a convenient solution for a quick dinner or birthday party to avoid a spouse’s annoyance or a child’s tears, Turkel pointed out.
The “All About Them” author added that the pupil transportation industry already correctly centers around people and specifically kids, rather than details like bus features or superlative tires.
“What you sell is treating every child like your own,” he stated. “What you sell is peace of mind.”
This, he said, holds true even as technology like autonomous buses and AI routing permeate the industry. “All these things will affect what you exchange for money – none of them will affect what you sell,” Turkel declared. “You don’t buy your own products. You don’t use your own services,” he continued. “Perhaps there’s something your audience or your clients see that you don’t.”
Turkel related how he helped a top Bacardi executive see that the company needed a particular marketing strategy to sell high-end liquor to younger generations accustomed to cheaper options. He also shared how he had to see things from his wife’s perspective as a healthcare professional when purchasing a car safe enough for their kids, which led him to swap his convertible for a safety-focused Volvo.
Student transporters, he noted, must consider the perspectives of parents, school boards, superintendents, financial analysts, legislators, mayors and more.
Like Uber and Lyft overtook taxis and AirBnB supplanted hotels, he said, a quality service will supersede an apathetic one. Similar to market research conducted by large brands, he suggested asking parents for their input and sincerely listening since “clients and customers care about how they feel.”
“What you sell is peace of mind.”
– Bruce Turkel
Communicating With Clarity
Turkel advised being clear and not clever, since even the catchiest or sincerest messaging can fail if its audience doesn’t connect with it.
Tracing Nike’s journey from a running shoe company to a ubiquitous brand, he explained how the “Just Do It” slogan came about in the late 1980’s to circumvent buyers’ exercise excuses by selling empowerment and potential. Student transporters must similarly reframe to understand that they empower the economy by providing access to education, he said.
“You’re not moving buses, you’re not moving children, you’re moving opportunity,” Turkel stated.
Parents have a lot of emotion tied up with anything relating to their children, he noted. Thus, student transporters may be able to rework or repackage their offerings without introducing anything new or “repainting the bus.”
“Hearts, then minds,” he advised. “Make an emotional connection before an intellectual connection.”
From watches to coffee to cars, some things become more than just products, Turkel explained. Fancy watches showcase wealth and legacy, whereas Starbucks stores became a third space for community, and vehicle brands came to have associations: Toyotas with reliability, Mercedes-Benz with success, Jeeps with ruggedness, Audi with design and more.
For millions of families across the U.S., the yellow school bus is the face of the school system and even the city, since the driver is often the first face they see in the morning. This is a powerful reflection for transportation managers and an effective way to motivate staff to do their jobs well, Turkel suggested.
Noting how an STN EXPO attendee mentioned that it’s important to avoid reassigning bus drivers, he confirmed that his childhood driver, Ms. Williams, was indeed valued by parents who would inquire after her if she was absent.
“Make an emotional connection before an intellectual connection.”
Managing expectations helps retain trust even if problems arise, Turkel explained. When Discovery Channel expanded into the Latin American market, an executive realistically aimed to be “everyone’s second-favorite channel” by carrying low pressure but universal programming.
Billing a student transportation operation as the best, fastest, cheapest, or anything similar is a mistake since “the -est always comes back to bite you,” he said.
He also emphasized the importance of media training for transportation employees. He shared a stunt involving surprise cameras and a fake emergency which revealed the Guatemalan government didn’t know how to handle PR crises and ultimately led to a positive revamp of its tourism messaging.
And internal consistency is so important, Turkel said his company reviewed its core tenants and fire-able offenses every week.
“Any way you look at it, you can use your authentic truth to manage expectations,” Turkel said. Many problems student transporters face – cutting costs, time management, limited help and more – besiege parents too, he explained, creating another connection point between the two.
While parents prioritize safe yet prompt busing, regulators care about compliance and financial managers highlight cutting costs, Turkel advised transportation directors to take a 50,000-foot view of things. By “creating universal stories,” much like Disney theme parks build on nostalgia to create loyal customers, everyone can become aligned in the mission, he added.
“Reliability creates trust and trust creates value,” Turkel said, adding that value overcomes competition, objections and complications.
“Any way you look at it, you can use your authentic truth to manage expectations.”
– Bruce Turkel
Leading Change with Purpose
“Change is a continual wave of moving parts that are happening all the time,” Turkel declared. Even AI isn’t the cataclysmic new thing it’s feared to be, he said. The internet, radios, movies, the printing press and other innovations were all considered radical at first, then ultimately recognized as beneficial.
“It’s your job to look at things a different way,” Turkel affirmed. He cautioned that leaders especially must understand the intersection of what the company wants and what customers want, then leverage storytelling to guide everyone toward the goal.
“People don’t follow instructions or leaders, they follow stories,” he added.
“We don’t just bring our training, we bring our hearts,” commented LaTedra Bailey, director of transportation for Huffman Independent School District in Texas.
“That’s your story right there,” Turkel told the room of student transporters.
“We don’t just bring our training, we bring our hearts.”
– LaTedra Bailey, Director of Transportation, Huffman Independent School District (Texas)
Survey Stats
Prior to the start of the TD Summit, the transportation director participants took a survey indicating their fleet makeups, procurement projections and areas of focus.
Almost three-quarters of districts represented run their own pupil transportation, while the rest involve contractors in some fashion. Just over 60 percent of operations transport 5,000 or fewer students. Gasoline and diesel overwhelmingly make up their top energy choices, with 40 percent choosing electric. Over half of respondents applied for federal or state funding for clean fuel buses.
Non-yellow bus options came in strong, with 75 percent utilizing vans in their operations, followed by Type A buses at 67 percent, then SUVs and sedans at 63 percent. Type C and D buses came in at about 60 percent each.
About 40 percent plan to spend $100,000 to $500,000 on new buses over the next year, while almost 18 percent plan to spend $1 million to $3 million. The highest concentration, 33 percent, indicated they look to spend $1,000 to $50,000 on new equipment or technology. Almost 40 percent allotted $50,000 to $250,000.
Their top three challenges indicated by directors are: Driver retention and shortages, student behavior and bullying incidents, and improved driver safety and performance. The number one product category that interested them is Artificial Intelligence and Predicative Analytics.
Student transportation professionals looking to advance to the next leadership level are encouraged to sign up for the “So You Want to Be a Transportation Supervisor” professional development special training at STN EXPO West.
This annual conference seminar allows student transporters to prepare for a transition to a supervisor role or re-evaluate their leadership skill sets. Led by a panel of seasoned instructors and industry experts, this seminar is ideal for those looking to improve their operations, department culture and staff interactions. It will be held on Saturday, July 11 as an all-day training from 11:30-5 p.m.
The instructor team is led by Alexandra Robinson, a former executive director of transportation and current industry consultant and expert witness as well as TSD Conference tenured faculty member. She is joined by Tim Purvis of consultant group Pupil Transportation Information; and Rosalyn Vann-Jackson, chief support services officer for Broken Arrow Public Schools in Oklahoma and Pam McDonald, a retired director of transportation and current consultant.
What the Professional Development Consists Of
For those who are newer to the industry, the instructors will discuss making data driven leadership decisions, understanding return on investment, and collaborating with the right people at the district to move transportation operations forward. They will also speak on team building, customer service, communication strategies, workplace culture and productivity as well as operational considerations such as employee retention, principles of proper routing and managing data.
Attendees will be exposed to interactive leadership and team-building scenarios. The instructors through how to approach them with a correct human resources perspective. Attendees will also have a chance to ask questions of the instructors and gain invaluable supervisor and leadership lessons from real-life experiences.
At the end of the professional development class, attendees will have received strategic and practical advice that will better equip them to lead in hard times and build strong relationships with their team.
Electric school bus manufacturer RIDE will sponsor refreshments during the session. There is a maximum of 100 participants. Separate registration is required at no additional charge.
STN EXPO West will be held July 9-15 at the Peppermill Resort in Reno, Nevada. Attendees will have access to a week of educational sessions based on the challenges facing the industry, training classes to improve operations, networking events to bring peers together for problem-solving and innovative experiences such as the Ride and Drive/Live Product Demo, the STN EXPO Trade Show and the Transportation Director Summit. Register at stnexpo.com/west.
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