Welcome to The Right Ride, a video interview series from EverDriven that highlights leaders navigating the most complex challenges in student transportation. Across the series, we speak with transportation professionals who understand that getting students to school is more than an operational task. It is a daily promise to families.
In this episode, we sat down with Greg Jackson, the new General Manager of Routing Services at EverDriven. Greg brings more than 20 years of experience working alongside school districts, leading transportation teams through budget constraints, enrollment shifts, and rising student needs.
His perspective makes one thing clear. Transportation reliability builds trust. And modern routing determines whether that trust holds.
A Visible Promise to Families
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After two decades on the district side, Greg has seen what stays the same and what evolves.
Transportation, he explains, remains one of the most visible commitments a district makes. When buses arrive on time, families feel confident. When service breaks down, trust erodes quickly. Few departments sit so publicly at the center of community perception.
What has changed is the complexity.
Student needs are more individualized. Specialized transportation requests continue to grow. Enrollment trends in many districts are declining. Budgets tighten as revenue follows those enrollment shifts. At the same time, daily route coverage remains non-negotiable.
Transportation teams operate under constant pressure. Not because commitment is lacking. Because variables multiply. That rising complexity demands a more modern approach to routing.
Why Partnership Matters
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Greg’s move to EverDriven stemmed from a pattern he kept seeing across communities.
Districts were working tirelessly. Yet many attempted to solve structural challenges in isolation. Routing teams were cutting, pasting, rebuilding, and reacting in real time. Leaders were scrambling to fill vacancies while also redesigning routes to compensate.
The work was heroic, but it was unsustainable.
At EverDriven, Greg saw the opportunity to scale what he learned on the district side. Not to replace district expertise, but to strengthen it.
The goal is collaboration. District leaders bring deep community knowledge. Routing specialists bring time, technical depth, and continuous oversight. Together, they can build systems and rely on technology to reduce daily pressure and stretch limited budgets further.
Reliability improves when teams share the load with trusted partners like EverDriven.
Modern Routing is Continuous
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Greg defines modern routing as a continuous improvement process.
Historically, many districts treated routing as an annual exercise. Routes were set before school started. Adjustments followed as issues emerged. Departments supporting students with disabilities, McKinney-Vento offices, and specialized programs often introduced changes midstream.
Routing teams reacted. Modern routing flips that pattern. It requires regular collaboration between routers, district leadership, and administrators. It anticipates change rather than absorbing disruption after the fact.
Routes are reviewed consistently. Efficiencies are identified together. The focus remains operational sustainability. The objective is not service reduction. It is building routes districts can realistically operate every single day.
Reducing the Daily Routing Scramble
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Greg describes what many district leaders recognize immediately. The scramble.
Vacancies appear. Mechanics, dispatchers, supervisors, and directors step into operational gaps. Forecasted attendance collides with staffing shortages. Routes are adjusted under pressure. Every adjustment consumes leadership bandwidth.
Dedicated routing support changes that equation. Specialists who understand routing software deeply can compress routes intelligently. They can analyze patterns across days, weeks, and months. They can provide steady oversight while district leaders focus on broader operational demands.
Reliable eyes on routing create breathing room. And breathing room allows leadership to think strategically rather than reactively.
From Budget Line to Access Investment
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Transportation often becomes a target during budget discussions. Leaders might propose cuts before they fully explore routing efficiencies. Districts question positions before analyzing route design.
Greg advocates for a different approach. He recalls presenting twice yearly to his district’s board, delivering what he called the “state of transportation.” Those updates provided data, route counts, student volumes, service demands, and operational challenges.
As a result, education replaced assumption.
Transportation leaders must advocate for their departments, and show how routing efficiencies can preserve service. They must frame transportation as an access investment tied directly to attendance, funding, and student opportunity.
When transportation is part of the strategic conversation, it stops being viewed solely as a cost center.
Defining the Next Era of Student Transportation
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The next era of school transportation will be defined by efficiency under financial pressure, Enrollment declines are unlikely to reverse quickly. Districts must operate sustainably within that reality.
That demands leaders who advocate. Leaders who collaborate across departments. Leaders who see themselves not as separate operators but as integral administrators shaping district success. Transportation leadership is evolving.
It requires operational precision, political awareness, strategic communication, and continuous routing improvement. Districts that embrace that mindset will navigate complexity with greater stability.
Key Takeaways
From EverDriven’s General Manager of Routing Services Greg Jackson’s experience, several principles stand out for transportation directors:
- Reliability builds trust with families.
- Complexity requires continuous routing, not annual resets.
- Collaboration reduces routing scrambles.
- Data-driven advocacy protects transportation services.
- Efficiency under financial pressure defines the future of transportation leadership.
Student transportation is a living system that must adapt daily. Modern routing is the discipline that keeps that system stable.
About the Series
The Right Ride shares perspectives from leaders shaping the future of student transportation. From operational design to strategic advocacy, the series explores how districts can build systems that protect access, reliability, and student stability.
To learn more about building a routing strategy designed for today’s realities, connect with EverDriven.
Courtney Pallotta is an energetic, customer-driven marketing executive with more than 20 years of experience leading go-to-market strategy, branding, product marketing, demand generation, and customer advocacy for startup and growth-stage companies. As CMO at EverDriven, she leads the GTM team in delivering modern, student-centered transportation solutions that meet every student’s unique needs.
Courtney has built and scaled marketing functions across some of the most dynamic enterprise technology categories, from data warehousing and analytics to cloud infrastructure, data privacy, and SaaS. She has taken companies from stealth through IPO, led acquisitions, launched open-source platforms, and consistently built marketing engines that drive pipeline and market position. Along the way, she has developed a deep belief that the best marketing is both simple and authentic, and that listening to customers is the foundation for great products and lasting communities.
Outside of EverDriven, Courtney serves as a Board Member at the Gilliam Center for Entrepreneurship, where she mentors the next generation of business leaders.
