Director of Tolling Operations at PrePass

About PrePass

PrePass is North America's most trusted weigh station bypass and toll management platform. We’re transforming how the transportation industry operates—creating solutions that keep trucks moving safely, efficiently, and compliantly. This means making bold decisions and building systems that support not only fleets but the broader economy. It all starts with enabling commercial vehicles to keep rolling with seamless toll management, weigh station bypass, and safety solutions. It’s what we do best, and we do it to meet the demands of the road every day.

That’s why people join us: our solutions are implemented in real-time, on highways and interstates across the nation, helping fleets go farther, faster. This work challenges and rewards, presenting complex problems that need ambitious answers. We hire bold thinkers with a heart for impact, a passion for progress, and the optimism to shape the future of transportation.

About the Role

The Director of Tolling Operations is responsible for leading the people, processes, systems, and controls that support PrePass tolling services. This leader will build and maintain a highly disciplined operating environment that delivers accurate, timely, and consistent results for customers and tolling partners.

This role requires a hands-on people leader who sets clear expectations, creates accountability, develops strong teams, and continuously improves how work gets done. The Director will also lead efforts to automate and optimize tolling processes, reduce manual work, improve accuracy, strengthen operational controls, and support the continued growth of the tolling business.

Responsibilities

Operational Excellence & Execution

• Lead day-to-day Toll Operations, focusing on accuracy, efficiency, quality, and customer outcomes.

• Create and maintain a highly disciplined operating environment with clear processes, controls, service levels, and performance standards.

• Develop operational KPIs to measure productivity, quality, turnaround times, exception rates, and team performance.

• Establish operational rhythms including leadership reviews, daily huddles, performance reviews, and escalation processes.

• Ensure operational readiness for growth while maintaining service quality and financial performance.

• Drive root-cause analysis and corrective actions to eliminate recurring operational issues.

Process Optimization & Automation

• Identify opportunities to eliminate manual work, streamline workflows, and improve operational scalability.

• Partner with Product, Technology, Data, and Business Systems teams to automate tolling processes and back-office workflows.

• Lead continuous improvement initiatives that improve throughput, reduce cost-to-serve, and enhance accuracy.

• Champion the adoption of new technologies, AI capabilities, and automation tools that improve operational efficiency.

• Establish a culture focused on measuring, improving, and optimizing every critical operational process.

People Leadership

• Build, develop, and retain a high-performing Toll Operations team.

• Coach and mentor managers, supervisors, and individual contributors.

• Create a culture of accountability, ownership, collaboration, and continuous learning.

• Establish clear roles, responsibilities, and performance expectations across the organization.

• Develop succession plans and career development opportunities for team members.

• Foster strong cross-functional relationships and break down operational silos.

Analytics & Business Performance

• Use data to drive operational decisions, prioritization, and resource planning.

• Monitor operational trends and proactively identify improvement opportunities.

• Establish meaningful performance metrics and reporting that provide visibility to leadership.

• Build forecasting and capacity planning models to support business growth.

• Deliver regular operational reviews with actionable insights and recommendations.

Cross-Functional Leadership

• Partner closely with Product, Technology, Finance, Customer Success, Customer Care, and Compliance teams.

• Drive alignment across departments to improve customer experience and operational outcomes.

• Act as the operational voice for tolling initiatives, new capabilities, and process improvements.

• Support strategic projects, system implementations, and business transformation efforts.

Requirements

Qualifications

• Bachelor’s degree in business, operations, finance, technology, or a related field, or equivalent professional experience.

• Ten or more years of progressive operations experience, including at least five years leading managers or operational teams.

• Demonstrated success leading complex, transaction-based, financial, payments, transportation, or similarly regulated operations.

• Proven ability to create structure, accountability, and operational discipline in a growing or changing environment.

• Experience leading process improvement, workflow automation, system implementation, or digital transformation initiatives.

• Strong understanding of operational controls, reconciliations, risk management, service levels, and performance measurement.

• Demonstrated ability to develop people, build strong teams, and manage performance effectively.

• Strong analytical, problem-solving, and decision-making skills.

• Excellent communication and cross-functional leadership capabilities.

• Tolling, transportation, payments, fleet services, or financial transaction experience is strongly preferred.

Leadership Attributes

The successful candidate will be

• A disciplined operator who values accuracy, consistency, preparation, and follow-through.

• A visible and engaged people leader who develops employees and holds teams accountable.

• A systems thinker who can connect people, processes, technology, controls, and customer outcomes.

• A continuous-improvement leader who challenges inefficient or overly manual ways of working.

• Comfortable moving between strategic planning and detailed operational execution.

• Proactive in identifying risks and decisive in resolving issues.

• Collaborative, direct, and transparent in communicating with employees, partners, and senior leaders.

• Customer-focused, with a clear understanding that strong operations are foundational to customer trust.

Measures of Success

Success in this role will be measured through:

• Transaction accuracy and processing timeliness.

• Reconciliation accuracy and resolution of outstanding exceptions.

• Reduction in violations, preventable fees, errors, and customer-impacting issues.

• Achievement of service-level commitments.

• Backlog volume and aging.

• Team productivity, engagement, retention, and development.

• Reduction in manual processing and measurable automation benefits.

• Strength and consistency of operational controls.

• Customer satisfaction and resolution times.

• Ability to scale tolling operations efficiently as the business grows.

Ideal Profile: A leader who combines operational discipline with strong people leadership; someone who can build a culture of accountability while modernizing tolling operations through technology, automation, analytics, and continuous process improvement.

Benefits

How We Will Take Care of You

• Robust benefit package that includes medical, dental, and vision that start on date of hire.
• Paid Time Off, to include vacation, sick, holidays, and floating holidays.
• Paid parental leave.
• 401(k) plan with employer match.
• Company-funded “lifestyle account” upon date of hire for you to apply toward your physical and mental well-being (i.e., ski passes, retreats, gym memberships).
• Tuition Reimbursement Program.
• Voluntary benefits, to include, but not limited to Legal and Pet Discounts.
• Employee Assistance Program (available at no cost to you).
• Company-sponsored and funded “Culture Team” that focuses on the Physical, Mental, and Professional well-being of employees.
• Community Give-Back initiatives.
• Culture that focuses on employee development initiatives.
• Company-wide bonus and commission plans.

Join Us

At PrePass, our mission drives us.

We invest in relationships. We challenge ourselves to innovate and improve. We win together. Simply put, we live our Core Values.

Ready to help move the transportation industry forward? Join us and let’s drive progress—together.