Director of Software Engineering

Job Description

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

We are seeking a Director of Software Engineering to provide strategic leadership across multiple engineering teams responsible for delivering mission-critical systems that power our platform. As a senior leader, you will define the technical vision, drive organizational excellence, and ensure alignment between engineering capabilities and business strategy. You will partner closely with executive leadership and cross-functional teams to shape the future of our platform. This role is ideal for a leader who thrives in scaling engineering organizations while delivering high-impact, high-quality solutions.

Essential Responsibilities

Strategic Leadership and Vision

• Define and execute the engineering vision and roadmap in alignment with company objectives and market opportunities.
• Partner with executive leadership to shape technology strategy, investment priorities, and long-term platform evolution.
• Drive innovation initiatives and evaluate emerging technologies to maintain a competitive advantage.
• Establish engineering KPIs and metrics to measure team effectiveness, delivery quality, and operational excellence.
• Lead offshore and nearshore remote teams effectively, including hybrid teams comprised of employees and contractors.

Organizational Leadership and Talent Development

• Lead, mentor, and develop multiple engineering managers and their teams, fostering a culture of accountability, collaboration, and continuous improvement.
• Build and scale engineering teams through strategic hiring, retention strategies, and succession planning.
• Create career development frameworks and growth opportunities to attract and retain top engineering talent.

Technical Excellence and Architecture

• Provide architectural oversight and technical governance across all engineering initiatives, ensuring scalability, security, and reliability.
• Drive adoption of modern engineering practices, including cloud-native architectures, microservices, and DevOps methodologies.
• Establish and enforce coding standards, design principles, and security policies across the engineering organization.
• Oversee technical debt management and platform modernization efforts.
• Enable high-traffic, high-transaction architectures.

Delivery and Operational Excellence

• Own engineering delivery across multiple product lines, ensuring projects are delivered on time, within budget, and to quality standards.
• Manage engineering budgets, resource allocation, and vendor relationships.
• Drive operational excellence through robust monitoring, incident management, and continuous improvement processes.
• Ensure compliance with enterprise security, regulatory requirements, and industry best practices.

Cross-Functional Collaboration

• Serve as an engineering representative in executive discussions, board presentations, and strategic planning sessions.
• Partner with Product, Operations, and Business Development to align engineering priorities with market demands and customer needs.
• Communicate technology vision, risks, and tradeoffs effectively to both technical and non-technical stakeholders.
• Build strong relationships with external partners, vendors, and technology communities.

Requirements

Qualifications

Education and Experience

• Bachelor’s degree in Computer Science, Software Engineering, or equivalent experience.
• 15+ years of software engineering experience, with at least 8+ years in engineering leadership roles managing managers.
• Proven track record of building and scaling engineering teams in high-growth, fast-paced environments.

Technical Expertise

• Deep expertise in software architecture, system design, and modern development practices.
• Strong background in cloud platforms (Azure, AWS, or GCP), distributed systems, and API-driven architectures.
• Experience with enterprise systems integration, high-transaction platforms, and big data technologies.
• Familiarity with DevOps practices, CI/CD pipelines, and infrastructure automation.
• Knowledge of middleware, message brokers (Kafka, RabbitMQ), and event-driven architectures.

Leadership Competencies

• Demonstrated ability to inspire, develop, and retain high-performing engineering teams.
• Executive presence with excellent communication and presentation skills.
• Strategic thinking with the ability to translate business objectives into technical roadmaps.
• Experience managing engineering budgets and resource planning.
• Strong problem-solving skills with a results-oriented mindset.
• Ability to lead remote nearshore and offshore teams.

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.