Technical Program Manager
PrePass · Remote
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
As PrePass scales from a bypass-and-tolling provider into a unified compliance ecosystem, the complexity of delivering software has grown dramatically. Multiple product lines, a newly acquired codebase, state agency integrations, and partner marketplace commitments all compete for engineering capacity. We're looking for a Technical Program Manager to bring structure, predictability, and cross-team alignment to how we plan, execute, and ship.
This is a high-visibility role working at the intersection of engineering, product, and operations — someone who can translate roadmap ambitions into realistic delivery plans and hold the organization accountable to them.
Problems You'll Help Solve
Unpredictable Release Cadence
Teams building across bypass, tolling, compliance, and hardware-integrated systems operate on different rhythms. Create and maintain a structured release calendar to reduce surprises for customers, state agency partners, and internal stakeholders.
Engineering Capacity Visibility
Leadership needs to make portfolio-level tradeoffs (new integrations vs. platform stability vs. compliance features) but lacks a consistent view of what teams are working on and when it will land.
Cross-Team Dependency Management
A delay in any one integration/update/tool can block multiple teams. Dependencies need owners and visibility.
Essential Responsibilities
Program Planning & Delivery
- Own the integrated delivery roadmap across PrePass product lines: bypass, toll management, safety alerts, INFORM analytics, and compliance.
- Establish and maintain a dependable release schedule, coordinating across engineering, product, QA, and operations.
- Drive program kickoffs, milestone reviews, and retrospectives — creating accountability without unnecessary bureaucracy.
- Translate product roadmap priorities into phased, executable plans with clear owners, timelines, and risk mitigations.
Cross-Functional Coordination
- Map and track cross-team dependencies, escalating blockers before they become delays.
- Facilitate alignment between engineering teams.
Visibility & Reporting
- Build and maintain program dashboards that give engineering leadership and the CTO a real-time view of delivery health.
- Produce clear, concise executive status updates — surfacing risks, decisions needed, and milestone progress without noise.
- Define and track engineering KPIs: cycle time, release frequency, defect escape rate, and on-time delivery percentage.
Process Improvement
- Identify and eliminate recurring sources of delay — unclear requirements, late dependency discovery, incomplete acceptance criteria.
- Standardize Agile ceremony practices across teams to improve sprint predictability and retrospective follow-through.
- Lead post-incident reviews on missed releases, building a culture of blameless learning.
Requirements
Qualifications
- 5+ years of program or project management experience in a software product company.
- Demonstrated track record of improving release predictability across multiple engineering teams.
- Strong command of dependency mapping, risk management, and critical path analysis.
- Ability to communicate technical tradeoffs clearly to non-technical executives and external partners.
- Proficiency with Agile methodologies and tooling (Jira, Confluence, or equivalent).
Bonus Points For
- Background in transportation, logistics, fleet technology, or regulatory compliance software.
- Experience managing integrations with third-party telematics or marketplace platforms.
- Exposure to post-acquisition integration programs.
- Familiarity with .NET / Azure cloud environments (enough to understand engineering discussions, not to code).
What Success Looks Like in 90 Days
- Published and socialized an integrated program calendar covering all active product lines through end of year.
- Identified the top 3 recurring sources of delivery delay and proposed mitigation plans.
- Established a weekly program health report used by the CTO and product leadership.
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.
- 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.
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.