[Hiring] Technical Program Manager @PrePass

Role Description

As PrePass scales from a bypass-and-tolling provider into a unified compliance ecosystem, the complexity of delivering software has grown dramatically. 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: Create and maintain a structured release calendar to reduce surprises for customers, state agency partners, and internal stakeholders.
• Engineering Capacity Visibility: Provide leadership with a consistent view of what teams are working on and when it will land.
• Cross-Team Dependency Management: Ensure dependencies have owners and visibility to prevent delays.

Essential Responsibilities

• 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.
• Map and track cross-team dependencies, escalating blockers before they become delays.
• Facilitate alignment between engineering teams.
• 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.
• 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.

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

• 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.