Senior Technical Project Manager - SaaS

Location: Reading, PA, United States

Why Join Digital Products at Penske
Most people know Penske for our big yellow trucks. But we’re so much more than that. At Penske we have a 50-plus year history of leading the transportation and supply-chain industry, delivering world-class and award-winning technology solutions.

What most people don’t know, we are just as much a data company as we are a transportation and supply chain company. We collect and analyze billions of datapoints each year, through over 300+ advanced analytical models and integrate insights from our fleet, maintenance operations, and logistics networks to give customers a more complete view of their supply chains. That connected intelligence allows us to anticipate issues, optimize resources, and deliver reliable outcomes across transportation and logistics for our customers. Penske continues to invest in, and grow, our digital products – and we need talent at all levels to help us advance and continue to lead our industry.

While data is very important, the key to our success is our people. You’ll work alongside great people and on really cool projects. Ultimately, you’ll help develop and ensure our technology solutions keep our company and our customers moving forward.

Position Summary: 
The Senior Technical Project Manager is a senior-level, cross-functional leader within Penske's Digital Fleet Management group, responsible for driving the successful delivery of the company's most complex and strategically significant IT initiatives. This role bridges the gap between technical execution and business strategy — translating ambiguous, large-scale engineering challenges into clear, phased roadmaps that deliver measurable outcomes on time and within budget.

By combining deep technical literacy with advanced stakeholder leadership, the Senior Technical Project Manager serves as the connective tissue across engineering, product, design, and business teams — ensuring that cross-functional initiatives are delivered predictably, efficiently, and in alignment with Penske's strategic priorities. This includes ownership of program budgets, resource planning, vendor and SaaS relationship management, and compliance coordination across a high-complexity, fast-moving technology environment.

As a Senior Technical Project Manager at Penske, you will manage multiple high-priority IT programs simultaneously, acting as both a strategic advisor to leadership and a hands-on execution partner to engineering teams — shielding developers from organizational friction while driving accountability across every stakeholder involved in delivery.

This position is based at Penske Corporate Offices in Reading, PA. This is an office first position, in office four days a week.

Major Responsibilities: 

Project Planning & Roadmap Development 
• Lead discovery, framing, and requirements gathering to develop business cases, project charters, and structured execution roadmaps for complex technical initiatives.
• Build and maintain work breakdown structures, milestone schedules, and baseline delivery timelines with clearly defined dependencies and critical path deliverables.
• Work directly with IT and business process owners to define project scope, deliverables, and resource requirements aligned to strategic objectives.
• Act as project architect to ensure all cross-functional solution components are sequenced and integrated effectively.

Cross-Functional Alignment & Stakeholder Management 
• Serve as the central coordination point across engineering, product, design, operations, and business stakeholders to ensure unified communication and shared accountability.
• Facilitate project working sessions, steering committee report-outs, and executive status updates — communicating scope changes, risks, and issues with clarity and appropriate urgency.
• Manage stakeholder expectations through tactful negotiation, proactive communication, and independent prioritization across multiple concurrent initiatives.
• Translate complex technical requirements into actionable user stories or specifications accessible to both technical and non-technical audiences.

Project Execution & Delivery Management 
• Own full project lifecycle execution across waterfall and agile frameworks, including sprint ceremonies, daily stand-ups, product demos, and retrospectives.
• Monitor all program activity, budget, and resources to ensure initiatives remain on schedule, within scope, and within budget with no rework required.
• Hold all project resources accountable to agreed-upon deliverables, following through on all action items and issues through to resolution.
• Effectively close projects upon final deployment, including post-deployment support and formal project completion documentation.

Risk, Dependency & Scope Management 
• Proactively identify, assess, and monitor project risks, scope creep, and technical dependencies before they impact delivery timelines.
• Maintain a structured risk register and communicate mitigation strategies and escalation paths to leadership in a timely manner.
• Map and manage tightly coupled cross-team dependencies to ensure deliverables land in the correct sequence without creating development bottlenecks.
• Coordinate end-to-end compliance processes, including SOC 2 Type II and PCI certifications, ensuring timely completion of audit-readiness activities across technical teams.

Budget & Resource Management
• Develop and manage project budgets that capture all expenditures across the full project lifecycle, including CapEx vs. OpEx tracking and forecasting.
• Efficiently plan and prioritize resources based on deliverable dates, project scope, and strategic goals.
• Lead vendor sourcing activities including development of RFPs, RFQs, and RFIs, and validate SOW deliverables through active vendor management.
• Manage high-value SaaS vendor relationships across the full lifecycle — including vendor shortlisting, contract negotiations, and subscription renewals — to optimize cost and service delivery.

Engineering Enablement & Process Optimization 
• Shield development teams from organizational noise by managing stakeholder pressure, timeline complexity, and dependency resolution so engineers can maintain delivery focus.
• Continuously evaluate and improve Agile and SDLC processes to reduce friction, increase developer velocity, and minimize cycle time from commit to deploy.
• Identify and implement lean process improvement opportunities and approved project management methodologies and tooling.
• Actively track and unblock cross-functional technical integrations across the organization, resolving coordination gaps between engineering squads, APIs, and dependent systems.

Governance, Reporting & Continuous Improvement 
• Maintain adherence to the Penske Project Management Methodology, ensuring all documentation, tools, and reporting standards are consistently applied across assigned projects.
• Produce and distribute ongoing project status reports, portfolio KPI dashboards, and project measurement outputs to internal and external stakeholders.
• Conduct after-action reviews upon project completion to capture lessons learned and identify process improvement opportunities.

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