Senior Technical Project Manager - SaaS

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.

Qualifications

Qualifications:

• Bachelor's degree in Computer Science, Information Systems, Management Information Systems, or Business Administration required; equivalent work experience will be considered.
• Minimum 6 years of proven technical project management experience in a complex, cross-functional IT environment required.
• Minimum 4 years of hands-on experience in an IT engineering function (e.g., software development, QA, systems architecture, or infrastructure) required.
• Project Management Professional (PMP) certification or formal project management training required; Agile/Scrum certifications (e.g., CSM, SAFe) preferred.
• Advanced proficiency in Agile, Scrum, Kanban, and Waterfall project management methodologies required.
• Demonstrated experience with project management and collaboration tooling including Jira, Confluence, or Linear required.
• Proven ability to manage full project lifecycle — initiating, planning, executing, controlling, and closing — for large-scale, high-complexity IT initiatives simultaneously.
• Strong financial acumen including experience managing project budgets, CapEx vs. OpEx forecasting, and resource allocation.
• Demonstrated ability to translate complex technical concepts and requirements into clear, actionable deliverables for both technical and non-technical stakeholders.
• Proven experience managing cross-functional stakeholder relationships across engineering, product management, design, and business operations with the ability to drive accountability without formal authority.
• Advanced skills in dependency mapping, critical path analysis, and risk identification and mitigation across complex, multi-team technical programs.
• Experience with vendor management activities including development of RFPs, RFQs, and RFIs; contract review (MSAs, SOWs, subscription agreements); and contractor onboarding.
• Formal training or working knowledge of the Software Development Lifecycle (SDLC) and application development practices required.
• Six Sigma Green Belt or Black Belt certification preferred; demonstrated experience applying lean process improvement methodologies.
• Extreme learning agility with the ability to quickly grasp evolving technologies, frameworks, and system architectures in a fast-paced digital environment.
• High emotional intelligence (EQ) with the ability to identify team dynamics, manage conflict, and maintain composure under pressure in a high-stakes delivery environment.
• Strong proficiency in Microsoft Office Suite (Outlook, Excel, Word, PowerPoint, Visio, Access) required.
• Regular, predictable, full attendance is an essential function of the job.
• Willingness to travel as necessary, work the required schedule, and work at the specific location required.
• Successful completion of a Penske employment application, background investigation (including past employment, education, and criminal history), and drug screening are required.

Physical Requirements:

The physical and mental demands described here are representative of those that must be met by an associate to successfully perform the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

• The associate will be required to: read; communicate verbally and/or in written form; remember and analyze certain information; and remember and understand certain instructions or guidelines.
• While performing the duties of this job, the associate may be required to stand, walk, and sit. The associate is frequently required to use hands to touch, handle, and feel, and to reach with hands and arms. The associate must be able to occasionally lift and/or move up to 25lbs/12kg.
• Specific vision abilities required by this job include close vision, distance vision, peripheral vision, depth perception and the ability to adjust focus.

Penske is an Equal Opportunity Employer.

To Learn More

• About Penske’s Digital Products: https://www.pensketruckleasing.com/digital-experience/
• About Penske: https://www.gopenske.com/our-company/

This position was posted by Penske Truck Leasing Corporate Headquarters (Reading, PA). Apply through the official website using the link on this page.