Vice President Technology Leadership Jobs (NOW HIRING)

This is a rare opportunity to shape technology strategy at scale — leading one of the most consequential technology transformations in the $800B U.S. trucking and logistics industry. The successful candidate will have the autonomy, budget, and executive sponsorship to build best‑in‑class transportation technology platforms that directly drive competitive advantage and shareholder value.

• Lead technology at one of the largest transportation companies in North America
• Significant scope: enterprise‑wide platform ownership across multiple high‑growth business lines
• Executive team access and meaningful seat at the strategic table
• Competitive total compensation including base, annual bonus, and long‑term incentive plan
• High‑impact, mission‑critical work in an industry undergoing rapid technology‑driven disruption

The Vice President of Technology – Transportation serves as the senior technology executive responsible for envisioning, building, and operating the full suite of technology. This executive owns the technology roadmap across Dedicated Fleet, Managed Transportation, Freight Brokerage, and related transportation lines of business.

This role bridges strategy and execution — partnering with business unit leaders to identify market‑defining technology investments, while leading large development and product teams to deliver with speed and quality. The VP will be a key voice in enterprise architecture decisions, technology due diligence, and the company's digital transformation agenda.

This position is based in our Penske Logistics development center in Beachwood, OH. This is an in‑office position, at least 4 days a week. Relocation assistance may be available for qualified candidates.

• Define and own the multi‑year technology roadmap for transportation platforms, aligned to business growth, operational efficiency, and competitive differentiation.
• Evaluate emerging technologies (AI/ML, autonomous vehicle integration, real‑time visibility platforms) for strategic fitness and investment prioritization.
• Lead build‑vs‑buy analysis and drive vendor selection for enterprise transportation technology investments.
• Serve as the technology voice in executive and senior‑level strategy discussions.

• Lead and grow a high‑performing organization of 25–100+ developers, architects, product managers, and technical program managers.
• Establish IT development excellence standards including CI/CD pipelines, code quality, testing automation, and system reliability targets.
• Drive agile/scaled agile delivery practices, ensuring on‑time execution of major platform initiatives.
• Build a strong technical culture that attracts, retains, and develops top‑tier technology talent.

• Partner with SVPs, VPs and GMs of Dedicated Fleet, Managed Transportation, and Brokerage business units to co‑own technology‑enabled growth initiatives.
• Translate complex operational challenges into technology solutions — from driver retention tools to carrier pricing algorithms.
• Establish and govern technology investment governance, ROI tracking, and portfolio prioritization frameworks.
• Represent technology in customer‑facing engagements, RFPs, and strategic account retention.

• Oversee the evolution of the company's TMS and visibility platforms — including legacy modernization and cloud migration programs.
• Drive the enterprise data strategy, enabling real‑time freight intelligence, predictive analytics, and AI‑powered decision support.
• Lead innovation initiatives including automation, machine learning models for pricing/routing, and integration with external data networks (project44, Fourkites, DAT, etc.).
• Define API strategy and ecosystem integrations to enable seamless connectivity with shippers, carriers, and 3PL partners.

• Own technology budget, including OpEx/CapEx planning, vendor negotiations, and cost optimization.
• Establish and enforce technology governance policies, including cybersecurity standards, data privacy (CCPA, SOX), and regulatory compliance.
• Lead disaster recovery, business continuity, and SLA management for mission‑critical transportation systems.
• Drive continuous improvement of system uptime, platform performance, and end‑user experience metrics.
• Other projects and tasks as assigned.

• Bachelor's degree in Computer Science, Engineering, Information Systems, or related field required.
• Master's degree in Technology Management, MBA, or related field strongly preferred.
• 15+ years of progressive technology leadership experience, with 8+ years in senior technology executive roles (VP, SVP, CTO equivalent).
• Demonstrated success leading technology organizations at companies with $1B+ in revenue, preferably in transportation, logistics, supply chain, or asset‑heavy industries.
• Deep experience with TMS platforms (e.g., McLeod, TMW, Oracle TMS, MercuryGate, Trimble), freight brokerage systems, and fleet management technology.
• Track record of leading large‑scale cloud migration, platform modernization, or digital transformation programs.
• Experience managing P&L responsibilities or large technology budgets ($50M+) with direct accountability for ROI.
• Strong working knowledge of cloud platforms (AWS, Azure, or GCP), microservices architecture, and API‑first design principles.
• Familiarity with transportation technology ecosystem: ELD/telematics (Samsara, Omnitracs), visibility platforms (project44, Fourkites), load boards (DAT, Truckstop), EDI standards.
• Hands‑on understanding of data engineering, data warehousing, and applied machine learning — particularly for pricing, routing, and demand forecasting use cases.
• Knowledge of transportation regulations and compliance requirements (FMCSA, HOS, ELD mandate, IFTA).
• Proven ability to lead, inspire, and scale diverse technology organizations of 50+ associates across IT development, product, and architecture functions.
• Executive communication skills with the ability to engage C‑suite, SVPs, customers, and operational teams with equal credibility.
• Strong business acumen with the ability to connect technology investments to measurable revenue growth, cost reduction, and market advantage.
• Experience in M&A technology due diligence and post‑merger technology integration.
• Regular, predictable, full attendance is an essential function of the job.

• Experience with brokerage technology including load matching algorithms, carrier scoring, and margin optimization systems.
• Familiarity with autonomous trucking technology, electric vehicle fleet integration, or advanced ADAS systems.
• Experience building or scaling proprietary shipper and carrier‑facing applications with significant user adoption.
• Active involvement in industry associations (ATA, TIA, CSCMP, Gartner Supply Chain).
• Prior experience as CTO or divisional technology head in a publicly traded logistics company.

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