Vice President, Technology - Transportation (Penske Logistics)

Penske • Beachwood, OH

6d • Hybrid

About The Position

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.

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.

Requirements

• 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
• Serves as the senior technology executive responsible for envisioning, building, and operating the full suite of technology.
• Owns the technology roadmap across Dedicated Fleet, Managed Transportation, Freight Brokerage, and related transportation lines of business.
• Partnering with business unit leaders to identify market-defining technology investments
• Leading large development and product teams to deliver with speed and quality.
• Key voice in enterprise architecture decisions, technology due diligence, and the company's digital transformation agenda.
• 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

Nice To Haves

• AI/ML
• autonomous vehicle integration
• real-time visibility platforms
• legacy modernization
• cloud migration programs
• predictive analytics
• AI-powered decision support
• automation
• machine learning models for pricing/routing
• integration with external data networks (project44, Fourkites, DAT, etc.)
• API strategy
• ecosystem integrations
• cybersecurity standards
• data privacy (CCPA, SOX)
• regulatory compliance
• disaster recovery
• business continuity
• SLA management

Responsibilities

• 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

Benefits

• Competitive total compensation including base, annual bonus, and long-term incentive plan
• Relocation assistance may be available for qualified candidates

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed