Vice President, Technology - Transportation ( Logistics

Position: Vice President, Technology - Transportation (Penske Logistics)
** Why This Role:*
* 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

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* Position Summary:

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* 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.

** Major Responsibilities:*
* ** Technology Strategy & Roadmap*
* - 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.

** Product & Development Leadership*
* - 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.

** Business Partnership & Value Delivery*
* - 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.

** Platform, Data & Innovation*
* - 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 (project
44, Fourkites, DAT, etc.)

- Define API strategy and ecosystem integrations to enable seamless connectivity with shippers, carriers, and 3PL partners.

** Operational Excellence & Governance*
* - Own technology budget, including OpEx/Cap Ex 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.*
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* Required Qualifications:

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* - 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…