Transportation Center of Excellence, Lead Director - Middle Mile

We’re building a world of health around every individual — shaping a more connected, convenient and compassionate health experience. At CVS Health®, you’ll be surrounded by passionate colleagues who care deeply, innovate with purpose, hold ourselves accountable and prioritize safety and quality in everything we do. Join us and be part of something bigger – helping to simplify health care one person, one family and one community at a time.

The Lead Director, Transportation Center of Excellence, Middle Mile is a senior transportation leader responsible for driving performance, governance, and strategic execution across CVS Health's middle mile transportation network. This role brings together Fleet Asset Management, Control Tower oversight, and network analytics to improve financial results, service performance, and operational effectiveness across both Private Fleet and Dedicated Fleet operations.

Reporting to the Executive Director, you will serve as a strategic partner to transportation operations leadership, providing centralized oversight, insights, and decision support while maintaining appropriate separation from day-to-day field execution. Through a disciplined approach to performance management, network optimization, and process standardization, this role identifies opportunities to improve asset utilization, routing efficiency, and overall transportation effectiveness.

This position leads a team and collaborates across multiple business functions, influencing leaders, managers, and key internal and external stakeholders. The role requires effective partnership building, strong execution under tight deadlines, and the ability to align people, processes, and systems around shared objectives. Success in this role depends on balancing strategic thinking with operational discipline, fostering innovation, and delivering sustainable year-over-year improvements across the transportation network.

An ideal candidate combines deep transportation and supply chain expertise with strong business acumen and a proven track record in analytics and continuous improvement. This leader will establish scalable processes, leverage data-driven insights to optimize network performance, and deliver measurable operational and financial results while supporting broader Supply Chain and enterprise priorities.

• Lead and develop the Middle Mile Center of Excellence, encompassing Fleet Asset Management, Control Tower, and Analytics.
• Establish organizational structure, performance expectations, and talent strategies aligned with enterprise priorities.
• Foster a culture of safety, accountability, innovation, and operational excellence.

• Own fleet lifecycle strategy, including procurement, utilization, maintenance, replacement planning, and vendor management.
• Optimize asset performance, cost structure, capital investments, and total cost of ownership.
• Ensure compliance with safety, regulatory, and environmental standards.

• Lead centralized transportation planning, routing, dispatch, and exception management activities.
• Establish a single source of truth for transportation execution across Private and Dedicated Fleet operations.
• Improve service performance, route efficiency, asset utilization, and network visibility through process and technology solutions.

• Establish operating models, accountability mechanisms, and standardized performance reviews across the network.
• Align centralized planning and analytics functions with field execution teams to drive consistent results.
• Lead executive-level performance reviews and escalation processes.

• Serve as a strategic advisor to senior Middle Mile leadership.
• Partner with Distribution Centers, Supply Chain, Finance, Procurement, and Technology teams to drive network performance.
• Influence priorities, resource allocation, and key business decisions across a complex, matrixed organization.
  

• Minimum 10 years of progressive leadership experience in transportation, logistics, or supply chain
• Experience with continuous improvement and structured methodology
• Experience with DOT/FMCSA regulations and transportation compliance
• Experience with data analytics, KPI governance, and financial performance management

• Experience with analytics visualization tools
• Travel up to 15%

• Experience in multi-site retail or distribution environments
• Demonstrated Trimble Appian experience; strong competency with routing software technology (Omnitracs/Trimble)
• Leading centralized functions, Centers of Excellence, or operational excellence teams
• Experience with Power BI, SQL, network modeling platforms
• Familiarity with AI and automation applications in transportation execution — including AI-enabled control towers, predictive ETAs, and automated exception management
• Lean / Six Sigma certification or continuous improvement background
• Strong expertise in fleet operations and asset management
• Proven expertise in transportation routing and network planning
• Demonstrated ability to deliver measurable business results in a matrixed, multi-site environment
• Strategic thinking – enterprise-level vision and long-range planning
• Data-driven decision making – analytical rigor applied to performance management
• Executive presence – strong communication and leadership influence skills
• Cross-functional leadership - ability to align and lead in a matrixed environment
• Demonstrated ability to deliver measurable business results
• Ability to demonstrate sound judgement/problem solving, think innovatively and collaborate effectively with others
• Master's degree

The typical pay range for this role is: