Lead Director – Middle Mile

This is a fully remote position, open to applicants in Alabama, +45 more states.

📋 Description

• Lead and enhance the Middle Mile Center of Excellence, which includes Fleet Asset Management, Control Tower, and Analytics.

• Develop an organizational structure, performance expectations, and talent strategies that align with enterprise priorities.

• Cultivate a culture centered on safety, accountability, innovation, and operational excellence.

• Take ownership of the fleet lifecycle strategy, covering procurement, utilization, maintenance, replacement planning, and vendor management.

• Optimize asset performance, cost structure, capital investments, and the total cost of ownership.

• Ensure adherence to safety, regulatory, and environmental standards.

• Oversee centralized transportation planning, routing, dispatch, and exception management.

• Create a single source of truth for transportation execution across Private and Dedicated Fleet operations.

• Enhance service performance, route efficiency, asset utilization, and network visibility through process and technology solutions.

• Develop enterprise performance management frameworks that link cost, service, and productivity metrics to actionable outcomes.

• Standardize KPI governance, reporting, and performance routines throughout the network.

• Drive continuous improvement initiatives aimed at network optimization, cost reduction, and operational efficiency.

• Assess and implement advanced analytics, automation, and AI-enabled solutions for forecasting, routing, and decision-making.

• Establish operating models, accountability mechanisms, and standardized performance reviews across the network.

• Lead executive-level performance reviews and escalation processes.

• Act as a strategic advisor to senior Middle Mile leadership.

• Collaborate with Distribution Centers, Supply Chain, Finance, Procurement, and Technology teams.

• Influence priorities, resource allocation, and key business decisions within a complex, matrixed organization.

⛳️ Requirements

• A minimum of 10 years of progressive leadership experience in transportation, logistics, or supply chain.

• Proven experience with continuous improvement and structured methodologies.

• Familiarity with DOT/FMCSA regulations and transportation compliance.

• Experience in data analytics, KPI governance, and financial performance management.

• Proficiency with analytics visualization tools.

• Willingness to travel up to 15%.

• Background in multi-site retail or distribution environments.

• Demonstrated experience with Trimble Appian.

• Strong skills in routing software technology, including Omnitracs/Trimble.

• Experience in leading centralized functions, Centers of Excellence, or operational excellence teams.

• Proficient in Power BI, SQL, and network modeling platforms.

• Knowledge of AI and automation applications in transportation execution.

• Lean / Six Sigma certification or a background in continuous improvement.

• Extensive expertise in fleet operations and asset management.

• Proven track record in transportation routing and network planning.

• Demonstrated ability to achieve measurable business results in a matrixed, multi-site environment.

• Strong strategic thinking and enterprise-level vision.

• Data-driven decision-making capabilities and analytical rigor.

• Executive presence with strong communication and leadership influence skills.

• Experience in cross-functional leadership within a matrixed environment.

• Ability to exercise sound judgment/problem-solving, think innovatively, and collaborate effectively.

• A Master’s degree is preferred.

• High School Diploma or GED is required.

🏝️ Benefits

• CVS Health bonus, commission, or short-term incentive program.

• Award target in the company’s equity award program.

• Comprehensive medical coverage.

• Dental coverage.

• Vision coverage.

• Paid time off.

• Retirement savings options.

• Wellness programs.

• Additional resources supporting physical, emotional, and financial well-being.