Lead Director – Middle Mile

CVS Health

. Lead and develop the Middle Mile Center of Excellence, encompassing Fleet Asset Management, Control Tower, and Analytics .

Posted 10/5/2026full-timeRemote • United StatesSenior💰 $100,000 - $231,540 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates extensive expertise in Fleet Asset Management, Transportation Compliance, and Data Analytics, with a strong focus on optimizing operational efficiency and cost reduction. Proven ability to lead cross-functional teams and implement continuous improvement initiatives in a complex, multi-site environment.

Highest-signal resume keywords

Fleet Operations ManagementTransportation Compliance (DOT/FMCSA)Data Analytics and KPI GovernanceLean / Six Sigma CertificationRouting Software Technology (Omnitracs/Trimble)

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Fleet Asset ManagementData AnalyticsKPI GovernanceFinancial Performance ManagementRouting Software TechnologyNetwork PlanningAdvanced AnalyticsAutomation ApplicationsSQLPower BI

Soft Skills

Strategic ThinkingExecutive PresenceStrong Communication SkillsCross-Functional LeadershipProblem Solving

Tools & Technologies

Trimble AppianOmnitracsPower BISQLAnalytics Visualization Tools

Certifications & Qualifications

Lean / Six Sigma Certification

Industry Keywords

TransportationLogisticsSupply ChainContinuous ImprovementOperational Excellence

Tech Stack

Tools & technologies

SQL

About the role

Key responsibilities & impact

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
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
Develop enterprise performance management frameworks linking cost, service, and productivity metrics to actionable outcomes
Standardize KPI governance, reporting, and performance routines across the network
Lead continuous improvement initiatives focused on network optimization, cost reduction, and operational efficiency
Evaluate 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
Serve as a strategic advisor to senior Middle Mile leadership
Partner with Distribution Centers, Supply Chain, Finance, Procurement, and Technology teams
Influence priorities, resource allocation, and key business decisions across a complex, matrixed organization

Requirements

What you’ll need

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, including Omnitracs/Trimble
Experience leading centralized functions, Centers of Excellence, or operational excellence teams
Experience with Power BI, SQL, and network modeling platforms
Familiarity with AI and automation applications in transportation execution
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 and enterprise-level vision
Data-driven decision making and analytical rigor
Executive presence and strong communication and leadership influence skills
Cross-functional leadership in a matrixed environment
Ability to demonstrate sound judgement/problem solving, think innovatively, and collaborate effectively
Master's degree listed as a preferred qualification
High School Diploma/GED

Benefits

Comp & perks

CVS Health bonus, commission or short-term incentive program
Award target in the company’s equity award program
Medical coverage
Dental coverage
Vision coverage
Paid time off
Retirement savings options
Wellness programs
Other resources supporting physical, emotional, and financial well-being