Fleet Director- Remote

The Director of Fleet Management & Operations is responsible for the strategic leadership, operational performance, and financial management of a large-scale, multi-location fleet (1,000+ assets) within a primarily leased and/or mixed ownership environment. This role drives fleet operations as a competitive advantage by maximizing asset uptime, ensuring regulatory compliance, and optimizing total cost of ownership (TCO). This leader partners closely with Operations, Finance, Safety, and Supply Chain to align fleet strategy with business growth, while building scalable systems, high-performing teams, and data-driven decision-making capabilities.

Key Responsibilities

Strategic Fleet & Lifecycle Management

• Develop and execute a 1-5 year fleet strategy aligned with company growth, operational demand, and financial objectives
• Oversee vehicle and equipment acquisition, specification, utilization, replacement cycles, and disposal strategies
• Optimize fleet composition (leased vs. owned) to balance flexibility, cost efficiency, and operational performance
• Evaluate and implement emerging technologies, electrification opportunities, and sustainability initiatives where applicable

Operational Excellence & Uptime

• Ensure maximum fleet uptime, reliability, and service quality across all locations
• Standardize and enforce preventive maintenance programs, shop operations, and repair processes
• Drive continuous improvement initiatives to reduce downtime, increase asset utilization, and improve field service delivery
• Oversee maintenance authorization, repair quality, and spend controls

Financial Leadership & Cost Optimization

• Own fleet-related financial performance, including budgeting, forecasting, OpEx, and CapEx planning (where applicable)
• Analyze and optimize Total Cost of Ownership (TCO), cost per mile/hour, and lifecycle costs
• Identify and execute cost-reduction initiatives without compromising safety or service levels
• Evaluate ROI on new assets, technologies, and vendor programs

Leasing, Vendor & Asset Management

• Serve as executive owner of relationships with leasing companies, OEMs, maintenance providers, and national vendors
• Negotiate contracts, pricing, warranties, and service-level agreements (SLAs)
• Monitor vendor performance and ensure accountability to KPIs and cost expectations
• Oversee asset tracking, telematics platforms, and CMMS/maintenance systems
• Lead parts procurement strategies, inventory control, and warranty recovery programs

Fuel, Telematics & Data Analytics

• Oversee fuel programs, fuel card controls, and initiatives to reduce consumption and fraud
• Leverage telematics and analytics to improve routing, driver behavior, utilization, and maintenance planning
• Establish reporting frameworks and dashboards to support real-time, data-driven decision-making

Safety & Regulatory Compliance

• Ensure full compliance with DOT, FMCSA, OSHA, and all federal, state, and local regulations
• Partner with Safety leadership to drive accident reduction and enforce driver safety programs
• Maintain audit readiness and ensure accurate documentation for inspections and compliance reporting
• Track and improve key safety metrics, including accident frequency and severity

Cross-Functional Leadership

• Partner with Operations to ensure fleet availability aligns with field and customer requirements
• Collaborate with Finance on forecasting, accruals, and long-term capital planning
• Support Supply Chain and Procurement initiatives related to fleet and equipment sourcing
• Act as a strategic advisor to executive leadership on fleet performance and opportunities

Leadership & Team Development

• Lead and develop multi-region fleet, maintenance, and technical teams
• Build a high-performance culture centered on accountability, safety, and continuous improvement
• Establish scalable processes, standard operating procedures, and performance management systems
• Drive organizational capability in analytics, technology adoption, and operational execution

Key Performance Indicators (KPIs)

• Total Cost of Ownership (TCO) / cost per mile or hour
• Fleet uptime and downtime percentage
• Preventive maintenance compliance rate
• Asset utilization rates
• Maintenance and repair cost performance
• Fuel efficiency and fuel cost management
• Vendor SLA performance
• Accident frequency and severity
• Budget vs. actual (OpEx and CapEx)
• Regulatory compliance and audit outcomes

Qualifications

Experience

• 10-15+ years of progressive experience in fleet, transportation, logistics, or equipment management
• Minimum 5+ years in senior leadership (Director, VP, or equivalent)
• Proven success managing large, multi-location fleets (1,000+ assets preferred)
• Strong experience with leased fleets, vendor management, and cost optimization

Education

• Bachelor's degree in Business, Supply Chain, Engineering, Logistics, or related field required
• MBA or advanced degree preferred

Technical Expertise

• Deep knowledge of fleet operations, maintenance programs, and lifecycle management
• Experience with telematics, fuel systems, and CMMS/fleet management platforms
• Strong understanding of DOT, FMCSA, OSHA, and related compliance requirements
• Certified Equipment Manager (CEM) or similar certification preferred

Leadership Profile

• Strategic thinker with the ability to execute at scale
• Strong financial and analytical acumen with a data-driven mindset
• Skilled negotiator with extensive vendor and contract management experience
• Proven ability to influence cross-functional stakeholders and executive leadership
• Results-oriented leader focused on accountability, efficiency, and continuous improvement

Preferred Experience

• Experience in field services, construction, transportation, or logistics industries
• Background in private equity-backed, high-growth, or operationally complex environments
• Experience leading fleet transformation initiatives (technology, centralization, or cost restructuring)

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