DIRECTOR OF FLEET OPERATIONS
CWR Contracting, Inc., is seeking a Director of Fleet Operations. The Director of Fleet Operations oversees the full lifecycle management of 2100+ fleet vehicles and heavy equipment across 9 locations: Daytona, Pensacola, Freeport, Panama City, Hosford, Plant City, Wildwood, and Palm City, Florida.
Essential Job Responsibilities:
- Develop and execute fleet strategy, including capital forecasting, replacement modeling, and right-sizing.
- Lead procurement and upfitting of vehicles, trailers, and heavy equipment; coordinate branding, telematics, and field deployment.
- Manage vendor relationships, leasing agreements, warranty claims, and recall programs.
- Oversee internal repair facilities and external vendor programs to optimize uptime and cost efficiency.
- Maintain compliance with DOT, FMCSA, CDL, and state registration/title requirements across all jurisdictions.
- Administer fleet telematics and driver behavior systems, including safety analytics, DVIRs, and dash cameras.
- Maintain centralized fleet census and asset visibility, including VIN-level inventory, utilization, and location data.
- Track fleet KPIs
- Collaborate with Accounting on lifecycle modeling, cost analysis, and budgeting.
- Partner with Safety on incident investigations, coaching, and root cause mitigation
- Provide strong leadership and foster collaboration by partnering with branch-level teams to align resources, drive performance, and ensure consistent execution of organizational goals.
- Strategic thinker with ability to balance long-term planning and daily operations.
- Strong organizational and analytical skills with attention to detail.
- Collaborative partner with the ability to influence cross-functional teams.
- Resilient, adaptable, and capable of thriving in a high-demand environment.
- Other duties as assigned
Job Requirements:
- Bachelor’s degree in Business, Supply Chain, Logistics, or related field (preferred).
- 10+ years of progressive fleet management experience, ideally within construction industries.
- Demonstrated expertise in DOT/FMCSA compliance, procurement, and vendor management.
- Proficiency in fleet technologies (e.g., Geotab, dash cams, fuel card systems).
- Previous experience with managing fleet personnel, including staffing requirements, scheduling, performance management, and compliance with company and regulatory standards.
- Strong financial acumen with experience in capital planning and cost control.
- Bilingual abilities are a plus
- Working knowledge in Industrial Safety and environmental compliance reporting
- Solid technical and analytical skills, mechanical skills and problem-solving ability
- Strong recordkeeping and organization skills with attention to detail
- Strong computer skills including Microsoft Word, Excel, Outlook; ability to master local operational software
- Out of town travel as required by company needs
- Must be able to meet company MVR requirements and have a valid Florida driver’s license
- Employer conducts drug testing and background check
We offer competitive wages and fringe benefits. Company vehicle included. Relocation expenses will be considered. Location negotiable within company’s division footprint.
EOE/AA, DFWP, We Honor Those Who Have Served.
Position open until filled.
Accessibility: If you need an accommodation as part of the employment process please contact Human Resources at (850) 385-5060.
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