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Director of Fleet Operations

CWR Contracting, Inc.
Tallahassee, FL Full Time
POSTED ON 3/16/2026 CLOSED ON 4/15/2026

What are the responsibilities and job description for the Director of Fleet Operations position at CWR Contracting, Inc.?

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.

Salary.com Estimation for Director of Fleet Operations in Tallahassee, FL
$112,926 to $151,620
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