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Job description
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.
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.
Previous experience 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 of 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.
Thank you for your interest in opportunities with CWR!
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Accessibility: If you need an accommodation as part of the employment process please contact Human Resources at (850) 385‑5060.
In compliance with Federal and State equal employment opportunity laws, qualified applicants are considered for all positions without regard to race, color, religion, sex, national origin, age, marital status, veteran status, non‑job related disability, or any other protected group status. If you want to view the Know Your Rights: Workplace Discrimination is Illegal poster, click HERE. If you want to view the Pay Transparency Policy Statement, please click the link: English.
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Worksite address
pensacola, FL, 32573, US
Who can apply
Review the original listing for work authorization, qualifications and employer requirements.