About this role
Job DetailsPosition Type: Full TimeFleet Supervisor
Department: Fleet Operations
Location: Fort Myers, FL | Status: Onsite
Keep Critical Healthcare Operations Moving
LeeSar and Cooperative Services of Florida (CSF) are seeking a Fleet Supervisor to oversee and optimize the performance of our vehicle fleet supporting healthcare operations across Southwest Florida.
This role is ideal for a hands-on leader who thrives in a fast-paced, operational environment and is passionate about safety, compliance, and efficiency. You will serve as the central point of contact for fleet operations across multiple service lines, ensuring vehicles are safe, compliant, and ready to support time-sensitive healthcare deliveries.
What You’ll Do
Fleet Operations & Asset Management
Oversee full lifecycle management of fleet vehicles, including acquisition, deployment, maintenance, and replacement
Maintain accurate records for registrations, insurance, licensing, and vehicle assignments
Serve as the primary contact for fleet operations across Courier, Central Fill, EMS, Culinary, and other service lines
Maintenance & Vehicle Readiness
Coordinates preventive maintenance, repairs, and recalls with internal teams and external vendors
Monitor vehicle usage, mileage, and condition to minimize downtime
Investigate recurring mechanical issues and implement solutions
Compliance & Safety
Ensure compliance with DOT, OSHA, HIPAA, and all applicable regulations
Maintain audit-ready documentation for inspections and regulatory reviews
Support accident investigations and reinforce safe driving practices
Fleet Technology & Cost Management
Oversee telematics systems (GPS, cameras, tracking platforms) to monitor performance and safety trends
Manage fuel card programs, toll systems, and expense tracking
Analyze data related to utilization, fuel consumption, and maintenance costs
Leadership & Collaboration
Partner with Dispatch, Operations, Finance, and vendors to ensure seamless service delivery
Support driver onboarding and training related to fleet systems and safety
Provide coaching, performance feedback, and real-time issue resolution
Drive continuous improvement in fleet performance, safety, and efficiency
QualificationsWhat You Bring
Required
High School Diploma or GED
Minimum of 3 years of experience in fleet operations, vehicle management, or transportation
Valid driver’s license with acceptable driving record
Preferred
Associate or Bachelor’s degree in Business, Transportation, Supply Chain, or related field
Experience in healthcare, pharmaceutical, or regulated delivery environments
Key Strengths
Strong knowledge of vehicle maintenance and compliance requirements
Experience with telematics systems and fleet management software
Analytical mindset with ability to interpret operational data
Strong organizational and problem-solving skills
Ability to manage multiple priorities in a fast-paced environment
Flexibility to respond to urgent operational needs
Why Join LeeSar & CSF
At LeeSar and CSF, our fleet operations are critical to supporting hospitals and healthcare systems throughout Southwest Florida.
As a Fleet Supervisor, you will
Play a vital role in ensuring timely delivery of critical healthcare supplies
Lead operational improvements that directly impact service reliability
Work in a collaborative, mission-driven environment
Grow your leadership and operational expertise
Benefits Package
LeeSar and CSF offers a comprehensive benefits package that includes an on-site health clinic, annual bonus program, an HDHP plan at zero cost for associate-only coverage, employer contributions to HSA and cost-sharing at all coverage levels, employer-paid disability and group life insurance, and a 401(k) plan with up to a 5% employer match and immediate vesting, plus a Roth option. Additional benefits include dental, vision, and voluntary plans, tuition reimbursement, professional development opportunities, nine paid holidays, and a generous PTO bank.
At LeeSar and CSF, our Associates drive the success of our member hospitals and clinical partners. We proudly operate as an Equal Opportunity Employer and maintain a Drug-Free/Tobacco-Free Workplace.
Interested candidates may request the full job description by emailing [email protected] with the subject line Fleet Operations Supervisor
Tired of cold applications?
Sign up with Clera and we'll reach out the moment a role actually fits you — no more spraying applications into the void.
Know someone who'd be great for this?