Fleet Supervisor

Fleet Supervisor

Position Type Full Time

Description

Fleet 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

Qualifications

What 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

• 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 View email address on click.appcast.io with the subject line Fleet Operations Supervisor