Job Description
Fleet Operations Director
LeeSar | Cooperative Services of Florida
Location: Southwest Florida
Are you a strategic transportation leader who thrives in fast-paced, mission-driven environments?
LeeSar is seeking a dynamic Fleet Operations Director to lead and optimize our fleet and dispatch operations supporting hospitals, medical offices, pharmacy services, EMS, culinary, and distribution operations across Southwest Florida.
This is a high-impact leadership role where operational excellence directly supports patient care.
Why This Role Matters
At LeeSar, our fleet operations are critical to ensuring life-saving products, pharmaceuticals, and essential supplies are delivered safely, accurately, and on time. As Fleet Operations Director, you will shape strategy, drive performance, and lead a team that keeps healthcare moving.
What You’ll Lead
Strategic & Operational Leadership
- Direct all fleet and courier operations across multiple service lines
- Optimize routing, staffing, scheduling, and vehicle utilization
- Leverage telematics and dispatch systems to drive performance
- Oversee emergency/stat delivery coordination
Safety & Regulatory Excellence
- Ensure full DOT, OSHA, and transportation compliance
- Lead safety initiatives, audits, and corrective action plans
- Oversee vehicle inspections, maintenance programs, and documentation
Financial & Resource Management
- Partner on annual budgeting and cost control initiatives
- Monitor fuel usage and fleet expenses
- Lead vehicle acquisition, leasing, and lifecycle strategy
Talent Development
- Build and mentor high-performing supervisors and drivers
- Oversee hiring, training, performance management, and accountability
- Foster a culture of professionalism, service, and continuous improvement
Performance & Quality
- Monitor KPIs including delivery accuracy, driver safety, and vehicle performance
- Identify operational improvement opportunities
- Partner cross-functionally to enhance service delivery and customer satisfaction
What You Bring
- Minimum 5+ years of logistics, transportation, or fleet operations experience
- 5+ years of progressive leadership experience
- Strong knowledge of DOT, OSHA, and transportation regulations
- Experience with fleet telematics and dispatch systems
- Demonstrated financial oversight and budgeting experience
- Data-driven decision-making and KPI analysis skills
- Valid, clean driver’s license
Preferred:
- Bachelor’s degree in Business, Supply Chain, or related field
- Experience in healthcare logistics or regulated transportation environments
- Multi-site fleet leadership experience
Why Join LeeSar?
- Mission-driven organization supporting healthcare systems
- Executive-level visibility and impact
- Opportunity to modernize and optimize fleet operations
- Collaborative leadership environment
- Competitive compensation and benefits package
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 Director