Fleet Operations Director

Fleet Operations DirectorLeeSar Cooperative Services of FloridaLocation: Southwest FloridaAre 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 MattersAt 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 LeadStrategic & 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 coordinationSafety & Regulatory Excellence Ensure full DOT, OSHA, and transportation compliance Lead safety initiatives, audits, and corrective action plans Oversee vehicle inspections, maintenance programs, and documentationFinancial & Resource Management Partner on annual budgeting and cost control initiatives Monitor fuel usage and fleet expenses Lead vehicle acquisition, leasing, and lifecycle strategyTalent Development Build and mentor high-performing supervisors and drivers Oversee hiring, training, performance management, and accountability Foster a culture of professionalism, service, and continuous improvementPerformance & Quality Monitor KPIs including delivery accuracy, driver safety, and vehicle performance Identify operational improvement opportunities Partner cross-functionally to enhance service delivery and customer satisfactionWhat 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 licensePreferred: 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 packageBenefits PackageLeeSar 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 careers@ with the subject line Fleet Operations Director

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