Director of Fleet Services - Main Office

Director of Fleet Services

About the Organization Case Facility Management Solutions is an industry leader in exterior facility services, focused on snow and landscape services. Case FMS services over 30,000 small and large commercial sites across 50 states and we continue to grow at a rapid pace. If you are looking for an opportunity to join a dynamic team in a company that is continuously expanding, visit our website at  Apply today to learn why Case's employees describe a typical day as challenging, exciting, rewarding and fun!

The Director of Fleet Services provides strategic and operational leadership for Case FMS's fleet operations across the United States and Canada. This role oversees the performance, safety, compliance, and optimization of all company-owned and leased vehicles and equipment, ensuring reliable service delivery to support core operations. The Director leads preventive maintenance programs, vendor partnerships, and fleet innovation initiatives while managing a high-performing team of mechanics and fleet professionals.

• Lead and oversee fleet operations across U.S. and Canadian business units, ensuring consistent policies, compliance, and service standards in both geographies.
• Direct all aspects of fleet maintenance, repair, safety inspections, and compliance with DOT, provincial, and federal regulations.
• Develop, implement, and continuously refine a preventive maintenance and lifecycle management program that maximizes uptime and controls costs.
• Maintain accountability for fleet inventory, expenditures, and fuel usage with robust tracking, reporting, and audit-ready documentation.
• Partner with Operations leadership to ensure fleet availability and mobilization for seasonal demand (snow, landscaping, and other ancillary services).
• Establish vendor and supplier relationships, negotiate contracts, and oversee third-party service providers.
• Collaborate with Finance on annual fleet budget planning, forecasting, and cost analysis; identify opportunities for savings and efficiency gains.
• Provide monthly executive reporting to COO on inspections, maintenance KPIs, compliance status, and overall fleet readiness.
• Lead the fleet safety program, including vehicle telematics, cab camera systems, and driver engagement initiatives.
• Partner with IT/Technology to leverage Fleet Management Information Systems (FMIS), GPS/telematics, and analytics dashboards to drive decisions.
• Oversee fleet mobilization and logistics planning during major weather events or emergencies.
• Recruit, develop, and lead the fleet team; ensure accountability through training, performance management, and succession planning.

• Deep knowledge of U.S. DOT, Canadian transportation compliance, and safety regulations.
• Proven expertise in multi-region fleet management, including heavy equipment, trucks, and specialized service vehicles.
• Strong financial and analytical skills with the ability to manage budgets and drive cost optimization.
• Demonstrated leadership in building and managing cross-functional teams.
• High proficiency with fleet technology platforms, telematics, and reporting tools.
• Bachelor’s degree in Business, Operations, Logistics, or related field, preferred.
• 8–12 years of progressive fleet management experience, preferably in multi-site or multi-country operations.
• Experience with subcontractor and vendor management strongly preferred.

Full-Time/Part-Time Full-Time Location Main Office Number of Openings 1

We are an equal employment opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, disability status, protected veteran status or any other characteristic protected by law.

This position is currently accepting applications.

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