Fleet and Delivery Manager

Join to apply for the Fleet and Delivery Manager role at Site One Landscape Supply
.

Candidates can live anywhere in Maryland, Washington D.C., or Virginia.

The Fleet & Delivery Manager leads fleet operations, delivery execution, and equipment oversight across multiple locations. This role ensures asset safety, compliance, and performance while owning the fleet and delivery P&L. The manager provides strategic oversight of the delivery process—ensuring teams, systems, and resources are aligned with the Delivery Excellence framework—and leads Dispatch Supervisors who manage driver teams in a centralized fleet model.

• Fleet Management, Safety, & Compliance
  • Oversee procurement, transfers, maintenance cycles, repairs, disposals, and replenishment of all delivery and facility equipment.
  • Ensure all assets meet regulatory and operational standards, including DOT compliance, telematics usage (Geotab), and DVIR completion.
  • Lead safety initiatives across the fleet through driver coaching, incident prevention, policy enforcement, and corrective action programs.
  • Partner with Dispatch Supervisors to ensure drivers follow documented safety procedures and equipment protocols.
  • Manage vendor relationships for maintenance, rentals, and fleet services.
  • Monitor asset performance and lifecycle to optimize cost, uptime, and safety.
  • Track and report on fleet metrics, delivery performance, and cost controls.
• Financial Oversight & P&L Ownership
  • Own the fleet and delivery P&L, including budgeting, forecasting, and cost control across all related expenses.
  • Lead annual budget planning and collaborate cross-functionally to align delivery performance with sales targets and operational capacity.
  • Monitor performance against budget and delivery KPIs, and develop and execute strategies to improve delivery profitability while maintaining service standards.
• Delivery Process Oversight
  • Provide strategic oversight of the end-to-end delivery process, ensuring the right people, systems, and resources are in place to execute effectively.
  • Align cross-functional teams around the Delivery Excellence framework—from order creation to billing.
  • Ensure Dispatch Supervisors manage routing, scheduling, and real-time tracking using Dispatch Track.
  • Monitor performance metrics and drive continuous improvement in delivery accuracy, timeliness, and customer satisfaction.
• Team Leadership & Supervision
  • Lead and develop Dispatch Supervisors, ensuring effective coaching and management of driver teams, actively engaging in performance discussions, and supporting retention and succession planning.
  • Ensure drivers consistently meet company standards for safety, order validation, equipment use, and customer interaction.
  • Actively lead in driver staffing decisions, including interviewing, selection, and onboarding processes.
  • Promote a culture of accountability, safety, and service excellence across the team.
  • Collaborate closely with Area and Branch Leadership Teams to align delivery operations with business objectives and ensure exceptional customer outcomes.

Up to 60% travel within the assigned area (Maryland and Virginia).

$85,000-$100,000 annual, plus bonus opportunities.

• 5+ years of experience in fleet, logistics, or delivery operations, preferably in a multi-site or centralized model.
• Proven leadership experience managing teams of dispatchers and drivers.
• Strong knowledge of DOT compliance, telematics systems (Geotab), and delivery platforms (Dispatch Track).
• Experience with asset lifecycle management, vendor relations, and cost optimization.
• Excellent communication, problem-solving, and cross-functional collaboration skills.
• Demonstrated experience managing a departmental or operational P&L.
• Bachelor's degree in Logistics, Transportation, Business, or related field preferred.

• Strategic thinker with hands‑on operational experience.
• Data‑driven decision maker with a focus on safety, efficiency and customer experience.
• Comfortable leading change and scaling processes across multiple locations.

• Competitive Compensation
• Medical, Dental and Vision plans
• Paid Time…