Head of Transportation; Waste and Environmental Services

Head Of Transportation

Our company is a sustainability-driven waste management organization committed to reducing landfill dependency, advancing the circular economy, and delivering best-in-class collection and hauling services.

To support our fast-growing fleet of trucks, mobile equipment, and rolling stock, we are creating a new role for the Head of Transportation.

Reporting to the EVP, Operations, this leadership role is responsible for the strategic direction and execution, governance, and continuous improvement of our transportation assets, network, logistics, and operations.

The Head of Transportation will lead Reworld's enterprise fleet strategy, driving productivity, standardization, and governance across all regions — spanning both strategy establishment and strategy execution.

We are looking for a hands-on leader who is passionate about sustainability and operational excellence, comfortable balancing the practical demands of running a large fleet with a long-term vision for cleaner, smarter transportation. Effective communication and stakeholder management skills are essential, as this role interfaces with executive leadership, municipal partners, regulators, and frontline employees.

Key Responsibilities

You will also drive an enterprise fleet reliability program and deploy a transportation management system enabling route optimization and dispatch operations across multiple service territories to maximize efficiency, minimize fuel consumption, and reduce overall emissions.

As a Corporate COE, you will partner closely with regional transportation teams, fostering a culture of safety, accountability, and continuous improvement. You will ensure full compliance with DOT, FMCSA, OSHA, and state/local environmental regulations, and will partner with EHS teams to maintain rigorous safety standards and reduce incident rates.

Key duties include:

• Fleet Reliability Program — Develop and execute an enterprise Fleet Reliability Program and deploy a Transportation Management System focused on:
• Maximizing fleet uptime
• Reducing lifecycle costs
• Improving asset utilization
• Leveraging predictive maintenance analytics
• Standardizing maintenance practices across the organization
• Driving continuous improvement through performance metrics and data-driven decision-making
• DOT Compliance & Safety Ownership
• Own DOT and FMCSA compliance across the enterprise fleet, including driver qualification, hours-of-service, vehicle inspection, and recordkeeping requirements.
• Own transportation safety performance, partnering with EHS teams to set standards, reduce incident rates, and drive accountability across regions.
• Partnership with Procurement on Fleet Acquisition and 3PL Strategy
• Partner with Procurement on sourcing and contracting for fleet assets, including third-party maintenance services.
• Collaborate on strategic supplier partnerships and 3PL sourcing initiatives that reduce total cost of ownership while improving service quality and reliability.
• Capital Planning & Fleet Replacement Strategy
• Lead long-term fleet replacement strategy and capital planning.
• Balance operational requirements, capital investment, maintenance costs, and residual value to optimize total cost of ownership.
• Budgeting and forecasting for the transportation division, identifying cost-saving opportunities without compromising service quality or sustainability goals.
• Evaluating and implementing fleet telematics, GPS tracking, and route optimization software; negotiating contracts with vendors, fuel suppliers, and equipment manufacturers
• Representing the company in regulatory matters, municipal contract negotiations, and industry sustainability initiatives.
• Regional Partnership and Cross-Fleet Productivity Ownership
• Partner closely with regional transportation leaders, equipping and enabling them to execute against the enterprise strategy, including vehicle acquisition, maintenance programs, and the transition toward low-emission and alternative-fuel vehicles (CNG, electric, or hybrid).
• Enterprise productivity budget ownership.
• In-house vs. external hauler optimization.
• Asset and driver utilization/productivity improvement.
• Enterprise transportation network strategy and…