Jobs › Reworld

Head of Transportation (Waste and Environmental Services)

Reworld · Works From Home, IL · $160,684–$239,151 a year · Full time

Posted Aug 26, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a time you improved safety results across a large fleet. What did you change?

What they are checking: Whether they have driven real safety change in collection or hauling operations.

Tell me about a time you had to standardize practices across sites that each did things their own way.

What they are checking: Whether they can drive consistency without losing local buy-in.

How do you lead a team when you work from home and most of the fleet is in the field?

What they are checking: Whether they can lead remotely and still know what's happening on the ground.

What would you do

You're stepping into a brand-new role. What would you do in your first 90 days to understand our fleet?

What they are checking: Whether they can build a function from scratch and find the biggest gaps quickly.

You report to the EVP of Operations. How would you make the case for a big capital spend on new trucks?

What they are checking: Whether they can build a business case leadership will trust.

Driver turnover is high. What would you do about it?

What they are checking: Whether they see recruiting and retention as part of the transportation job.

How would you work with procurement on truck purchases and maintenance contracts?

What they are checking: Whether they partner well on big vendor decisions.

About the work

How do you decide when to repair, rebuild or replace a truck or piece of mobile equipment?

What they are checking: Whether they think in total cost of ownership, which drives fleet spending decisions.

What metrics would you use to run a fleet of trucks, mobile equipment and rolling stock?

What they are checking: Whether they know metrics like uptime, cost per mile, PM compliance and accident rates.

How do you keep a growing fleet compliant with DOT rules across many sites?

What they are checking: Whether they can build systems for driver files, inspections and hours of service at scale.

How do you think about alternative fuel or electric trucks for a sustainability-focused waste company?

What they are checking: Whether they can weigh sustainability goals against cost and reliability realistically.

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The full job description

As published by Reworld.

Who we are For more than 40 years, Reworld has been a leader in sustainable waste solutions, providing our customers with innovative solutions that help them achieve carbon-negative outcomes. Our Vision Reworld is leading the charge to a carbon-negative future through revolutionary sustainable materials management solutions that reduce, reuse, recycle and reimagine waste for the benefit of society and the environment. Our Business Reworld partners with businesses by offering cutting-edge engineering and innovative solutions, to help customers reduce, reuse, recycle and recover value from waste streams and meet or exceed their sustainability goals. Our Value Reworld's differentiator comes from our ecosystem of technology, facilities and partnerships, trusted by the world’s largest organizations to reimagine waste management for a smarter, more sustainable world. All that we’re missing is you. Apply today! About the role About the Company and Role 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 productivity (e.g., backhauling opportunities). • Collaborate cross-functionally with operations, sustainability, and customer service teams to align transportation strategy with broader company environmental targets, such as reducing fleet carbon footprint and improving fuel economy. Qualifications Candidates should bring a minimum of 10 years of experience in transportation, logistics, or fleet management, with at least 5 years in a leadership role, ideally within waste management, recycling, or a related logistics-heavy industry. A bachelor's degree in logistics, supply chain management, business administration, or a related field is preferred; an MBA is a plus. Strong working knowledge of DOT/FMCSA regulations, fleet maintenance best practices, and emerging clean transportation technologies is essential. The ideal candidate will have a demonstrated history of improving fleet efficiency, reducing emissions, and managing large, multi-site teams. Experience with fleet management software, telematics, and route optimization tools is highly valued, as is strong financial acumen for budgeting and P&L management. Work Location : While the desired location is our HQ in Florham Park, NJ, remote or hybrid work from other locations is possible. Locations close to our regional hubs are highly preferred. All Reworld positions require a candidate's ability to perform the duties and responsibilities of the role while upholding Reworld's Values, including (but not limited to) contributing to a safe and inclusive workplace, delivering results through trust, and building breakthrough capabilities. Please note that Level, Title and/or Salary may be adjusted based on the applicant's experience or skills. Pay Transparency Reworld is committed to paying its staff equitably, and we strive to provide competitive compensation and benefits packages. The range below reflects Reworld’s reasonable estimate of base pay for this role based on primary posting location. It is expected that most qualified candidates in this location will fall within the posting range. The final salary offered for this role will be determined based on factors including, but not limited to: experience, education, geographic location, skills and competencies, travel requirements and/or union contracts (if applicable). Pay ranges are reviewed from time to time and may be modified in the future. The pay range for the primary location of this position is: $160,684.00 - $239,151.00 USD Reworld™ provides an industry-leading benefits package that supports the whole person—and their families—through a balanced approach to mental, physical, and financial wellbeing. Regular full-time employees based in the USA have access to comprehensive medical, prescription drugs, dental, and vision coverage, FSA, HSA, short- and long-term disability benefits. Our 401(k) plan is industry-leading, with an up to 7% company match. Additional benefits include Company-paid life and AD&D insurance, EAP, paid parental leave, and educational assistance. For more information regarding these offerings, please visit the Reworld Careers Benefits Page . Reworld™ reserves the right to amend, suspend or terminate any benefit plan, in whole or in part, at any time. Our DEI Commitment Reworld is an Equal Opportunity Employer, has developed an Affirmative Action Program (AAP), and will not discriminate against any qualified applicants because of race, color, religion, sex, national origin, sexual orientation, gender identity, disability (including perceived disability, physical, mental, and/or intellectual disabilities), veteran status, liability for service in the Armed Forces of the United States, or any other characteristic protected by law. Know Your Rights ( Click to view poster ) If you are an individual with a disability or a disabled veteran, you may request a reasonable accommodation if you are unable or limited in your ability to access job openings or apply for a job on this site because of your disability. You can request reasonable accommodations by going to Reworldwaste.com and clicking on the ‘Contact Us’ button. Under Inquires, select ‘Careers’ in the Interest field, fill out all required fields including your message. In the message section, please note this is a ‘Job Application Accommodation Request’. Attention Staffing Agencies & Search Firms Reworld may sometimes selectively collaborate with staffing agencies and search firms (Agencies). Reworld will only consider candidates from Agencies with whom a signed agreement and a duly authorized work order (for a specific role) has been duly executed. Any unsolicited candidate submissions or candidate submissions from Agencies that do not meet these criteria, will be deemed invalid and ineligible for any fees.

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