Transportation Manager

Location: Fillmore Linen Service — Chicago, IL (North Lawndale)

Reports To: General Manager

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About Fillmore Linen

We're on a mission beyond linen—we're reinvesting in Chicago's North Lawndale community through purpose-driven work that services the linen needs of Chicago hospitals and provides real opportunity. With more than 9 million pounds of linen processed annually and a 32 million-pound capacity facility opening in 2026, we're growing fast—and we're committed to growing our people alongside our operations.

The Opportunity

The Transportation Manager will lead Fillmore's delivery operations—managing our driver team, optimizing route efficiency, overseeing fleet performance, and ensuring flawless execution of the critical final mile that connects our plant operations to patient care. You'll build and lead a high-performing transportation team, scale logistics for significant growth through 2026 and beyond, and manage the full scope of delivery operations including costs, safety, compliance, and customer satisfaction. This is a hands-on leadership role requiring both strategic thinking and operational excellence—someone who can coach drivers through challenges, optimize complex multi-state routes, and build the transportation infrastructure that supports our expanding reach.

Key Responsibilities

Driver Team Leadership & Development

  • Lead, manage, and develop a team of 7+ delivery drivers (expanding significantly with 2026 facility growth) on professional conduct, customer service excellence, safety protocols, and operational best practices.

  • Coach and mentor drivers, proactively address conflicts, build morale, and foster a positive team culture.

  • Conduct ride-alongs with drivers to assess performance, provide real-time coaching, ensure route adherence, and maintain customer service standards.

  • Manage performance issues decisively and fairly—addressing attendance, attitude, safety violations, and service quality concerns promptly.

Route Optimization & Operations Management

  • Design, analyze, optimize, and implement delivery route improvements to maximize efficiency, profitability, and service quality.

  • Manage current 7-route network and plan for significant route expansion across Chicago, Indiana, and expanding Wisconsin territories to support 2026 business growth and new customer acquisition.

  • Be available 24/7 for driver emergencies, route issues, and operational challenges, stepping in as may be needed to cover unplanned absences; serve as the escalation point for urgent situations.

  • Balance competing priorities: delivery time windows, fuel efficiency, labor costs, customer satisfaction, and driver workload.

  • Coordinate delivery schedules with plant operations to ensure seamless handoffs between production and transportation.

  • Leverage technology such as ControlTex Transportation Management System (TMS) to improve route planning, tracking, and performance visibility.

Fleet Management & Maintenance

  • Oversee fleet of 5+ trucks (growing with 2026 expansion) and manage preventative maintenance to extend vehicle lifecycles, ensure optimal performance, and maintain readiness for daily operations.

  • Evaluate and select appropriate vehicles for healthcare linen delivery—considering payload capacity, maneuverability, fuel efficiency, and operational requirements.

  • Manage truck leasing decisions, lease renewals, and purchase vs. lease analysis to optimize fleet costs and capabilities.

  • Build and maintain relationships with maintenance vendors, leasing companies, and service providers; negotiate favorable terms and ensure quality service.

  • Ensure all vehicles meet safety standards, pass inspections, and comply with DOT/FMCSA regulations.

Cost Management & Budget Control

  • Manage and optimize transportation budget of driver wages, overtime, truck leases, fuel, maintenance, insurance, and operational expenses, without compromising service quality or safety standards. Prepare budget forecasts for transportation expansion, capital equipment needs, and operational scaling.

  • Control overtime costs through effective scheduling, route optimization, and proactive staffing management.

  • Track and analyze key performance metrics: cost per delivery, miles per gallon, maintenance costs per vehicle, on-time delivery rates, and labor efficiency.

  • Balance cost efficiency with service excellence—finding the optimal intersection of profitability and customer satisfaction.

Safety, Compliance & Risk Management

  • Ensure all drivers operate safely and comply with DOT/FMCSA regulations, company policies, and industry best practices.

  • Control the management of driver qualification files, training records, hours of service compliance, and required documentation.

  • Investigate accidents, incidents, and near-misses; implement corrective actions and preventative measures.

  • Conduct regular safety meetings and training sessions on defensive driving, vehicle inspections, and hazard awareness.

  • Manage insurance claims, coordinate with risk management, and work to reduce insurance costs through strong safety performance.

  • Ensure compliance with healthcare-specific delivery requirements including infection control protocols and proper linen handling during transport.

Customer Interface & Service Quality

  • Serve as escalation point for customer delivery issues, service complaints, and special requests—resolving problems quickly and professionally.

  • Partner with Customer Service Representatives to coordinate delivery schedules, accommodate special requests, and ensure customer satisfaction.

  • Ensure drivers represent Fillmore professionally at customer sites—maintaining appearance standards, communication protocols, and service excellence.

  • Conduct periodic customer site visits to assess delivery performance, gather feedback, and strengthen relationships.

  • Track on-time delivery performance and work cross-functionally to meet or exceed customer service level agreements.

Operations Coordination & Systems Management

  • Coordinate closely with plant operations, production, and logistics teams to ensure seamless material flow from plant to customer.

  • Communicate delivery challenges and capacity constraints to enable proactive communication with our customers.

  • Lead ControlTex Transportation Management System implementation and optimization—training drivers, establishing workflows, and leveraging data for continuous improvement.

  • Utilize technology for route tracking, driver communication, delivery confirmation, and performance analytics.

  • Provide operational feedback to leadership on transportation challenges, improvement opportunities, and strategic recommendations.

What We're Looking For

  • Experience: 5-7 years in transportation management, logistics operations, or fleet management—preferably in delivery-intensive environments such as distribution, manufacturing, or service operations.

  • Leadership: Proven ability to lead, motivate, and manage driver teams in high-energy environments; strong conflict resolution and team-building skills essential.

  • Operational Excellence: Track record optimizing routes, controlling costs, and improving transportation efficiency and service quality.

  • Strategic Operator: Equally comfortable leading from the front line and covering routes when needed; ability to think quickly, make sound decisions under pressure, and resolve complex operational challenges. CDL preferred but not required.

  • Fleet Management: Experience managing vehicle maintenance, vendor relationships, and fleet optimization; ability to evaluate and select appropriate equipment.

  • Cost Management: Strong financial acumen with experience managing transportation budgets, controlling expenses, and tracking performance metrics.

  • Logistics Proficiency: Familiarity with Chicago, Indiana, and Wisconsin delivery routes, and comfortable with transportation management systems and route optimization software; ControlTex experience strongly preferred. 

  • Safety & Compliance: Knowledge of DOT/FMCSA regulations and transportation safety standards; commitment to regulatory compliance and risk management.

  • 24/7 Availability: Willing to be on-call for driver emergencies, route issues, and operational challenges; flexible schedule to support round-the-clock operations.

  • Mission Alignment: Commitment to Fillmore's values of community reinvestment, employee development, and purpose-driven work.

Bonus: Healthcare laundry industry experience, HLAC familiarity, or background in healthcare logistics and delivery operations.

Why Join Fillmore?

  • Leadership impact: build and develop a high-performing transportation team during significant organizational growth.

  • Strategic role: shape transportation infrastructure for our 2026 facility expansion and long-term scaling.

  • Operational ownership: full accountability for routes, fleet, costs, and delivery excellence—real authority to drive results.

  • Mission-driven work: lead a team that's part of something bigger than logistics—community opportunity and healthcare excellence.

Competitive compensation, benefits, and professional development opportunities.

Apply Today

If you're a transportation leader who can build high-performing teams, optimize complex operations, and scale delivery infrastructure for growth—and who brings both operational rigor and people skills to your work—we want to meet you. Join us in building a transportation operation where operational excellence and community impact drive forward together.

Apply Here