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Transportation Manager

Sysco · Woodridge, IL · $80,000–$90,000 a year · Full time

Posted Aug 5, 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 your experience working in a union environment.

What they are checking: Whether they can manage within a contract and keep a working relationship with union representatives.

Tell me about a time you improved on-time delivery for a team you managed.

What they are checking: Whether they have actually moved delivery performance and can explain how.

What would you do

A driver repeatedly shows up in reports for hard braking and speeding. How do you handle it?

What they are checking: Whether they address safety issues promptly and fairly, with coaching and follow-through.

A truck breaks down midway through a route full of customer deliveries. What do you do?

What they are checking: Whether they can recover service fast and keep customers informed.

How do you decide when a vehicle should come out of service for maintenance?

What they are checking: Whether they put safety and preventive maintenance ahead of short-term schedule pressure.

About the work

Walk me through how you plan routes for a day's deliveries.

What they are checking: Whether they use routing platforms well and balance cost, timing and driver hours.

What DOT regulations matter most in your daily work, and how do you make sure drivers follow them?

What they are checking: Whether they know hours of service, inspections and driver qualification rules and enforce them.

How do you use telematics and other technology to monitor driver performance?

What they are checking: Whether they use data to coach drivers on safety and efficiency rather than to punish.

How do you keep transportation expenses under control as volumes and fuel prices change?

What they are checking: Whether they manage cost per stop or per mile actively, as the posting emphasizes.

How do you keep accurate records of driver pay and equipment maintenance?

What they are checking: Whether they keep reliable records, since errors affect pay and safety compliance.

Practice this interview out loud.

Offer builds a real interview for this exact role at Sysco from your resume and this job description, asks the questions one at a time, and tells you what landed. The first one is free.

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The full job description

As published by Sysco.

Company: US0670 Edward Don Sales Territory: None Zip Code: 60517 Travel Percentage: 0 Compensation Range: $80,000 - $90,000 The compensation range provided is in compliance with state specific laws. Factors that may be used to determine your actual rate of pay include your specific skills, years of experience and other factors. You may be eligible to participate in the Company's Incentive Plan. BENEFITS INFORMATION: For information on Sysco’s Benefits, please visit https://SyscoBenefits.com QUALIFICATIONS Education • A high school diploma/GED Experience • 4 - 8 years of transportation experience within a management level • Strong computer experience and routing platforms • Department of Transportation (DOT) regulations • Knowledge of union experience preferred JOB SUMMARY Responsible for the safe, efficient, and timely delivery of the product to our customers, accomplished through thorough planning and an on-going process of monitoring driver performance, equipment condition, and business volume while effectively managing expenses in an ever-changing environment. RESPONSIBILITIES • Closely monitor driver performance via the use of available technology and other control features • Maintain detailed records of driver pay, equipment maintenance, and equipment performance • Review driver logs and paperwork to ensure accuracy and adherence to policy and Department of Transportation (DOT) regulations • Closely monitor equipment to ensure safe operation and minimize breakdown • Order necessary parts and equipment used in driver performance of responsibilities • Review routing and make the necessary adjustments to ensure optimal efficiency • Hire, train, direct and discipline transportation personnel to achieve the most effective use of human and physical assets • Plan and schedule the assignment of work for transportation personnel • Process bi-weekly payroll • Verify vendor invoices and complete A/P vouchers • Monitor trip records and fuel reports for mileage, fuel costs, and fuel economy • Monitor monthly expenses in relation to planning and make the necessary changes • Perform the necessary requirements of the Department of Transportation • Assure safety awareness and compliance practices are adhered to in the department and distribution center • Direct and coordinate all driver observations relative to safe operations, the performance of PWM and accurate delivery procedures. • Other duties as assigned by Management Physical Demands • Work is primarily sedentary in nature • Frequent standing and bending is required when checking equipment • A substantial portion of the day is spent on key entry • You must have the ability to communicate clearly, primarily via telephone, with vendors, shippers, customers, and company personnel. License or Certifications None, however a CDL driver's license and certificate of Department of Transportation (DOT) regulations training is preferred. Important Notice for CDL Holders: If you hold a valid Class A or B Commercial Driver’s License (CDL), you will be designated as a CDL driver for Sysco, regardless of the specific position for which you are applying. As a result, this classification may affect your job responsibilities and will subject you to compliance requirements under Department of Transportation (DOT) regulations — including participation in the DOT Drug and Alcohol Random Testing Program. Candidates must have: • Be 21 years or older • No drug or alcohol violations within the past 3 years • No open violations listed in the FMCSA Drug and Alcohol Clearinghouse OVERVIEW: Sysco is the global leader in foodservice distribution. With over 71,000 colleagues and a fleet of over 13,000 vehicles, Sysco operates approximately 333 distribution facilities worldwide and serves more than 700,000 customer locations. We offer our colleagues the opportunity to grow personally and professionally, to contribute to the success of a dynamic organization, and to serve others in a manner that exceeds their expectations. We’re looking for talented, hard-working individuals to join our team. Come grow with us and let us show you why Sysco is at the heart of food and service. AFFIRMATIVE ACTION STATEMENT: Applicants must be currently authorized to work in the United States. We are proud to be an Equal Opportunity and Affirmative Action employer, and consider qualified applicants without regard to race, color, creed, religion, ancestry, national origin, sex, sexual orientation, gender identity, age, disability, veteran status or any other protected factor under federal, state or local law. This opportunity is available through Sysco Corporation, its subsidiaries and affiliates.

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