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Transportation Supervisor Careers at Sysco - Chicago, Illinois | Apply Now!

Sysco

Transportation Supervisor Careers at Sysco - Chicago, Illinois | Apply Now!

full-timePosted: Feb 17, 2026

Job Description

Transportation Supervisor at Sysco Chicago: A Comprehensive Overview

Role Overview

As a Transportation Supervisor at Sysco Chicago, you will play a crucial role in ensuring the efficient and safe delivery of products to our customers. This leadership position involves overseeing a team of Delivery Associates, managing daily operations, and maintaining compliance with all relevant regulations. Your responsibilities will extend to various aspects of delivery management, including route optimization, driver safety, customer service, and cost control. You will be a key contributor to Sysco's commitment to providing exceptional service and maintaining a reliable supply chain.

A Day in the Life of a Transportation Supervisor

Your day will be dynamic and multifaceted, requiring a blend of leadership, problem-solving, and communication skills. Here's a glimpse into what a typical day might entail:

  • Morning Briefing: Start the day by conducting a pre-shift meeting with your team of Delivery Associates. Review delivery schedules, address any potential issues, and reinforce safety protocols.
  • Route Optimization: Analyze delivery routes to identify opportunities for efficiency improvements. Consider factors such as traffic patterns, delivery windows, and customer locations.
  • Driver Supervision: Monitor the performance of Delivery Associates throughout the day. Ensure they adhere to planned routes, follow safety procedures, and provide excellent customer service.
  • Regulatory Compliance: Verify that all drivers are compliant with DOT and OSHA regulations. Review electronic logs for accuracy and completeness.
  • Customer Interaction: Communicate with Sales Management and Marketing Associates to resolve any customer issues or delivery challenges. Visit customer locations as needed to assess delivery difficulties and build relationships.
  • Problem Solving: Address any unexpected issues that arise during the day, such as vehicle breakdowns, traffic delays, or delivery discrepancies.
  • Performance Management: Provide coaching and feedback to Delivery Associates to improve their performance. Conduct performance reviews and address any disciplinary issues.
  • Safety Oversight: Work closely with the Safety department to conduct safety inspections, investigate accidents, and implement safety training programs.
  • Administrative Tasks: Complete various administrative tasks, such as preparing work schedules, managing labor hours, and ordering supplies.

Why Chicago, Illinois?

Chicago is a major transportation hub with a robust logistics infrastructure, making it an ideal location for Sysco's operations. The city offers a diverse talent pool, excellent transportation networks, and access to a large customer base. Chicago's vibrant economy and cultural attractions also make it an attractive place to live and work.

Career Path

The Transportation Supervisor role can serve as a stepping stone to various career advancement opportunities within Sysco. With demonstrated success and leadership skills, you may be promoted to positions such as:

  • Transportation Manager: Oversee a larger team of Transportation Supervisors and manage a broader range of delivery operations.
  • Logistics Manager: Manage the overall flow of goods within the supply chain, including transportation, warehousing, and inventory management.
  • Operations Manager: Oversee all aspects of the distribution center's operations, including transportation, warehousing, and customer service.
  • Senior Leadership Roles: Advance to senior leadership positions within the organization, such as Director of Operations or Vice President of Supply Chain.

Salary and Benefits

The estimated annual salary range for a Transportation Supervisor at Sysco Chicago is $78,000 to $117,000. The actual salary may vary based on experience, skills, and qualifications.

Sysco offers a comprehensive benefits package that includes:

  • Health Insurance: Medical, dental, and vision coverage.
  • Paid Time Off: Vacation, sick leave, and holidays.
  • Retirement Plan: 401(k) with company match.
  • Employee Stock Purchase Plan: Opportunity to purchase Sysco stock at a discounted price.
  • Life Insurance: Coverage for employees and their dependents.
  • Disability Insurance: Short-term and long-term disability coverage.
  • Flexible Spending Accounts: Pre-tax savings accounts for healthcare and dependent care expenses.
  • Wellness Programs: Resources and programs to support employee health and well-being.
  • Employee Assistance Program: Confidential counseling and support services.
  • Tuition Reimbursement: Financial assistance for eligible educational expenses.

Sysco Culture

Sysco is committed to creating a positive and inclusive work environment where employees can thrive. The company values teamwork, integrity, and customer service. Sysco also emphasizes employee development and provides opportunities for growth and advancement.

How to Apply

Interested candidates can apply for the Transportation Supervisor position through the Sysco careers website. Please submit your resume and cover letter, highlighting your relevant experience and qualifications.

Frequently Asked Questions (FAQ)

  1. What are the key responsibilities of a Transportation Supervisor?

    The key responsibilities include supervising Delivery Associates, ensuring regulatory compliance, managing labor hours, and providing excellent customer service.

  2. What qualifications are required for this role?

    A high school diploma or GED is required, and a bachelor's degree in Business Management or a related field is preferred. 1-3 years of related experience is also necessary.

  3. What is the salary range for a Transportation Supervisor at Sysco Chicago?

    The estimated annual salary range is $78,000 to $117,000, depending on experience and qualifications.

  4. What benefits does Sysco offer?

    Sysco offers a comprehensive benefits package, including health insurance, paid time off, retirement plan, and employee stock purchase plan.

  5. What is the career path for a Transportation Supervisor?

    The Transportation Supervisor role can lead to advancement opportunities such as Transportation Manager, Logistics Manager, or Operations Manager.

  6. What is the work environment like at Sysco?

    Sysco is committed to creating a positive and inclusive work environment where employees can thrive.

  7. How does Sysco support employee development?

    Sysco provides opportunities for growth and advancement through training programs and career development initiatives.

  8. What is Sysco's commitment to safety?

    Sysco prioritizes safety and provides ongoing training and resources to ensure a safe working environment.

  9. What are the opportunities for advancement?

    Advancement opportunities include Transportation Manager, Logistics Manager, Operations Manager, and leadership roles.

  10. What is the interview process like?

    The interview process may include phone screenings, in-person interviews, and assessments to evaluate your skills and qualifications.

Locations

  • Chicago, Illinois, United States

Salary

Estimated Salary Rangemedium confidence

85,800 - 128,700 USD / yearly

Source: ai estimated

* This is an estimated range based on market data and may vary based on experience and qualifications.

Skills Required

  • Supervisory skillsintermediate
  • Delivery operations managementintermediate
  • DOT complianceintermediate
  • OSHA complianceintermediate
  • Labor managementintermediate
  • Budget managementintermediate
  • Fleet managementintermediate
  • Customer serviceintermediate
  • Communication skillsintermediate
  • Problem-solvingintermediate
  • Conflict resolutionintermediate
  • Training and developmentintermediate
  • Performance managementintermediate
  • Safety managementintermediate
  • Regulatory complianceintermediate

Required Qualifications

  • High school diploma or GED (experience)
  • Bachelor's degree in Business Management, Supply Chain Management or related field preferred (experience)
  • 1-3 years of related experience in transportation or logistics (experience)
  • Knowledge of DOT and OSHA regulations (experience)
  • Experience with electronic logging devices (ELDs) (experience)
  • Strong leadership and communication skills (experience)
  • Ability to manage and motivate a team (experience)
  • Proficiency in Microsoft Office Suite (experience)
  • Valid driver's license (experience)
  • Completion of a Sysco-approved defensive driving program (experience)
  • HazMat certification preferred (experience)
  • Ability to interpret and enforce company policies and procedures (experience)

Responsibilities

  • Supervise daily work and safety of Delivery Associates
  • Ensure adherence to standard operating procedures
  • Ensure adherence to planned routes
  • Provide safe and efficient customer service
  • Ensure compliance with local, state, and federal regulations (DOT, OSHA, etc.)
  • Ensure accurate maintenance of electronic logs
  • Manage labor hours and consumable supplies within budget
  • Prepare work schedules
  • Oversee the proper selection and utilization of company assets
  • Organize required repairs with proper departments
  • Review delivery functions and productivity reporting
  • Suggest efficiency ideas and cost reduction measures
  • Assist with implementation of delivery changes
  • Interpret and enforce Company policies, protocols and procedures
  • Communicate with Sales Management and Marketing Associates to resolve customer issues
  • Visit customer locations to address issues and assess delivery difficulty
  • Preserve associate relations through regular department meetings
  • Maintain on-going interaction with associates
  • Keep open communication channels with associates
  • Monitor associate morale
  • Submit and respond to ideas to improve associate engagement
  • Coordinate efforts with the Safety department for training and accident investigations
  • Make recommendations for disciplinary action
  • Execute management functions of staff selection, development, and performance reviews
  • Perform duties of supervised associates as needed

Benefits

  • general: Competitive salary
  • general: Comprehensive health insurance (medical, dental, vision)
  • general: Paid time off (vacation, sick, holidays)
  • general: 401(k) retirement plan with company match
  • general: Employee stock purchase plan
  • general: Life insurance
  • general: Disability insurance
  • general: Flexible spending accounts (FSAs)
  • general: Health savings accounts (HSAs)
  • general: Wellness programs
  • general: Employee assistance program (EAP)
  • general: Tuition reimbursement
  • general: Career development opportunities
  • general: Employee discounts on Sysco products
  • general: Incentive Plan Eligibility
  • general: Relocation assistance (if applicable)

Target Your Resume for "Transportation Supervisor Careers at Sysco - Chicago, Illinois | Apply Now!" , Sysco

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Tags & Categories

TransportationLogisticsManagementSupervisorySupply ChainDistributionCustomer ServiceSafetyComplianceChicagoIllinoisTransportation SupervisorDelivery SupervisorLogistics SupervisorFleet ManagementDOT ComplianceOSHA ComplianceWarehouseTransportation ManagementDelivery OperationsRoute OptimizationDriver ManagementSysco CareersSysco ChicagoChicago JobsIllinois JobsLogistics Jobs ChicagoTransportation Jobs ChicagoManagement JobsSupervisory RolesFleet SupervisorDistribution SupervisorSysco BenefitsDelivery AssociateChicago LogisticsTransportation IndustrySupply Chain ManagementFood ServiceSupply ChainSalesLogistics

Answer 10 quick questions to check your fit for Transportation Supervisor Careers at Sysco - Chicago, Illinois | Apply Now! @ Sysco.

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Sysco logo

Transportation Supervisor Careers at Sysco - Chicago, Illinois | Apply Now!

Sysco

Transportation Supervisor Careers at Sysco - Chicago, Illinois | Apply Now!

full-timePosted: Feb 17, 2026

Job Description

Transportation Supervisor at Sysco Chicago: A Comprehensive Overview

Role Overview

As a Transportation Supervisor at Sysco Chicago, you will play a crucial role in ensuring the efficient and safe delivery of products to our customers. This leadership position involves overseeing a team of Delivery Associates, managing daily operations, and maintaining compliance with all relevant regulations. Your responsibilities will extend to various aspects of delivery management, including route optimization, driver safety, customer service, and cost control. You will be a key contributor to Sysco's commitment to providing exceptional service and maintaining a reliable supply chain.

A Day in the Life of a Transportation Supervisor

Your day will be dynamic and multifaceted, requiring a blend of leadership, problem-solving, and communication skills. Here's a glimpse into what a typical day might entail:

  • Morning Briefing: Start the day by conducting a pre-shift meeting with your team of Delivery Associates. Review delivery schedules, address any potential issues, and reinforce safety protocols.
  • Route Optimization: Analyze delivery routes to identify opportunities for efficiency improvements. Consider factors such as traffic patterns, delivery windows, and customer locations.
  • Driver Supervision: Monitor the performance of Delivery Associates throughout the day. Ensure they adhere to planned routes, follow safety procedures, and provide excellent customer service.
  • Regulatory Compliance: Verify that all drivers are compliant with DOT and OSHA regulations. Review electronic logs for accuracy and completeness.
  • Customer Interaction: Communicate with Sales Management and Marketing Associates to resolve any customer issues or delivery challenges. Visit customer locations as needed to assess delivery difficulties and build relationships.
  • Problem Solving: Address any unexpected issues that arise during the day, such as vehicle breakdowns, traffic delays, or delivery discrepancies.
  • Performance Management: Provide coaching and feedback to Delivery Associates to improve their performance. Conduct performance reviews and address any disciplinary issues.
  • Safety Oversight: Work closely with the Safety department to conduct safety inspections, investigate accidents, and implement safety training programs.
  • Administrative Tasks: Complete various administrative tasks, such as preparing work schedules, managing labor hours, and ordering supplies.

Why Chicago, Illinois?

Chicago is a major transportation hub with a robust logistics infrastructure, making it an ideal location for Sysco's operations. The city offers a diverse talent pool, excellent transportation networks, and access to a large customer base. Chicago's vibrant economy and cultural attractions also make it an attractive place to live and work.

Career Path

The Transportation Supervisor role can serve as a stepping stone to various career advancement opportunities within Sysco. With demonstrated success and leadership skills, you may be promoted to positions such as:

  • Transportation Manager: Oversee a larger team of Transportation Supervisors and manage a broader range of delivery operations.
  • Logistics Manager: Manage the overall flow of goods within the supply chain, including transportation, warehousing, and inventory management.
  • Operations Manager: Oversee all aspects of the distribution center's operations, including transportation, warehousing, and customer service.
  • Senior Leadership Roles: Advance to senior leadership positions within the organization, such as Director of Operations or Vice President of Supply Chain.

Salary and Benefits

The estimated annual salary range for a Transportation Supervisor at Sysco Chicago is $78,000 to $117,000. The actual salary may vary based on experience, skills, and qualifications.

Sysco offers a comprehensive benefits package that includes:

  • Health Insurance: Medical, dental, and vision coverage.
  • Paid Time Off: Vacation, sick leave, and holidays.
  • Retirement Plan: 401(k) with company match.
  • Employee Stock Purchase Plan: Opportunity to purchase Sysco stock at a discounted price.
  • Life Insurance: Coverage for employees and their dependents.
  • Disability Insurance: Short-term and long-term disability coverage.
  • Flexible Spending Accounts: Pre-tax savings accounts for healthcare and dependent care expenses.
  • Wellness Programs: Resources and programs to support employee health and well-being.
  • Employee Assistance Program: Confidential counseling and support services.
  • Tuition Reimbursement: Financial assistance for eligible educational expenses.

Sysco Culture

Sysco is committed to creating a positive and inclusive work environment where employees can thrive. The company values teamwork, integrity, and customer service. Sysco also emphasizes employee development and provides opportunities for growth and advancement.

How to Apply

Interested candidates can apply for the Transportation Supervisor position through the Sysco careers website. Please submit your resume and cover letter, highlighting your relevant experience and qualifications.

Frequently Asked Questions (FAQ)

  1. What are the key responsibilities of a Transportation Supervisor?

    The key responsibilities include supervising Delivery Associates, ensuring regulatory compliance, managing labor hours, and providing excellent customer service.

  2. What qualifications are required for this role?

    A high school diploma or GED is required, and a bachelor's degree in Business Management or a related field is preferred. 1-3 years of related experience is also necessary.

  3. What is the salary range for a Transportation Supervisor at Sysco Chicago?

    The estimated annual salary range is $78,000 to $117,000, depending on experience and qualifications.

  4. What benefits does Sysco offer?

    Sysco offers a comprehensive benefits package, including health insurance, paid time off, retirement plan, and employee stock purchase plan.

  5. What is the career path for a Transportation Supervisor?

    The Transportation Supervisor role can lead to advancement opportunities such as Transportation Manager, Logistics Manager, or Operations Manager.

  6. What is the work environment like at Sysco?

    Sysco is committed to creating a positive and inclusive work environment where employees can thrive.

  7. How does Sysco support employee development?

    Sysco provides opportunities for growth and advancement through training programs and career development initiatives.

  8. What is Sysco's commitment to safety?

    Sysco prioritizes safety and provides ongoing training and resources to ensure a safe working environment.

  9. What are the opportunities for advancement?

    Advancement opportunities include Transportation Manager, Logistics Manager, Operations Manager, and leadership roles.

  10. What is the interview process like?

    The interview process may include phone screenings, in-person interviews, and assessments to evaluate your skills and qualifications.

Locations

  • Chicago, Illinois, United States

Salary

Estimated Salary Rangemedium confidence

85,800 - 128,700 USD / yearly

Source: ai estimated

* This is an estimated range based on market data and may vary based on experience and qualifications.

Skills Required

  • Supervisory skillsintermediate
  • Delivery operations managementintermediate
  • DOT complianceintermediate
  • OSHA complianceintermediate
  • Labor managementintermediate
  • Budget managementintermediate
  • Fleet managementintermediate
  • Customer serviceintermediate
  • Communication skillsintermediate
  • Problem-solvingintermediate
  • Conflict resolutionintermediate
  • Training and developmentintermediate
  • Performance managementintermediate
  • Safety managementintermediate
  • Regulatory complianceintermediate

Required Qualifications

  • High school diploma or GED (experience)
  • Bachelor's degree in Business Management, Supply Chain Management or related field preferred (experience)
  • 1-3 years of related experience in transportation or logistics (experience)
  • Knowledge of DOT and OSHA regulations (experience)
  • Experience with electronic logging devices (ELDs) (experience)
  • Strong leadership and communication skills (experience)
  • Ability to manage and motivate a team (experience)
  • Proficiency in Microsoft Office Suite (experience)
  • Valid driver's license (experience)
  • Completion of a Sysco-approved defensive driving program (experience)
  • HazMat certification preferred (experience)
  • Ability to interpret and enforce company policies and procedures (experience)

Responsibilities

  • Supervise daily work and safety of Delivery Associates
  • Ensure adherence to standard operating procedures
  • Ensure adherence to planned routes
  • Provide safe and efficient customer service
  • Ensure compliance with local, state, and federal regulations (DOT, OSHA, etc.)
  • Ensure accurate maintenance of electronic logs
  • Manage labor hours and consumable supplies within budget
  • Prepare work schedules
  • Oversee the proper selection and utilization of company assets
  • Organize required repairs with proper departments
  • Review delivery functions and productivity reporting
  • Suggest efficiency ideas and cost reduction measures
  • Assist with implementation of delivery changes
  • Interpret and enforce Company policies, protocols and procedures
  • Communicate with Sales Management and Marketing Associates to resolve customer issues
  • Visit customer locations to address issues and assess delivery difficulty
  • Preserve associate relations through regular department meetings
  • Maintain on-going interaction with associates
  • Keep open communication channels with associates
  • Monitor associate morale
  • Submit and respond to ideas to improve associate engagement
  • Coordinate efforts with the Safety department for training and accident investigations
  • Make recommendations for disciplinary action
  • Execute management functions of staff selection, development, and performance reviews
  • Perform duties of supervised associates as needed

Benefits

  • general: Competitive salary
  • general: Comprehensive health insurance (medical, dental, vision)
  • general: Paid time off (vacation, sick, holidays)
  • general: 401(k) retirement plan with company match
  • general: Employee stock purchase plan
  • general: Life insurance
  • general: Disability insurance
  • general: Flexible spending accounts (FSAs)
  • general: Health savings accounts (HSAs)
  • general: Wellness programs
  • general: Employee assistance program (EAP)
  • general: Tuition reimbursement
  • general: Career development opportunities
  • general: Employee discounts on Sysco products
  • general: Incentive Plan Eligibility
  • general: Relocation assistance (if applicable)

Target Your Resume for "Transportation Supervisor Careers at Sysco - Chicago, Illinois | Apply Now!" , Sysco

Get personalized recommendations to optimize your resume specifically for Transportation Supervisor Careers at Sysco - Chicago, Illinois | Apply Now!. Takes only 15 seconds!

AI-powered keyword optimization
Skills matching & gap analysis
Experience alignment suggestions

Check Your ATS Score for "Transportation Supervisor Careers at Sysco - Chicago, Illinois | Apply Now!" , Sysco

Find out how well your resume matches this job's requirements. Get comprehensive analysis including ATS compatibility, keyword matching, skill gaps, and personalized recommendations.

ATS compatibility check
Keyword optimization analysis
Skill matching & gap identification
Format & readability score

Tags & Categories

TransportationLogisticsManagementSupervisorySupply ChainDistributionCustomer ServiceSafetyComplianceChicagoIllinoisTransportation SupervisorDelivery SupervisorLogistics SupervisorFleet ManagementDOT ComplianceOSHA ComplianceWarehouseTransportation ManagementDelivery OperationsRoute OptimizationDriver ManagementSysco CareersSysco ChicagoChicago JobsIllinois JobsLogistics Jobs ChicagoTransportation Jobs ChicagoManagement JobsSupervisory RolesFleet SupervisorDistribution SupervisorSysco BenefitsDelivery AssociateChicago LogisticsTransportation IndustrySupply Chain ManagementFood ServiceSupply ChainSalesLogistics

Answer 10 quick questions to check your fit for Transportation Supervisor Careers at Sysco - Chicago, Illinois | Apply Now! @ Sysco.

Quiz Challenge
10 Questions
~2 Minutes
Instant Score

Related Books and Jobs

No related jobs found at the moment.