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Transportation Supervisor Careers at Sysco - Jackson, Wisconsin | Apply Now!

Sysco

Transportation Supervisor Careers at Sysco - Jackson, Wisconsin | Apply Now!

full-timePosted: Feb 17, 2026

Job Description

Transportation Supervisor - Jackson, WI

Role Overview

The Transportation Supervisor position at Sysco Eastern Wisconsin in Jackson, WI, is a crucial role responsible for overseeing the daily operations of the delivery department. This position requires a strong leader who can manage and direct delivery staff, ensure compliance with government regulations, and maintain the safety and security of the delivery operations. The Transportation Supervisor plays a vital role in ensuring that Sysco's products are delivered efficiently and safely to customers, contributing to the overall success of the company.

Day in the Life

A typical day for a Transportation Supervisor at Sysco might involve the following activities:

  • Supervising Delivery Associates and ensuring adherence to standard operating procedures and planned routes.
  • Monitoring compliance with DOT and OSHA regulations, including electronic logging.
  • Managing labor hours and consumable supplies within budget.
  • Preparing work schedules and coordinating extra shifts as needed.
  • Overseeing the proper selection and utilization of company assets in support of the delivery department.
  • Organizing required repairs with the appropriate departments.
  • Reviewing delivery functions and productivity reporting to identify areas for improvement.
  • Interpreting, training, and consistently enforcing company policies and procedures, including food safety protocols.
  • Communicating with Sales Management and Marketing Associates to resolve customer or delivery issues.
  • Visiting customer locations to assess delivery difficulty and address any concerns.
  • Preserving associate relations through regular department or pre-shift meetings.
  • Monitoring associate morale and addressing any issues or concerns.
  • Coordinating with the Safety department to conduct training, associate observations, and accident investigations.
  • Making recommendations for disciplinary action or behavior modification when necessary.
  • Executing management functions such as staff selection, development, performance reviews, and terminations.

Why Jackson, WI?

Jackson, Wisconsin, offers a unique blend of small-town charm and access to larger metropolitan areas. Located in Washington County, Jackson provides a family-friendly environment with excellent schools, parks, and recreational opportunities. The cost of living is reasonable, and the community is known for its strong sense of community and friendly atmosphere. Jackson is also conveniently located near Milwaukee, offering access to a wider range of cultural attractions, dining options, and entertainment venues. Working in Jackson allows you to enjoy a balanced lifestyle, combining a rewarding career with a comfortable and fulfilling personal life.

Career Path

The Transportation Supervisor role at Sysco offers opportunities for career advancement within the company. With experience and demonstrated leadership skills, a Transportation Supervisor can progress to roles such as:

  • Transportation Manager: Overseeing a larger team of supervisors and managing the overall transportation operations for a region or distribution center.
  • Operations Manager: Managing multiple departments within the distribution center, including transportation, warehousing, and customer service.
  • Director of Operations: Providing strategic leadership and direction for all operational activities within the distribution center.
  • Regional Vice President of Operations: Overseeing operations for multiple distribution centers within a geographic region.

Sysco is committed to providing employees with opportunities for professional development and advancement through training programs, mentorship, and leadership development initiatives.

Salary & Benefits

The estimated salary range for a Transportation Supervisor at Sysco Eastern Wisconsin in Jackson, WI, is $60,000 to $85,000 per year. The actual salary may vary depending on experience, qualifications, and performance. Sysco offers a comprehensive benefits package to its employees, including:

  • Comprehensive health insurance (medical, dental, vision)
  • Life insurance
  • Disability insurance
  • Paid time off (PTO)
  • Paid holidays
  • 401(k) retirement plan with company match
  • Employee stock purchase plan
  • Flexible spending accounts (FSA)
  • Health savings accounts (HSA)
  • Wellness programs
  • Employee assistance program (EAP)
  • Tuition reimbursement
  • Employee discounts on Sysco products

Sysco Culture

Sysco is committed to fostering a culture of diversity, inclusion, and respect. The company values its employees and provides a supportive and collaborative work environment. Sysco encourages innovation, teamwork, and continuous improvement. Employees are empowered to make a difference and contribute to the success of the company. Sysco also emphasizes the importance of safety and ethical conduct in all aspects of its operations. The company is dedicated to providing its employees with opportunities for professional growth and development.

How to Apply

Interested candidates can apply for the Transportation Supervisor position at Sysco Eastern Wisconsin through the Sysco Careers website. The online application process involves submitting a resume and cover letter, as well as completing an online assessment. Candidates who meet the qualifications will be contacted for an interview. Sysco is an equal opportunity employer and welcomes applications from all qualified individuals.

FAQ

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

    The Transportation Supervisor is responsible for overseeing the daily operations of the delivery department, managing delivery staff, ensuring regulatory compliance, and maintaining safety and security.

  2. What qualifications are required for this position?

    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 in transportation or delivery is also required.

  3. Is a CDL license required?

    A valid Class A Commercial Driver License (CDL) is preferred but not always required, HazMat certification is also preferred.

  4. What is the salary range for this position?

    The estimated salary range is $60,000 to $85,000 per year, depending on experience and qualifications.

  5. What benefits does Sysco offer?

    Sysco offers a comprehensive benefits package, including health insurance, life insurance, disability insurance, paid time off, a 401(k) retirement plan, and more.

  6. What opportunities are there for career advancement?

    The Transportation Supervisor role can lead to positions such as Transportation Manager, Operations Manager, Director of Operations, and Regional Vice President of Operations.

  7. What is the Sysco culture like?

    Sysco fosters a culture of diversity, inclusion, respect, and collaboration. The company values its employees and provides a supportive work environment.

  8. How can I apply for this position?

    Interested candidates can apply through the Sysco Careers website.

  9. What kind of training is provided?

    Sysco provides training on company policies, safety procedures, and job-specific skills. There are leadership development programs as well.

  10. What are the working hours for this role?

    Working hours will vary depending on the needs of the department, but you can expect to work full time hours and be available to support 24/7 operations.

Locations

  • Jackson, Wisconsin, United States

Salary

Estimated Salary Rangemedium confidence

66,000 - 93,500 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 Managementintermediate
  • Regulatory Compliance (DOT, OSHA)intermediate
  • Budget Managementintermediate
  • Schedulingintermediate
  • Fleet Managementintermediate
  • Repair Coordinationintermediate
  • Productivity Reportingintermediate
  • Efficiency Improvementintermediate
  • Policy Enforcementintermediate
  • Customer Serviceintermediate
  • Communication Skillsintermediate
  • Associate Relationsintermediate
  • Morale Monitoringintermediate
  • Training & Developmentintermediate
  • Performance Managementintermediate
  • Disciplinary Actionintermediate
  • Accident Investigationintermediate
  • Safety Inspectionsintermediate
  • Problem Solvingintermediate
  • Conflict Resolutionintermediate
  • Time Managementintermediate
  • Leadership Skillsintermediate
  • Decision-Making Skillsintermediate
  • Microsoft Office Suiteintermediate

Required Qualifications

  • High school diploma or GED required (experience)
  • Bachelor's degree in Business Management, Supply Chain Management, or related field preferred (experience)
  • 1-3 years of related experience in transportation or delivery (experience)
  • Experience in a supervisory role (experience)
  • Knowledge of DOT and OSHA regulations (experience)
  • Valid Class A Commercial Driver License (CDL) preferred (experience)
  • HazMat certification preferred (experience)
  • Completion of a Sysco-approved defensive driving program (experience)
  • Strong understanding of delivery operations (experience)
  • Ability to manage and motivate a team (experience)
  • Excellent communication and interpersonal skills (experience)
  • Proficiency in Microsoft Office Suite (experience)
  • Ability to work in a fast-paced environment (experience)
  • Strong problem-solving skills (experience)
  • Ability to analyze data and make informed decisions (experience)

Responsibilities

  • Supervise the daily work and safety of Delivery Associates
  • Ensure adherence to standard operating procedures and planned routes
  • Provide safe and efficient customer service
  • Ensure Delivery Associate compliance with local, state, and federal regulatory agencies (DOT, OSHA, etc.)
  • Maintain accurate electronic logs
  • Manage labor hours and consumable supplies within budget
  • Prepare work schedules, including extra work days and shifts
  • 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 the implementation of delivery changes
  • Interpret, train, and enforce company policies, protocols, and procedures
  • Communicate with Sales Management and Marketing Associates to resolve customer or delivery issues
  • Visit customer locations and meet with customers to address issues and assess delivery difficulty
  • Preserve associate relations through regular department meetings
  • Maintain 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
  • Conduct associate observations and routine safety inspections
  • Make recommendations for disciplinary action or behavior modification
  • Execute management functions of staff selection, development, discipline, performance reviews, and terminations
  • Perform the duties of supervised associates and other related duties as needed

Benefits

  • general: Comprehensive health insurance (medical, dental, vision)
  • general: Life insurance
  • general: Disability insurance
  • general: Paid time off (PTO)
  • general: Paid holidays
  • general: 401(k) retirement plan with company match
  • general: Employee stock purchase plan
  • general: Flexible spending accounts (FSA)
  • general: Health savings accounts (HSA)
  • general: Wellness programs
  • general: Employee assistance program (EAP)
  • general: Tuition reimbursement
  • general: Employee discounts on Sysco products
  • general: Opportunities for professional development and advancement
  • general: A supportive and inclusive work environment
  • general: Relocation assistance (if applicable)

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

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Tags & Categories

TransportationSupervisorDeliveryLogisticsManagementFull-timeJacksonWisconsinTransportation SupervisorDelivery ManagementSupply ChainFleet ManagementDOT ComplianceOSHA ComplianceWarehouse OperationsDistribution CenterTransportation JobsDelivery JobsSupervisory RoleJackson WisconsinSysco CareersSysco JobsTransportation Supervisor JobsDelivery Supervisor JobsOperations ManagementTeam LeadershipRoutingSchedulingCustomer ServiceSafety ManagementWisconsin JobsFood ServiceSupply ChainSalesLogistics

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Sysco logo

Transportation Supervisor Careers at Sysco - Jackson, Wisconsin | Apply Now!

Sysco

Transportation Supervisor Careers at Sysco - Jackson, Wisconsin | Apply Now!

full-timePosted: Feb 17, 2026

Job Description

Transportation Supervisor - Jackson, WI

Role Overview

The Transportation Supervisor position at Sysco Eastern Wisconsin in Jackson, WI, is a crucial role responsible for overseeing the daily operations of the delivery department. This position requires a strong leader who can manage and direct delivery staff, ensure compliance with government regulations, and maintain the safety and security of the delivery operations. The Transportation Supervisor plays a vital role in ensuring that Sysco's products are delivered efficiently and safely to customers, contributing to the overall success of the company.

Day in the Life

A typical day for a Transportation Supervisor at Sysco might involve the following activities:

  • Supervising Delivery Associates and ensuring adherence to standard operating procedures and planned routes.
  • Monitoring compliance with DOT and OSHA regulations, including electronic logging.
  • Managing labor hours and consumable supplies within budget.
  • Preparing work schedules and coordinating extra shifts as needed.
  • Overseeing the proper selection and utilization of company assets in support of the delivery department.
  • Organizing required repairs with the appropriate departments.
  • Reviewing delivery functions and productivity reporting to identify areas for improvement.
  • Interpreting, training, and consistently enforcing company policies and procedures, including food safety protocols.
  • Communicating with Sales Management and Marketing Associates to resolve customer or delivery issues.
  • Visiting customer locations to assess delivery difficulty and address any concerns.
  • Preserving associate relations through regular department or pre-shift meetings.
  • Monitoring associate morale and addressing any issues or concerns.
  • Coordinating with the Safety department to conduct training, associate observations, and accident investigations.
  • Making recommendations for disciplinary action or behavior modification when necessary.
  • Executing management functions such as staff selection, development, performance reviews, and terminations.

Why Jackson, WI?

Jackson, Wisconsin, offers a unique blend of small-town charm and access to larger metropolitan areas. Located in Washington County, Jackson provides a family-friendly environment with excellent schools, parks, and recreational opportunities. The cost of living is reasonable, and the community is known for its strong sense of community and friendly atmosphere. Jackson is also conveniently located near Milwaukee, offering access to a wider range of cultural attractions, dining options, and entertainment venues. Working in Jackson allows you to enjoy a balanced lifestyle, combining a rewarding career with a comfortable and fulfilling personal life.

Career Path

The Transportation Supervisor role at Sysco offers opportunities for career advancement within the company. With experience and demonstrated leadership skills, a Transportation Supervisor can progress to roles such as:

  • Transportation Manager: Overseeing a larger team of supervisors and managing the overall transportation operations for a region or distribution center.
  • Operations Manager: Managing multiple departments within the distribution center, including transportation, warehousing, and customer service.
  • Director of Operations: Providing strategic leadership and direction for all operational activities within the distribution center.
  • Regional Vice President of Operations: Overseeing operations for multiple distribution centers within a geographic region.

Sysco is committed to providing employees with opportunities for professional development and advancement through training programs, mentorship, and leadership development initiatives.

Salary & Benefits

The estimated salary range for a Transportation Supervisor at Sysco Eastern Wisconsin in Jackson, WI, is $60,000 to $85,000 per year. The actual salary may vary depending on experience, qualifications, and performance. Sysco offers a comprehensive benefits package to its employees, including:

  • Comprehensive health insurance (medical, dental, vision)
  • Life insurance
  • Disability insurance
  • Paid time off (PTO)
  • Paid holidays
  • 401(k) retirement plan with company match
  • Employee stock purchase plan
  • Flexible spending accounts (FSA)
  • Health savings accounts (HSA)
  • Wellness programs
  • Employee assistance program (EAP)
  • Tuition reimbursement
  • Employee discounts on Sysco products

Sysco Culture

Sysco is committed to fostering a culture of diversity, inclusion, and respect. The company values its employees and provides a supportive and collaborative work environment. Sysco encourages innovation, teamwork, and continuous improvement. Employees are empowered to make a difference and contribute to the success of the company. Sysco also emphasizes the importance of safety and ethical conduct in all aspects of its operations. The company is dedicated to providing its employees with opportunities for professional growth and development.

How to Apply

Interested candidates can apply for the Transportation Supervisor position at Sysco Eastern Wisconsin through the Sysco Careers website. The online application process involves submitting a resume and cover letter, as well as completing an online assessment. Candidates who meet the qualifications will be contacted for an interview. Sysco is an equal opportunity employer and welcomes applications from all qualified individuals.

FAQ

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

    The Transportation Supervisor is responsible for overseeing the daily operations of the delivery department, managing delivery staff, ensuring regulatory compliance, and maintaining safety and security.

  2. What qualifications are required for this position?

    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 in transportation or delivery is also required.

  3. Is a CDL license required?

    A valid Class A Commercial Driver License (CDL) is preferred but not always required, HazMat certification is also preferred.

  4. What is the salary range for this position?

    The estimated salary range is $60,000 to $85,000 per year, depending on experience and qualifications.

  5. What benefits does Sysco offer?

    Sysco offers a comprehensive benefits package, including health insurance, life insurance, disability insurance, paid time off, a 401(k) retirement plan, and more.

  6. What opportunities are there for career advancement?

    The Transportation Supervisor role can lead to positions such as Transportation Manager, Operations Manager, Director of Operations, and Regional Vice President of Operations.

  7. What is the Sysco culture like?

    Sysco fosters a culture of diversity, inclusion, respect, and collaboration. The company values its employees and provides a supportive work environment.

  8. How can I apply for this position?

    Interested candidates can apply through the Sysco Careers website.

  9. What kind of training is provided?

    Sysco provides training on company policies, safety procedures, and job-specific skills. There are leadership development programs as well.

  10. What are the working hours for this role?

    Working hours will vary depending on the needs of the department, but you can expect to work full time hours and be available to support 24/7 operations.

Locations

  • Jackson, Wisconsin, United States

Salary

Estimated Salary Rangemedium confidence

66,000 - 93,500 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 Managementintermediate
  • Regulatory Compliance (DOT, OSHA)intermediate
  • Budget Managementintermediate
  • Schedulingintermediate
  • Fleet Managementintermediate
  • Repair Coordinationintermediate
  • Productivity Reportingintermediate
  • Efficiency Improvementintermediate
  • Policy Enforcementintermediate
  • Customer Serviceintermediate
  • Communication Skillsintermediate
  • Associate Relationsintermediate
  • Morale Monitoringintermediate
  • Training & Developmentintermediate
  • Performance Managementintermediate
  • Disciplinary Actionintermediate
  • Accident Investigationintermediate
  • Safety Inspectionsintermediate
  • Problem Solvingintermediate
  • Conflict Resolutionintermediate
  • Time Managementintermediate
  • Leadership Skillsintermediate
  • Decision-Making Skillsintermediate
  • Microsoft Office Suiteintermediate

Required Qualifications

  • High school diploma or GED required (experience)
  • Bachelor's degree in Business Management, Supply Chain Management, or related field preferred (experience)
  • 1-3 years of related experience in transportation or delivery (experience)
  • Experience in a supervisory role (experience)
  • Knowledge of DOT and OSHA regulations (experience)
  • Valid Class A Commercial Driver License (CDL) preferred (experience)
  • HazMat certification preferred (experience)
  • Completion of a Sysco-approved defensive driving program (experience)
  • Strong understanding of delivery operations (experience)
  • Ability to manage and motivate a team (experience)
  • Excellent communication and interpersonal skills (experience)
  • Proficiency in Microsoft Office Suite (experience)
  • Ability to work in a fast-paced environment (experience)
  • Strong problem-solving skills (experience)
  • Ability to analyze data and make informed decisions (experience)

Responsibilities

  • Supervise the daily work and safety of Delivery Associates
  • Ensure adherence to standard operating procedures and planned routes
  • Provide safe and efficient customer service
  • Ensure Delivery Associate compliance with local, state, and federal regulatory agencies (DOT, OSHA, etc.)
  • Maintain accurate electronic logs
  • Manage labor hours and consumable supplies within budget
  • Prepare work schedules, including extra work days and shifts
  • 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 the implementation of delivery changes
  • Interpret, train, and enforce company policies, protocols, and procedures
  • Communicate with Sales Management and Marketing Associates to resolve customer or delivery issues
  • Visit customer locations and meet with customers to address issues and assess delivery difficulty
  • Preserve associate relations through regular department meetings
  • Maintain 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
  • Conduct associate observations and routine safety inspections
  • Make recommendations for disciplinary action or behavior modification
  • Execute management functions of staff selection, development, discipline, performance reviews, and terminations
  • Perform the duties of supervised associates and other related duties as needed

Benefits

  • general: Comprehensive health insurance (medical, dental, vision)
  • general: Life insurance
  • general: Disability insurance
  • general: Paid time off (PTO)
  • general: Paid holidays
  • general: 401(k) retirement plan with company match
  • general: Employee stock purchase plan
  • general: Flexible spending accounts (FSA)
  • general: Health savings accounts (HSA)
  • general: Wellness programs
  • general: Employee assistance program (EAP)
  • general: Tuition reimbursement
  • general: Employee discounts on Sysco products
  • general: Opportunities for professional development and advancement
  • general: A supportive and inclusive work environment
  • general: Relocation assistance (if applicable)

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

Get personalized recommendations to optimize your resume specifically for Transportation Supervisor Careers at Sysco - Jackson, Wisconsin | 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 - Jackson, Wisconsin | 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

TransportationSupervisorDeliveryLogisticsManagementFull-timeJacksonWisconsinTransportation SupervisorDelivery ManagementSupply ChainFleet ManagementDOT ComplianceOSHA ComplianceWarehouse OperationsDistribution CenterTransportation JobsDelivery JobsSupervisory RoleJackson WisconsinSysco CareersSysco JobsTransportation Supervisor JobsDelivery Supervisor JobsOperations ManagementTeam LeadershipRoutingSchedulingCustomer ServiceSafety ManagementWisconsin JobsFood ServiceSupply ChainSalesLogistics

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

Quiz Challenge
10 Questions
~2 Minutes
Instant Score

Related Books and Jobs

No related jobs found at the moment.