Resume and JobRESUME AND JOB
Sysco logo

Transportation Supervisor CDLA Careers at Sysco - Fort Myers, Florida | Apply Now!

Sysco

Transportation Supervisor CDLA Careers at Sysco - Fort Myers, Florida | Apply Now!

full-timePosted: Feb 17, 2026

Job Description

Transportation Supervisor CDLA - Fort Myers, FL

Role Overview

The Transportation Supervisor CDLA position at FreshPoint South Florida, a Sysco company located in Fort Myers, Florida, is a critical role responsible for overseeing and supporting the daily operations of the transportation department. This position requires a Commercial Driver's License A (CDLA) and involves supervising transportation associates, ensuring compliance with regulations, and promoting safety and security within the department. The Transportation Supervisor will work closely with the Transportation Manager/Director to optimize delivery and backhaul activities, contributing to the efficient and reliable distribution of fresh produce to Sysco customers.

Day in the Life

A typical day for a Transportation Supervisor CDLA may include the following: * Early Morning Dispatch: Start the day at 2:00 AM, dispatching drivers and providing support to ensure on-time deliveries. * Driver Supervision: Supervise the daily work and safety of transportation associates, ensuring adherence to standard operating procedures, food safety standards, and preferred work methods. * Regulatory Compliance: Ensure transportation associates comply with local, state, and federal regulatory agencies (DOT, OSHA) and that electronic logs are kept current and accurate. * Schedule Management: Prepare work schedules, including extra work days and shifts as needed. * Training and Development: Assist with the training of new associates and cross-training of existing associates. * Fleet Management: Direct the proper selection and utilization of company assets in support of the delivery department. * Coordination and Communication: Coordinate required repairs with proper departments and communicate with warehouse and customer service teams to resolve customer or delivery issues. * Customer Interaction: Visit customer locations to address issues and assess delivery difficulty. * Safety and Security: Work with the safety manager to aid in training, conduct associate observations, and update preferred work methods. Conduct accident investigations to determine root causes. * Administrative Tasks: Review delivery functions and productivity reporting; suggest efficiency ideas and cost reduction measures. Perform management functions of staff selection, development, discipline, performance reviews, and/or terminations. * Team Support: After dispatching is completed, provide flexible support to the Sales team and shuttle drivers as needed.

Why Fort Myers, Florida?

Fort Myers, Florida, offers a unique blend of professional opportunities and a relaxed lifestyle. Located in Southwest Florida, Fort Myers boasts beautiful beaches, a warm climate, and a growing economy. The city provides a vibrant community with access to various outdoor activities, cultural attractions, and family-friendly amenities. Working in Fort Myers offers a lower cost of living compared to other major metropolitan areas, making it an attractive location for both personal and professional growth. Joining Sysco in Fort Myers means becoming part of a supportive community while contributing to a vital part of the food supply chain.

Career Path

The Transportation Supervisor CDLA role at Sysco offers a clear career path for motivated individuals. Starting as a Transportation Supervisor, employees can advance to positions such as Transportation Manager, Logistics Manager, or even Director of Transportation. Sysco is committed to promoting from within and provides numerous training and development opportunities to help employees reach their full potential. The skills and experience gained in this role are highly valuable and transferable, opening doors to a variety of leadership positions within the company.

Salary and Benefits

The estimated salary range for a Transportation Supervisor CDLA in Fort Myers, Florida, is $60,000 to $85,000 per year. Sysco also offers a comprehensive benefits package that includes: * Competitive salary and performance-based bonuses. * Comprehensive health insurance coverage (medical, dental, vision). * Paid time off (PTO) including vacation, holidays, and sick leave. * 401(k) retirement plan with company match. * Employee stock purchase plan. * Life insurance and disability coverage. * Flexible spending accounts (FSAs) for healthcare and dependent care expenses. * Employee assistance program (EAP) for confidential counseling and support. * Wellness programs to promote employee health and well-being. * Tuition reimbursement for continuing education and professional development. * Employee discounts on Sysco products and services.

Sysco Culture

Sysco is a company that values its employees and fosters a culture of teamwork, respect, and integrity. The company is committed to providing a safe and inclusive work environment where employees can thrive. Sysco also prioritizes giving back to the community through various charitable initiatives and volunteer programs. Joining Sysco means becoming part of a company that is dedicated to making a positive impact on the world.

How to Apply

To apply for the Transportation Supervisor CDLA position at FreshPoint South Florida in Fort Myers, Florida, please visit the Sysco careers website. Search for the job title or location and submit your application online. Be sure to include your resume and a cover letter highlighting your relevant experience and qualifications.

Frequently Asked Questions (FAQ)

1. What are the key responsibilities of a Transportation Supervisor CDLA? The Transportation Supervisor CDLA is responsible for supervising transportation associates, ensuring compliance with regulations, promoting safety and security, and optimizing delivery and backhaul activities. 2. What qualifications are required for this position? A high school diploma or GED equivalent is required, and a bachelor's degree in Business Management or Supply Chain Management is preferred. A Commercial Driver's License A (CDLA) is mandatory. 3. What is the typical work schedule for this role? The typical work schedule involves early morning dispatch, starting at 2:00 AM, and may require flexibility to support the Sales team and shuttle drivers. 4. What opportunities for career advancement are available at Sysco? Sysco offers numerous opportunities for career advancement, including positions such as Transportation Manager, Logistics Manager, and Director of Transportation. 5. What benefits does Sysco offer to its employees? Sysco offers a comprehensive benefits package, including health insurance, paid time off, a 401(k) retirement plan, and employee discounts. 6. What is the company culture like at Sysco? Sysco fosters a culture of teamwork, respect, and integrity, and is committed to providing a safe and inclusive work environment. 7. How does Sysco ensure regulatory compliance in its transportation operations? Sysco ensures compliance with local, state, and federal regulations (DOT, OSHA) through regular training, monitoring, and enforcement of company policies and procedures. 8. What role does safety play in the Transportation Supervisor's responsibilities? The Transportation Supervisor plays a critical role in promoting safety by conducting associate observations, updating preferred work methods, and conducting accident investigations. 9. How does Sysco support employee development? Sysco supports employee development through various training programs, tuition reimbursement, and opportunities for career advancement. 10. What is the work environment like in Fort Myers, Florida? Fort Myers offers a relaxed lifestyle with a warm climate, beautiful beaches, and a growing economy, making it an attractive location for both personal and professional growth.

Locations

  • Fort Myers, Florida, 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

  • Transportation Managementintermediate
  • Driver Supervisionintermediate
  • DOT Complianceintermediate
  • OSHA Complianceintermediate
  • Safety Managementintermediate
  • Fleet Managementintermediate
  • Logisticsintermediate
  • Routingintermediate
  • Customer Serviceintermediate
  • Inventory Controlintermediate
  • Warehouse Operationsintermediate
  • Employee Trainingintermediate
  • Performance Managementintermediate
  • Conflict Resolutionintermediate
  • Communication Skillsintermediate
  • Problem-Solvingintermediate
  • Regulatory Complianceintermediate
  • Budget Managementintermediate
  • Schedulingintermediate
  • Accident Investigationintermediate

Required Qualifications

  • High school diploma or GED equivalent required. (experience)
  • Bachelor's degree in Business Management, Supply Chain Management, or a related field preferred. (experience)
  • Commercial Driver's License A (CDLA) required. (experience)
  • Experience in transportation or logistics management preferred. (experience)
  • Knowledge of DOT and OSHA regulations. (experience)
  • Proven supervisory experience. (experience)
  • Strong leadership and communication skills. (experience)
  • Ability to work a flexible schedule, including early mornings. (experience)
  • Proficiency in Microsoft Office Suite. (experience)
  • Excellent problem-solving and decision-making skills. (experience)
  • Ability to manage and prioritize multiple tasks. (experience)
  • Experience with electronic logging devices (ELDs). (experience)
  • Experience with Food Safety standards (experience)

Responsibilities

  • Supervise daily work and safety of transportation associates.
  • Ensure compliance with local, state, and federal regulations (DOT, OSHA).
  • Oversee labor hours and consumable supplies within budget.
  • Prepare work schedules, including extra work days and shifts.
  • Assist with the training of new associates and cross-training of existing associates.
  • Direct the proper selection and utilization of company assets.
  • Coordinate required repairs with proper departments.
  • Review delivery functions and productivity reporting; suggest efficiency ideas and cost reduction measures.
  • Interpret, train, and enforce company policies, protocols, and procedures (food safety, DOT, record keeping).
  • Communicate with warehouse and customer service teams to resolve customer or delivery issues.
  • Visit customer locations and meet with customers to address issues and assess delivery difficulty.
  • Maintain positive associate relations through regular department or pre-shift meetings.
  • Monitor associate morale and submit ideas to improve associate engagement and enablement.
  • Work with safety manager to aid in training, conduct associate observations, and update preferred work methods.
  • Conduct accident investigations to determine root causes and routine safety inspections.
  • Make recommendations for corrective action and/or behavior modification.
  • Perform management functions of staff selection, development, discipline, performance reviews, and/or terminations.
  • Work assigned schedule, exhibit regular and predictable attendance, and work outside of the normal schedule as required.
  • Perform the duties of associates supervised and other related duties as needed.

Benefits

  • general: Competitive salary and performance-based bonuses.
  • general: Comprehensive health insurance coverage (medical, dental, vision).
  • general: Paid time off (PTO) including vacation, holidays, and sick leave.
  • general: 401(k) retirement plan with company match.
  • general: Employee stock purchase plan.
  • general: Life insurance and disability coverage.
  • general: Flexible spending accounts (FSAs) for healthcare and dependent care expenses.
  • general: Employee assistance program (EAP) for confidential counseling and support.
  • general: Wellness programs to promote employee health and well-being.
  • general: Tuition reimbursement for continuing education and professional development.
  • general: Opportunities for career advancement within Sysco.
  • general: Employee discounts on Sysco products and services.
  • general: Relocation assistance (if applicable).
  • general: Training and development programs to enhance skills and knowledge.
  • general: Recognition programs to reward outstanding performance.

Target Your Resume for "Transportation Supervisor CDLA Careers at Sysco - Fort Myers, Florida | Apply Now!" , Sysco

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

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

Check Your ATS Score for "Transportation Supervisor CDLA Careers at Sysco - Fort Myers, Florida | 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

TransportationCDLASupervisorLogisticsFleet ManagementDOTOSHASupply ChainFull-timeManagementDistributionFresh ProduceFort MyersFloridaSupervisory RoleTransportation SupervisorCDLA DriverFort Myers Transportation JobsSysco CareersFreshPoint South FloridaLogistics ManagementDOT ComplianceOSHA RegulationsDriver SupervisionTransportation ManagementDelivery OperationsWarehouse ManagementRouting and SchedulingCommercial DrivingFood DistributionLogistics SupervisorTransportation CoordinatorFleet SupervisorCDL Jobs Fort MyersSysco TransportationTransportation SafetyDriver ManagementRegulatory ComplianceFood ServiceSupply ChainSalesLogistics

Answer 10 quick questions to check your fit for Transportation Supervisor CDLA Careers at Sysco - Fort Myers, Florida | Apply Now! @ Sysco.

Quiz Challenge
10 Questions
~2 Minutes
Instant Score

Related Books and Jobs

No related jobs found at the moment.

Sysco logo

Transportation Supervisor CDLA Careers at Sysco - Fort Myers, Florida | Apply Now!

Sysco

Transportation Supervisor CDLA Careers at Sysco - Fort Myers, Florida | Apply Now!

full-timePosted: Feb 17, 2026

Job Description

Transportation Supervisor CDLA - Fort Myers, FL

Role Overview

The Transportation Supervisor CDLA position at FreshPoint South Florida, a Sysco company located in Fort Myers, Florida, is a critical role responsible for overseeing and supporting the daily operations of the transportation department. This position requires a Commercial Driver's License A (CDLA) and involves supervising transportation associates, ensuring compliance with regulations, and promoting safety and security within the department. The Transportation Supervisor will work closely with the Transportation Manager/Director to optimize delivery and backhaul activities, contributing to the efficient and reliable distribution of fresh produce to Sysco customers.

Day in the Life

A typical day for a Transportation Supervisor CDLA may include the following: * Early Morning Dispatch: Start the day at 2:00 AM, dispatching drivers and providing support to ensure on-time deliveries. * Driver Supervision: Supervise the daily work and safety of transportation associates, ensuring adherence to standard operating procedures, food safety standards, and preferred work methods. * Regulatory Compliance: Ensure transportation associates comply with local, state, and federal regulatory agencies (DOT, OSHA) and that electronic logs are kept current and accurate. * Schedule Management: Prepare work schedules, including extra work days and shifts as needed. * Training and Development: Assist with the training of new associates and cross-training of existing associates. * Fleet Management: Direct the proper selection and utilization of company assets in support of the delivery department. * Coordination and Communication: Coordinate required repairs with proper departments and communicate with warehouse and customer service teams to resolve customer or delivery issues. * Customer Interaction: Visit customer locations to address issues and assess delivery difficulty. * Safety and Security: Work with the safety manager to aid in training, conduct associate observations, and update preferred work methods. Conduct accident investigations to determine root causes. * Administrative Tasks: Review delivery functions and productivity reporting; suggest efficiency ideas and cost reduction measures. Perform management functions of staff selection, development, discipline, performance reviews, and/or terminations. * Team Support: After dispatching is completed, provide flexible support to the Sales team and shuttle drivers as needed.

Why Fort Myers, Florida?

Fort Myers, Florida, offers a unique blend of professional opportunities and a relaxed lifestyle. Located in Southwest Florida, Fort Myers boasts beautiful beaches, a warm climate, and a growing economy. The city provides a vibrant community with access to various outdoor activities, cultural attractions, and family-friendly amenities. Working in Fort Myers offers a lower cost of living compared to other major metropolitan areas, making it an attractive location for both personal and professional growth. Joining Sysco in Fort Myers means becoming part of a supportive community while contributing to a vital part of the food supply chain.

Career Path

The Transportation Supervisor CDLA role at Sysco offers a clear career path for motivated individuals. Starting as a Transportation Supervisor, employees can advance to positions such as Transportation Manager, Logistics Manager, or even Director of Transportation. Sysco is committed to promoting from within and provides numerous training and development opportunities to help employees reach their full potential. The skills and experience gained in this role are highly valuable and transferable, opening doors to a variety of leadership positions within the company.

Salary and Benefits

The estimated salary range for a Transportation Supervisor CDLA in Fort Myers, Florida, is $60,000 to $85,000 per year. Sysco also offers a comprehensive benefits package that includes: * Competitive salary and performance-based bonuses. * Comprehensive health insurance coverage (medical, dental, vision). * Paid time off (PTO) including vacation, holidays, and sick leave. * 401(k) retirement plan with company match. * Employee stock purchase plan. * Life insurance and disability coverage. * Flexible spending accounts (FSAs) for healthcare and dependent care expenses. * Employee assistance program (EAP) for confidential counseling and support. * Wellness programs to promote employee health and well-being. * Tuition reimbursement for continuing education and professional development. * Employee discounts on Sysco products and services.

Sysco Culture

Sysco is a company that values its employees and fosters a culture of teamwork, respect, and integrity. The company is committed to providing a safe and inclusive work environment where employees can thrive. Sysco also prioritizes giving back to the community through various charitable initiatives and volunteer programs. Joining Sysco means becoming part of a company that is dedicated to making a positive impact on the world.

How to Apply

To apply for the Transportation Supervisor CDLA position at FreshPoint South Florida in Fort Myers, Florida, please visit the Sysco careers website. Search for the job title or location and submit your application online. Be sure to include your resume and a cover letter highlighting your relevant experience and qualifications.

Frequently Asked Questions (FAQ)

1. What are the key responsibilities of a Transportation Supervisor CDLA? The Transportation Supervisor CDLA is responsible for supervising transportation associates, ensuring compliance with regulations, promoting safety and security, and optimizing delivery and backhaul activities. 2. What qualifications are required for this position? A high school diploma or GED equivalent is required, and a bachelor's degree in Business Management or Supply Chain Management is preferred. A Commercial Driver's License A (CDLA) is mandatory. 3. What is the typical work schedule for this role? The typical work schedule involves early morning dispatch, starting at 2:00 AM, and may require flexibility to support the Sales team and shuttle drivers. 4. What opportunities for career advancement are available at Sysco? Sysco offers numerous opportunities for career advancement, including positions such as Transportation Manager, Logistics Manager, and Director of Transportation. 5. What benefits does Sysco offer to its employees? Sysco offers a comprehensive benefits package, including health insurance, paid time off, a 401(k) retirement plan, and employee discounts. 6. What is the company culture like at Sysco? Sysco fosters a culture of teamwork, respect, and integrity, and is committed to providing a safe and inclusive work environment. 7. How does Sysco ensure regulatory compliance in its transportation operations? Sysco ensures compliance with local, state, and federal regulations (DOT, OSHA) through regular training, monitoring, and enforcement of company policies and procedures. 8. What role does safety play in the Transportation Supervisor's responsibilities? The Transportation Supervisor plays a critical role in promoting safety by conducting associate observations, updating preferred work methods, and conducting accident investigations. 9. How does Sysco support employee development? Sysco supports employee development through various training programs, tuition reimbursement, and opportunities for career advancement. 10. What is the work environment like in Fort Myers, Florida? Fort Myers offers a relaxed lifestyle with a warm climate, beautiful beaches, and a growing economy, making it an attractive location for both personal and professional growth.

Locations

  • Fort Myers, Florida, 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

  • Transportation Managementintermediate
  • Driver Supervisionintermediate
  • DOT Complianceintermediate
  • OSHA Complianceintermediate
  • Safety Managementintermediate
  • Fleet Managementintermediate
  • Logisticsintermediate
  • Routingintermediate
  • Customer Serviceintermediate
  • Inventory Controlintermediate
  • Warehouse Operationsintermediate
  • Employee Trainingintermediate
  • Performance Managementintermediate
  • Conflict Resolutionintermediate
  • Communication Skillsintermediate
  • Problem-Solvingintermediate
  • Regulatory Complianceintermediate
  • Budget Managementintermediate
  • Schedulingintermediate
  • Accident Investigationintermediate

Required Qualifications

  • High school diploma or GED equivalent required. (experience)
  • Bachelor's degree in Business Management, Supply Chain Management, or a related field preferred. (experience)
  • Commercial Driver's License A (CDLA) required. (experience)
  • Experience in transportation or logistics management preferred. (experience)
  • Knowledge of DOT and OSHA regulations. (experience)
  • Proven supervisory experience. (experience)
  • Strong leadership and communication skills. (experience)
  • Ability to work a flexible schedule, including early mornings. (experience)
  • Proficiency in Microsoft Office Suite. (experience)
  • Excellent problem-solving and decision-making skills. (experience)
  • Ability to manage and prioritize multiple tasks. (experience)
  • Experience with electronic logging devices (ELDs). (experience)
  • Experience with Food Safety standards (experience)

Responsibilities

  • Supervise daily work and safety of transportation associates.
  • Ensure compliance with local, state, and federal regulations (DOT, OSHA).
  • Oversee labor hours and consumable supplies within budget.
  • Prepare work schedules, including extra work days and shifts.
  • Assist with the training of new associates and cross-training of existing associates.
  • Direct the proper selection and utilization of company assets.
  • Coordinate required repairs with proper departments.
  • Review delivery functions and productivity reporting; suggest efficiency ideas and cost reduction measures.
  • Interpret, train, and enforce company policies, protocols, and procedures (food safety, DOT, record keeping).
  • Communicate with warehouse and customer service teams to resolve customer or delivery issues.
  • Visit customer locations and meet with customers to address issues and assess delivery difficulty.
  • Maintain positive associate relations through regular department or pre-shift meetings.
  • Monitor associate morale and submit ideas to improve associate engagement and enablement.
  • Work with safety manager to aid in training, conduct associate observations, and update preferred work methods.
  • Conduct accident investigations to determine root causes and routine safety inspections.
  • Make recommendations for corrective action and/or behavior modification.
  • Perform management functions of staff selection, development, discipline, performance reviews, and/or terminations.
  • Work assigned schedule, exhibit regular and predictable attendance, and work outside of the normal schedule as required.
  • Perform the duties of associates supervised and other related duties as needed.

Benefits

  • general: Competitive salary and performance-based bonuses.
  • general: Comprehensive health insurance coverage (medical, dental, vision).
  • general: Paid time off (PTO) including vacation, holidays, and sick leave.
  • general: 401(k) retirement plan with company match.
  • general: Employee stock purchase plan.
  • general: Life insurance and disability coverage.
  • general: Flexible spending accounts (FSAs) for healthcare and dependent care expenses.
  • general: Employee assistance program (EAP) for confidential counseling and support.
  • general: Wellness programs to promote employee health and well-being.
  • general: Tuition reimbursement for continuing education and professional development.
  • general: Opportunities for career advancement within Sysco.
  • general: Employee discounts on Sysco products and services.
  • general: Relocation assistance (if applicable).
  • general: Training and development programs to enhance skills and knowledge.
  • general: Recognition programs to reward outstanding performance.

Target Your Resume for "Transportation Supervisor CDLA Careers at Sysco - Fort Myers, Florida | Apply Now!" , Sysco

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

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

Check Your ATS Score for "Transportation Supervisor CDLA Careers at Sysco - Fort Myers, Florida | 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

TransportationCDLASupervisorLogisticsFleet ManagementDOTOSHASupply ChainFull-timeManagementDistributionFresh ProduceFort MyersFloridaSupervisory RoleTransportation SupervisorCDLA DriverFort Myers Transportation JobsSysco CareersFreshPoint South FloridaLogistics ManagementDOT ComplianceOSHA RegulationsDriver SupervisionTransportation ManagementDelivery OperationsWarehouse ManagementRouting and SchedulingCommercial DrivingFood DistributionLogistics SupervisorTransportation CoordinatorFleet SupervisorCDL Jobs Fort MyersSysco TransportationTransportation SafetyDriver ManagementRegulatory ComplianceFood ServiceSupply ChainSalesLogistics

Answer 10 quick questions to check your fit for Transportation Supervisor CDLA Careers at Sysco - Fort Myers, Florida | Apply Now! @ Sysco.

Quiz Challenge
10 Questions
~2 Minutes
Instant Score

Related Books and Jobs

No related jobs found at the moment.