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Full-time
bachelor degree
Health and Dental, Health Care Spending Account, Wellness Account, Short-Term Disability, Long-Term Disability, Life Insurance
Posted 2d ago
Apply by Aug 15
~40 hrs/week
Responsibilities
The Transportation Supervisor leads a team of drivers to ensure safe and efficient delivery operations while managing daily dispatch and vehicle maintenance. This role also focuses on continuous process improvement and monitoring key performance indicators to optimize transportation costs and service levels.
Requirements
Candidates must have at least 5 years of relevant experience or a bachelor's degree in a related discipline. Strong leadership, analytical, and communication skills are required to manage team performance and operational challenges effectively.
Full job description
JOB DESCRIPTION
Purpose
The Transportation Supervisor is responsible for leading a team of drivers and driver helpers, ensuring safe and efficient delivery operations while maintaining compliance with all relevant regulations. This role oversees daily dispatch operations, manages vehicle maintenance, and drives continuous improvement in transportation processes.
Responsibilities
Supervise and guide a team of drivers and driver helpers, providing coaching, feedback, and training.
Conduct performance reviews, address employee concerns, and identify opportunities for team development.
Foster a safe and productive work environment for all team members.
Dispatch Operations:
Manage daily dispatch operations, including route planning, driver assignments, and load balancing.
Monitor driver progress and address any delays or disruptions to delivery schedules.
Optimize routes to minimize travel time, fuel consumption, and delivery costs.
Vehicle Maintenance & Safety:
Oversee vehicle maintenance schedules, ensuring all vehicles are in safe operating condition.
Monitor driver compliance with safety regulations, including hours of service and vehicle inspections.
Investigate and address any safety incidents or accidents.
Performance Monitoring & Improvement:
Monitor key performance indicators (KPIs) related to transportation performance, such as on-time delivery rates, fuel consumption, and driver safety.
Identify areas for improvement in transportation processes and implement corrective actions.
Skills
Leadership & Management: Strong leadership and mentorship skills with the ability to motivate, guide, and develop a high-performing team.
Communication & Interpersonal Skills: Excellent written and verbal communication and interpersonal skills.
Problem-solving: Strong analytical and problem-solving skills with the ability to identify and resolve operational challenges.
Education
Bachelor's degree in related discipline or an additional 4 years of relevant experience in lieu of degree
Experience
5+ years of experience
Physical Demands
While performing the duties of this job, the employee is regularly required to sit, stand, walk and use hands and fingers to operate a computer keyboard, mouse, and telephone to talk and hear.
The employee is frequently required to sit and reach with hands and arms.
Travel Requirements
0-25%
Sysco is committed to Employment Equity. Accommodations during the recruitment process are available upon request for candidates with disabilities.
At Sysco, we aspire to create a global culture that is decidedly diverse, equitable, and inclusive – one where we foster belonging as we care for one another and connect the world through food and trusted partnerships. We are Better Together.
COMPANY 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.
Our Purpose: Connecting the world to share food and care for one another
Our Mission: Delivering success for our customers through industry-leading people, products and solutions
Our Identity: Together we define our future of foodservice and supply chain
Here’s a sample of the many benefits Sysco colleagues enjoy:
Comprehensive Flexible Benefits including Health and Dental, Health Care Spending and Wellness Accounts • Short-Term and Long-Term Disability • Life Insurance • Voluntary Optional Insurance • Parental Leave Plan • Company Pension Plan • Group RRSP & TFSA • Employee and Family Assistance • Stock Purchase Plan • Maple Virtual Care • Unlimited on-line learning • Sysco product discounts • Preferred vendor discounts • Associate Resource Groups
(*benefits may vary based on location or bargaining unit)
ADDITIONAL INFORMATION
This Job Requisition was created with the help of AI. AI will not be used to make hiring decisions or who progresses in the Job Application process. If you have any questions, please reach out to our Talent and Acquisition Team.
Sysco is the global leader in selling, marketing and distributing food and related products to customers who prepare meals away from home. This includes restaurants, healthcare and educational facilities, lodging establishments, entertainment venues, and more. Sysco operates almost 340 distribution centers, in over 10 countries, with 76,000 colleagues serving approximately 730,000 customer locations. The company generated sales of more than $81 billion in fiscal year 2025 that ended June 28, 2025.
As the world’s largest food-away-from-home distributor, Sysco offers customized supply chain solutions, bespoke specialty product offerings, and culinary support to drive customers to innovate and optimize their operations. We act as a trusted business partner to our customers, helping them grow through our industry-leading portfolio that includes fresh produce, premium proteins, specialty products, sustainably focused items, equipment and supplies, and innovative culinary solutions.
For more information, visit www.sysco.com. For important news and key information for Sysco investors, visit the Investor Relations section of the company’s website at investors.sysco.com.
Offices: 1390 Enclave Parkway, Houston, TX 77079, US
marketingfood productsdistributionquality assurancesalessupply chainand truckingMeat and PoultryHospitalityHealth Care
How many Transportation jobs are open in Winnipeg, Canada right now?
There are currently 438 open transportation positions in Winnipeg, Canada listed on Clera. New openings are added daily as companies post roles.
Which companies are hiring for Transportation roles in Winnipeg, Canada?
Companies currently hiring include Ryder Supply Chain Solutions, Perimeter Aviation, Bison Transport Inc., StandardAero, New Flyer, among others. Browse the listings above to see every active employer.
Are there remote or hybrid Transportation jobs in Winnipeg, Canada?
Yes — 31 of the 438 open transportation positions offer remote or hybrid work (2 remote, 29 hybrid).
How do I apply for Transportation jobs in Winnipeg, Canada?
Each listing links directly to the employer's application page. Apply early — fresh listings get the most recruiter attention in the first two weeks.