Transportation Planning Supervisor - Dispatch

Reimer Associates is partnered with a well-established national transportation and logistics organization to recruit a Transportation Planning Supervisor for its Winnipeg operation.

This is an excellent opportunity for an experienced transportation or logistics professional to lead an established team of seven planning specialists supporting regional highway operations across Manitoba and Western Canada.

The successful candidate will bring practical transportation experience, strong people-leadership skills, and the credibility required to lead a knowledgeable and tenured team. This role is well suited to someone who understands the pace and operational demands of trucking and can balance hands-on support with effective delegation and accountability.

Key Responsibilities

• Lead, coach, and support a team of experienced transportation planners
• Oversee central planning activities supporting highway operations across Manitoba and Western Canada
• Coordinate planning activities to promote efficient, safe, and reliable service delivery
• Monitor operational performance and ensure team priorities align with organizational objectives
• Establish clear expectations, provide regular feedback, and promote accountability
• Identify opportunities to improve planning processes, productivity, communication, and service levels
• Support the team in resolving operational challenges and making timely decisions
• Use sound judgment to determine when to provide direct intervention and when to empower team members to manage issues independently
• Collaborate with operations, drivers, customer service, maintenance, and other internal stakeholders
• Monitor key performance indicators and contribute to achieving departmental and company targets
• Maintain a positive, professional, and performance-oriented team environment
• Participate in staffing, training, performance management, and employee-development activities as required
• Ensure planning practices support applicable company policies, operational standards, and safety expectations

Ideal Candidate Profile

• Five to ten years of experience in transportation, logistics, dispatch, fleet operations, or a related field
• Previous supervisory, team-lead, or people-management experience
• Experience in trucking, freight transportation, or highway operations is strongly preferred; relevant transportation and logistics experience will also be considered
• A practical understanding of dispatch planning, transportation coordination, capacity management, and time-sensitive operations
• The confidence and maturity to lead an experienced team without unnecessary micromanagement
• Strong decision-making and problem-solving abilities in a fast-paced operational environment
• Excellent communication and interpersonal skills
• The ability to build productive relationships across departments and levels of an organization
• Strong organizational skills and attention to detail
• Proficiency with transportation-management systems, dispatch software, and Microsoft Office applications

Education and Certifications

A university or college diploma or degree in business, logistics, transportation, supply chain, or a related discipline would be considered an asset. Professional certifications such as CITT or CSCMP would also be considered an asset. Equivalent combinations of education and practical transportation experience will be considered.

Work Environment

This is a full-time, 100% in-office position based in Winnipeg, Manitoba. The successful candidate must be comfortable working in a fast-paced transportation environment and maintaining regular communication with operational teams throughout the day.

How to Apply

If you are an experienced transportation or logistics leader who enjoys developing people, improving operations, and working in a dynamic operational environment, we invite you to apply. Please submit your resume through LinkedIn or contact Reimer Associates for a confidential discussion about this opportunity.

Reimer Associates Inc. thank you for your application and interest in this opportunity. We sincerely appreciate the time you have taken to share your background and experience. We are in the process of reviewing applications and will be moving forward with candidates whose qualifications closely align with client requirements for the role. If you are selected for further consideration, a member of our Team will be in touch with you directly. Due to the high volume of applications we receive, we are unable to respond to each candidate individually. However, we will retain your resume on file and may reach out to you should a suitable opportunity arise in the future.