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.

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.

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📌 Transportation Planning Supervisor - Dispatch (Manitoba)
🏢 Reimer Associates
📍 Manitoba