Transportation Planning Supervisor
Winnipeg, MB (On-site) · Full-time · On-site · Permanent · $70,000 - $85,000 CAD + bonus · Ref CSC-2026-249
A Transportation Planning Supervisor role at the Winnipeg head office of a leading North American asset-based truckload carrier. You would lead the Central Planning group, the team that plans the routes and balances freight across the network, and keep it hitting its targets day to day.
This is a hands-on, working supervisor role. You'll lead a team of 7 highway planners (plus a few new-grad trainees), and you'll know when to jump in and plan alongside them and when to step back and lead. The role reports to the Manager of Planning and works closely with Dispatch, Driver Managers and Customer Service. It is open because the previous supervisor was promoted.
Schedule & location
Permanent, full-time, on-site at head office in Winnipeg. Monday to Friday, 8am-5pm CST. The planning group covers multiple shifts, so occasional evening or weekend leadership coverage is part of the job.
What you'll be doing
- Lead, coach and develop the Central Planning team: one-on-ones, performance management, onboarding and training
- Oversee planning for your region and make sure operational targets are met
- Monitor freight and traffic flows and act to keep the network balanced and efficient
- Solve operational problems before they become service failures
- Balance efficiency, customer commitments and the driver experience in every planning decision
- Partner with Sales, Dispatch and Customer Service on customer needs and opportunities
- Build trusted relationships with drivers to support engagement and retention
What we're looking for
- 2-3 years of transportation, logistics or related operations experience, including 2+ years leading a team
- Planning, dispatch or load planning background with an asset-based carrier, 3PL or forwarder
- Confident and approachable; comfortable leading strong personalities
- Strong analytical, problem-solving and decision-making skills
- Knowledge of North American geography and transportation rules and regulations
- TMS experience and intermediate Excel
Compensation
- $70,000 - $85,000 CAD base salary
- Annual planning incentive bonus (up to $5,000)
- Benefits and RRSP matching
Responsibilities
- Lead and coach a team of 7 highway planners
- Oversee regional planning and hit operational targets
- Balance freight and traffic flows across the network
- Step in and plan hands-on when the team needs it
- Partner with Dispatch, Driver Managers, Customer Service and Sales
Requirements
- 2-3 years in transportation or logistics operations, with 2+ years leading a team
- Planning or dispatch experience with a carrier, 3PL or forwarder
- Strong analytical and decision-making skills
- TMS experience and intermediate Excel
- On-site in Winnipeg, with occasional evening or weekend coverage