About Our Client

Our client is a well-established, growth-oriented transportation and logistics company with a strong reputation for service excellence across North America. Known for a people-first culture, a commitment to its drivers and employees, and a focus on operational excellence, they offer a collaborative environment where leaders are supported, developed, and recognized for their contributions.

Position Overview

The Transportation Planning Supervisor leads the daily operations and performance of our client’s Central Planning Team, ensuring planning objectives are met and operational issues are addressed effectively. Through ongoing communication, coaching, and collaboration with all dispatch staff, this role fosters a high-performing team environment while supporting efficient decision-making and problem resolution. The Supervisor provides guidance on operational concerns, recommends appropriate follow-up actions, and promotes strong working relationships across the organization. This position upholds the company’s policies, culture, procedures, and overall business objectives.

Responsibilities

- Provide leadership, guidance, and day-to-day support to the Central Planning team, fostering a positive, accountable, and high-performing work workplace.
- Oversee planning activities within assigned regions, ensuring operational objectives and departmental goals are achieved.
- Lead the onboarding, training, coaching, and ongoing development of team members and Operations leaders.
- Monitor regional freight and traffic flows, implementing strategies that optimize network balance, efficiency, and service performance.
- Develop a strong understanding of customer operations and requirements to support exceptional service delivery and customer satisfaction.




- Proactively identify operational challenges and implement effective solutions to minimize disruptions and improve performance.
- Partner with Sales to share operational insights, support customer needs, identify business opportunities, and address service concerns.
- Build and maintain strong relationships with drivers, supporting engagement, retention, and operational success in collaboration with Dispatch and Customer Service teams.
- Ensure planning decisions balance operational efficiency, customer commitments, and driver experience.
- Promote continuous improvement, teamwork, and operational excellence across the Planning team.

Qualifications

- 2-3 years of transportation, logistics, or related operational experience, including demonstrated success leading and mentoring a team.
- Strong leadership, organizational, and decision-making skills, with the ability to prioritize competing demands in a fast-paced environment.
- Progressive knowledge of the transportation industry, including North American geography, transportation rules and regulations, competition, and trends.
- Excellent communication, interpersonal, and presentation skills, with the ability to effectively train, mentor, and influence others.
- Strong analytical and problem-solving abilities, with a proactive approach to identifying and resolving operational challenges.
- Experience with safety, compliance, and regulatory requirements related to the transportation industry.
- Proficiency with transportation management systems and Microsoft Office applications, particularly Excel.

Schedule

Monday to Friday, standard business hours. Due to operational requirements, the successful candidate must be prepared to provide leadership coverage outside of regular business hours when needed, including occasional evenings and weekends.

Pay: $75,000.00-$85,000.00 per year

Benefits:

- Dental care
- Extended health care
- Paid time off
- RRSP match
- Vision care

Work Location: In person

📌 Transportation Planning Supervisor (Winnipeg)
🏢 The Certus Group
📍 Winnipeg