Transportation Operations Manager (Winnipeg)

Position Summary

The Transportation Operations Manager is responsible for leading day‑to‑day terminal operations and ensuring the effective delivery of transportation services to customers. This role is accountable for managing people, equipment, and processes efficiently and cost effectively to achieve service, safety, and performance objectives.

The Operations

Manager serves as the primary operational leader on site and plays a critical role in maintaining service continuity, operational readiness, and customer satisfaction.

Schedule

Can vary; typically Monday–Friday. Due to the nature of transportation operations, availability outside of regular business hours is required to support urgent operational matters.

What you will do

• Provide hands on leadership for terminal operations, including drivers, dispatch, and warehouse teams.
• Act as the primary escalation point for operational issues impacting service, safety, customers, or employees.
• Oversee driver scheduling, coverage planning, and verification of hours worked.
• Support dispatch operations as required, including troubleshooting service disruptions and resolving same‑day operational issues.
• Monitor service levels and customer commitments, taking corrective action when performance risks arise.
• Ensure performance goals are met across safety, quality, productivity, and people metrics.
• Promote and enforce Health & Safety standards, operational policies, and compliance requirements.
• Lead recruitment, onboarding, coaching, and performance management of terminal staff; ensure adequate staffing levels are maintained.
• Coordinate with internal partners (fleet, safety, HR, leadership) to support equipment readiness, facility needs, and operational execution.
• Ensure continuity of operations through effective planning, communication, and handoffs, enabling the business to operate smoothly even when not physically on site.
• Maintain explicit, professional, and timely communication with employees, customers, and leadership.

What You’ll Bring

• Minimum of 3 years of Transportation industry experience in operations, dispatch, terminal leadership, or fleet management.
• Proven experience leading or supervising frontline teams in a fast‑paced operational environment.
• Working knowledge of Hours of Service (HOS), TDG, and dispatching processes.
• High school diploma required; post‑secondary education considered an asset.

Skills & Competencies

• Strong leadership, decision making, and analytical skills in real‑time operational environments.
• Demonstrated integrity, trustworthiness, and professionalism, with the ability to operate autonomously and earn confidence from drivers, customers, and leadership.
• High ownership mindset with accountability for outcomes and service performance.
• Ability to proactively identify operational risks and implement solutions before issues escalated.
• Comfortable working in an imperfect, high‑pressure transportation environment where not every scenario has a defined SOP.
• Excellent verbal and written communication skills.
• Ability to manage multiple priorities and remain composed under pressure.
• Willingness to step in and support operations hands on when required.
• Proficiency in MS Office (Outlook, Excel, Word); experience with transportation management systems considered an asset.
• Ability to influence and lead through credibility, consistency, and practical problem solving.

Benefits

Why people love working for Canada Cartage

Cohesive team and a positive, hard‑working atmosphere.

Meaningful opportunities for career growth.

Company‑wide recognition initiatives designed to recognize employees when they demonstrate outstanding customer service, teamwork and our core values.

Perks

Discounted hotels, car rentals, entertainment, gym memberships, phone plans, electronics, to name a few.

Fun events throughout the year, like summer barbeques and driver‑appreciation week that regularly bring us together.

We give back to the communities in which we operate by volunteering and donating to local charities.

Accessibility & Equity

Canada Cartage is committed to adhering to the objectives and requirements outlined in the Accessible Canada Act (ACA). We are determined in meeting the accessibility needs of persons with disabilities in a timely manner, through the implementation of the requirements of the ACA and its applicable regulations. If you require accommodation under the ACA at any point in your application or employment duration, please let us know.

Committed to employment equity, Canada Cartage Systems LP encourages applications from Aboriginal people, members of visible minority groups, and women.