Fleet/Driver Manager

Driver Manager

Location: Winnipeg, MB
Job Type: Full-Time, Permanent
Salary: $45,000–$52,000 per year (Negotiable based on experience and qualifications)
Schedule: 4 Days On / 4 Days Off
Start Date: Immediate

About the Opportunity

Staffmax Staffing & Recruiting is hiring a Driver Manager on behalf of one of our clients in Winnipeg.

We are seeking an experienced and proactive Driver Manager to oversee transportation operations, manage a team of professional drivers, and ensure efficient fleet performance. The successful candidate will be responsible for coordinating and supporting drivers operating across city, regional, and long-haul routes while maintaining high standards of safety, compliance, customer service, and operational efficiency.

This role requires strong leadership, communication, and problem-solving skills, along with experience using transportation management systems to monitor driver activity, optimize scheduling, and maintain real-time communication.

Key Responsibilities

Fleet Planning & Dispatch

• Plan, assign, and dispatch drivers across city, regional, and long-haul routes to maximize fleet utilization and meet customer requirements.

• Coordinate daily transportation activities, including pickups, deliveries, and route planning.

• Monitor driver schedules, load status, ETAs, and PTAs to ensure timely service and proactive issue resolution.

• Utilize transportation management software such as TruckMate, TMW, and Isaac for scheduling, tracking, and real-time communication with drivers.

• Monitor active loads and provide support to drivers throughout their routes.

• Track fleet utilization and prepare operational reports.

• Manage equipment availability and ensure resources are aligned with customer and operational needs.

• Coordinate with internal teams regarding customer requirements, maintenance needs, and operational priorities.

• Identify and resolve service issues quickly to maintain customer satisfaction.

Driver Management & Support

• Manage, coach, and support a team of drivers across various transportation operations.

• Maintain regular communication with drivers through dispatch systems and other communication tools.

• Address driver concerns, performance issues, scheduling conflicts, and operational challenges.

• Ensure drivers follow company policies, safety standards, and Hours of Service (HOS) regulations.

• Support driver retention by building positive working relationships and providing ongoing guidance.

• Review driver performance, mileage, utilization, and productivity metrics.

• Assist with vacation planning, time-off requests, and workforce scheduling.

• Work closely with safety and compliance teams to address training, documentation, and performance requirements.

Operations & Compliance

• Monitor compliance with transportation regulations, safety procedures, and company policies.

• Ensure proper load securement, documentation, and delivery procedures are followed.

• Coordinate equipment inspections and maintenance requirements with the appropriate departments.

• Review operational KPIs and develop action plans to improve driver performance and fleet efficiency.

• Support continuous improvement initiatives within transportation operations.

Key Performance Indicators (KPIs)

• Maintain strong customer satisfaction and minimize service issues.

• Achieve on-time pickup and delivery targets.

• Improve driver engagement, satisfaction, and retention.

• Maximize fleet and equipment utilization.

• Reduce operational delays and improve route efficiency.

• Minimize freight claims and compliance issues.

• Identify opportunities to improve overall transportation performance.

Qualifications

Education & Experience

• High school diploma, post-secondary education, or equivalent combination of education and experience.

• Minimum 2 years of experience in fleet dispatching, transportation operations, logistics, or driver management.

• Previous experience managing professional drivers and coordinating transportation schedules is required.

• Experience supporting city, regional, and long-haul transportation operations is considered a strong asset.

Skills & Abilities

• Strong leadership and driver management skills.

• Excellent communication, organization, and problem-solving abilities.

• Ability to manage multiple priorities in a fast-paced transportation environment.

• Strong decision-making skills with the ability to resolve operational challenges effectively.

• Customer-focused approach with excellent relationship-building skills.

• Proficiency with Microsoft Office Suite, including Outlook, Excel, and Word.

• Experience with transportation management systems such as TruckMate, TMW, and Isaac is highly preferred.

• Knowledge of transportation regulations, Hours of Service (HOS), dispatch procedures, and fleet operations is a strong asset.

Hours of Work

Rotation Schedule: 4 Days On / 4 Days Off

Hours may vary based on operational requirements and transportation schedules.

Working Conditions

• Office-based transportation operations environment.

• Frequent computer, phone, and dispatch system use.

• Fast-paced environment requiring multitasking and quick decision-making.

• Regular communication with drivers and internal operations teams.

What We Offer

• Full-time, permanent position.

• Competitive salary of $45,000–$52,000 annually, negotiable based on experience and qualifications.

• Immediate start available.

• Opportunity to join a growing transportation team.

• Supportive and collaborative work environment.

• Career growth and professional development opportunities.

Staffmax Staffing & Recruiting is committed to providing an inclusive and accessible recruitment process. Accommodations are available upon request throughout the recruitment and selection process.