Fleet Manager

Winnipeg, MB, Canada Full Time

Salary: $50,000 - $60,000

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Fleet Manager

The Fleet Manager has ownership of the overall performance of their fleet. An exceptional Fleet Manager ensures every driver in their fleet is successful and meets productivity and performance expectations of both the driver and management. This means involvement in hiring process, the orientation, and working regularly with our drivers to ensure their success. This position includes certain personnel / management responsibilities, but ultimately is a hands-on position, where the Fleet Manager is responsible for working with drivers and the rest of our operations team to design and dispatch all trip plans for their fleet in a way that is profitable for both the company and the driver.

A strong Fleet Manager is entrepreneurial, a quick thinker, a strong problem solver, exceptional communicator with strong people management skills. They have a detailed technical expertise in over dimensional open deck trucking and can act as a resource to all employees of the company. They thrive in a fast-paced team environment with large call volumes and are able to manage multiple priorities, all while maintaining a positive energy and approach with people. This is a highly-motivated individual that takes initiative to improve and fine tune the plan at all times. They are customer focused, they understand corporate objectives and inspire their team to work towards achieving excellence.

This is an exceptional, highly motivated individual that has a significant influence on the customer experience, the success of our drivers, and ultimately the overall success of our company.

Required Technical Expertise

  • Detailed knowledge of weights and dimensions regulations in all states and provinces that we travel through (ie: allowable axle weights, length, width, height, when permits or pilot cars will be required)
  • Detailed working knowledge of functionality, weights & dimensions of our large variety of trailer types and individual trailers
  • Detailed understanding of the purpose of each of our annual over-dimensional permits, when they can be used, and when additional permits may be required.
  • Detailed knowledge of all permit travel restrictions and permit conditions for all states and provinces that we travel through
  • Detailed working knowledge of customs clearing procedures, both from a customer’s perspective, and our internal procedures, including paperwork requirements, EDI transaction processes, and use of Truckmate.
  • Strong working knowledge of Canada and US Hours of Service rules, including the ability to assist others in trip planning and maximizing productivity.
  • Working knowledge of Canadian and US load securement regulations, as well as practical understanding of securement best practices in typical cargo.

Required Competencies

  • Very organized, strong memory, excellent multi-tasking skills
  • Highly diligent, thorough, with exceptional attention to detail
  • Excellent ability to communicate precise details and complex instructions
  • Strong negotiating skills, both with customers and other employees
  • Passionate, eager to learn, initiative, highly motivated with a sense of urgency
  • Positive attitude that thrives in a team atmosphere
  • Able to work well under pressure
  • Strong computer skills – Outlook, Excel, Word, ability to learn new software
  • Significant long-haul trucking experience required specifically with open deck freight
  • Previous driving experience considered an asset
  • Experience in pricing or spot quoting freight considered an asset

Job Duties

  • Work with operations to plan and dispatch all trips for your fleet, using pre-booked freight as much as possible
  • Source and price out any immediate freight requirements for trucks that do not have a pre-plan or require LTL freight, leveraging other carrier relationships and making calls on available freight from various load postings.
  • Ensure accuracy of all dispatch information in real-time
  • Order all over dimensional permits that are required for each trip
  • Complete all required customs documentation for all drivers in your fleet
  • Develop strong working relationships with all drivers to maintain open lines of communication, identify any concerns, and guide them towards making strong decisions
  • Assist in identifying driver recruiting requirements, and participation in interviews and orientation for new drivers and owner operators.
  • Performs other duties as required


About Wildwood Transport

Our Mission

Deliver the most effortless trucking solution possible.

We are a specialized open deck transportation service provider that exists to help businesses form a trusted, effortless connection with their international supply chain, through a personal, customized approach that leaves every customer with a sense of confidence once we have committed to help.

Our Vision

To be a trusted open deck service provider that is sustainable and widely respected for the strength of its character, and the quality of its work.

Our Commitment to Our Culture

 We will be deliberate in our efforts to build a culture where people are enthusiastic

and optimistic, where we trust each other, and are responsive to each other’s


We will build a safe environment that promotes and supports the small but

important habits that are required to become consistently exceptional.

We will identify and confront attitudes and actions that threaten or undermine this

environment, and we will celebrate and reward people that take the initiative to

support it. 

Apply for position now