Fleet Services Specialist

You belong at Day & Ross.

Fleet Services Specialist

Full-Time

Winnipeg, MB

The Fleet Services Specialist is responsible for overseeing and managing the performance of Brokers and their trucks on a daily and a long-term basis, including engagement, retention and Broker relations.

How You'll Help:

• Ensure company, brokers, and drivers adhere to broker agreements, SOPs, safety requirements including driver speed, HOS violations, and work with Compliance to monitor MVI, and MMR.
• Work with the company and brokers to resolve issues, holding all parties accountable to their responsibilities while maintaining broker engagement and satisfaction
• Address brokers' and drivers' concerns; focused on maximum profitability for their units
• Manage miles on each truck to ensure productivity targets and company standards are met including hired contract obligations such as team trucks running as team US trucks running the USA.
• Investigate and address repeat late deliveries, load refusals, and non-compliance with SOPs
• Manage Brokers and driver time off, updating time away and time ready in the system
• Supporting recruiting department on new hires, with job requests, interviews as well as onboarding.
• Ensuring new units/drivers are setup with expected equipment (satellite and camera), documents in hand, apps, drivers and decals started and up to D&R standards.
• Conducting Orientation for new drivers/brokers as required
• Working closely with the safety team on driver training and safety related concerns as identified
• Proactively managing At Risk drivers and Broker to correct issues before they leave.
• Posting and awarding new schedules for given areas following the scheduled assignment policy.
• Manage / support compliance with random drug tests monthly
• Work with brokers on statement issues, missed payments and related concerns.
• Work with drivers in regards to payment concerns or disputes on irregular duties such as working time or customer detention.
• Liaison between driver and/or broker with Safety, Compliance, Recruiting and operations departments as needed
• Other related duties as may be required

Your Skills & Experience:

• Completion of secondary education preferred
• Post-secondary training in logistics or business, an asset
• A suitable combination of education and experience may be considered
• Previous transportation, operations or customer service experience is preferred
• A suitable combination of education and experience may be considered
• Proficient in MS Outlook, Excel & Word; experience with Truckmate, an asset; ability to learn new programs
• Strong communication skills including the ability to relay information (verbal and written) between several parties and deliver a positive customer experience
• Ability to multitask and prioritize in a deadline driven environment; appropriate sense of urgency
• Ability to work independently and to collaborate with others to meet customer expectations.
• Troubleshooting and problem solving skills; the ability to evaluate current situation, respond quickly to changing requirements, execute and escalate accordingly
• Strong team and customer service focus; negotiation and conflict resolution skills
• Demonstrated ability to build and maintain relationships

To apply, visit our Careers page at

If you're chosen for the role, you'll be asked to provide reference and criminal background checks before employment. You'll only be contacted if you're selected for an interview. 

About Day & Ross

From a single truckload of potatoes in the 1950s to a fleet of thousands, Day & Ross has grown to become one of the largest transportation and logistics providers in North America. With over 7,500 team members on and off the road in the US and Canada, we offer a diversified portfolio of freight and delivery solutions, including LTL, Truckload, Residential, Dedicated Fleet Solutions, and Logistics.    

We believe our people are our greatest strength. For over a decade, we've been recognized as one of Canada's Best Managed Companies. We've also been named a Top Company for Women to Work for in Transportation since 2018. Our recognition reflects the family values we share with our parent company, McCain Foods Limited.

As a federally regulated employer, Day & Ross fully supports the principles of employment equity and encourages all qualified members of the designated groups to apply. Day & Ross is committed to ensuring equal access and participation for people with disabilities and meeting their needs in a timely manner. We will do so by removing and preventing barriers to accessibility and by meeting our accessibility requirements under Accessible Canada Regulations and in alignment with our business practices, capabilities, and values.

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