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Added 30 mins ago
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Canada Cartage

Billing Supervisor

Oshawa, ON, Canada

Job type: Full-time
Apply by: Nov 1, 2026
Experience: 3–5 years of transportation experience (required)
Posting language: English
Posted: Oct 2, 2026

Apply About employer

Applications open in a new tab.

Original job description

Career Opportunity

Billing Supervisor

Position Summary

The Billing Supervisor supports the day-to-day operations of the Billing team, ensuring the accurate and timely invoicing of customers while assisting with weekly gross driver payroll activities.

This is a hands-on role requiring a strong understanding of transportation billing processes, EDI and TMS systems, and the ability to step in to support the team when needed. The Supervisor is responsible for overseeing work quality, resolving billing discrepancies, and working closely with Operations, IT, and customers to address issues and ensure accuracy.

Location: Oshawa, Ontario

Schedule: Mon-Fri, 40 hours

What you will do

Oversee day-to-day billing activities to ensure accurate and timely invoicing of customers
Support and guide a team of Billing Clerks (approx. 8–10 employees)
Step in to assist with billing and payroll tasks during peak periods, absences, or tight deadlines
Investigate and resolve billing discrepancies, including mismatches between operational data and invoicing
Work closely with Operations to address missing or incorrect data (e.g., reference numbers, accessorial approvals)
Support EDI billing processes and troubleshoot issues related to data mapping and invoice transmission
Assist with weekly gross driver payroll by rating trips based on hours, miles, and contract rates

Ensure proper application of:

Customer rate structures
Fuel surcharges
Accessorial charges
Generate and review reports as required for customer invoicing (including manual adjustments where needed)
Support Credit & Collections by investigating billing disputes and unpaid invoices
Assist with revenue and expense accruals

What You’ll Bring

3–5 years of transportation experience (required)
Experience in billing, dispatch, or operations within a trucking environment
Working knowledge of:
LTL, FTL, and dedicated operations
Owner-operator, agency, and company driver models
Experience using a TMS system (A1, TruckMate, or similar)
Experience with EDI billing processes
Previous supervisory or lead experience

Along with the following Skills & Competencies:

Strong attention to detail in high-volume environments (“match to the penny” mindset)
Ability to troubleshoot and resolve issues independently
Comfortable working cross-functionally and following up with Operations to resolve gaps
Highly organized with the ability to manage multiple priorities
Hands-on approach with willingness to step in and support the team
Strong Excel and data handling skills

We are a top employer!

Canada Cartage has been recognized on the Forbes list of Canada’s Best Employers for six straight years in a row.

Trucking HR has announced that Canada Cartage has again been selected for the 8th year in a row, as one of Canada’s Top Fleet Employers. In addition, we have been recognized as an Employer of Distinction for the 4th year in a row. This serves to reinforce Canada Cartage’s reputation as an employer of high quality.

We’ve been acknowledged by Forbes 2023, as one of Canada’s Best Employers for Diversity

Why you’ll love Canada Cartage

An iconic Canadian company with over 100 years of helping companies grow and succeed in Canada, we provide national dedicated fleet solutions, general freight services, managed transportation, fulfillment & distribution, and home delivery. With a national network of terminals, cross-docks, and distribution centers, we are one of Canada’s largest and most trusted supply chain service providers. Driven to exceed customer expectations, and supported by technology and innovation, we bring simplicity to complex logistics challenges.

We work with intelligent and focused leaders who are driven to create an outstanding customer experience in partnership with Canadian leading brands. Canada Cartage is deep rooted in family values with an entrepreneurial culture where ideas are welcomed, growth is fostered and high performance is championed. A recognized thought leader and founded in 1914, Canada Cartage dominates the industry by delivering innovative fleet solutions.

Come work with an industry leader!

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.

We would like to thank all those expressing an interest in this position; however only the candidates selected for an interview will be contacted.

Apply About employer

More about this job

Responsibilities

Oversee daily billing operations and guide a team of Billing Clerks to ensure accurate, timely customer invoicing, while stepping in to support billing and weekly gross driver payroll as needed. Resolve billing discrepancies and EDI issues, coordinate with Operations, IT, and customers, support credit and collections, and assist with revenue and expense accruals.

Requirements

Requires 3–5 years of transportation experience, including billing, dispatch, or operations in a trucking environment, and experience with EDI billing and a TMS such as A1 or TruckMate. Candidates should understand LTL, FTL, and dedicated operations and driver models, have supervisory or lead experience, and demonstrate strong Excel, attention to detail, organization, troubleshooting, and cross-functional communication skills.

Skills

Transportation Billing
Billing Supervision
EDI Billing
TMS Systems
Invoice Reconciliation
Billing Discrepancy Resolution
Driver Payroll Rating
LTL, FTL, And Dedicated Operations
Customer Rate Structures
Fuel Surcharges
Accessorial Charges
Excel
Data Handling
Cross-Functional Collaboration
Credit And Collections
Revenue And Expense Accruals

Visa sponsorship

Not detected in the job text

Keywords

Transportation Billing
Billing Clerks
EDI
TMS
A1
TruckMate
LTL
FTL
Dedicated Operations
Owner-Operator
Agency Drivers
Company Drivers
Customer Invoicing
Driver Payroll
Trip Rating
Contract Rates
Fuel Surcharges
Accessorial Charges
Billing Discrepancies
Data Mapping
Invoice Transmission
Credit And Collections
Revenue Accruals
Expense Accruals
Excel
Operations
IT
Freight Transportation

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