Billing Supervisor

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.

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
Mississauga

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 and collections by investigating billing disputes and unpaid invoices

Assist with revenue and expense accruals

What You’ll Bring

3–4 years of transportation experience

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 (AI, Truckmate or similar)

Experience with EDI billing processes

Previous supervisory or lead experience

College diploma; or trade apprenticeship certification

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

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.

We are a strong company that weathers the storm through pandemics and recessionary…