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Payroll Specialist

Canada, Winnipeg Employment contract · Job Posted June 28, 2026
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Job Description

As a Payroll Specialist, you will be responsible for the accurate and timely processing of Canadian and U.S. payrolls for Company Drivers, Owner Operators, Mechanics, and Hourly Office employees. This role requires a strong understanding of payroll processes and compliance requirements, with primary accountability for completing all activities necessary to finalize assigned payrolls. Additional responsibilities include preparing Records of Employment (ROEs), conducting employment verifications, responding to payroll-related inquiries, and supporting payroll accuracy through ongoing monitoring and auditing. The Payroll Specialist will also develop cross-functional knowledge of all payroll streams to provide backup support as required.

Job Responsibility

  • Completing Payrolls – Company Driver Payroll: process end-to-end payroll for company drivers across Canadian and US operations, including multi-state US payroll
  • Verifying and correcting any move #’s for the weekly pay period
  • Settling miles/hours for the pay period and exporting into the Payroll program
  • Ensuring all orientation and Miscellaneous Pay is downloaded properly
  • Entering and validating all miscellaneous deductions into the Payroll program
  • Collecting and importing employee’s earnings into the Payroll program
  • Investigating exception reports for missing legs and/or miles
  • Calculating and processing vacation pay
  • Completing employee verifications
  • Preparing Record of Employment (ROEs) for terminated employees
  • Handling employee inquiries regarding payroll matters across both Canadian and US payroll
  • Managing garnishments in accordance with applicable jurisdictional requirements
  • Processing bonus payouts
  • Assisting in year-end processes
  • Participating in additional projects as assigned by the Payroll Manager/Supervisor, including cross-training
  • Providing guidance and instruction to Payroll Administrators

Requirements

  • 2-3 years' experience in payroll, including multi-state U.S. payroll processing
  • Payroll Compliance Practitioner (PCP) designation is required
  • Post-secondary education related to payroll, accounting, or a related field is considered an asset
  • Previous experience in the transportation/logistics industry is preferred, but not required
  • Strong understanding of payroll legislation across Canadian and U.S. jurisdictions considered an asset
  • Excellent organizational and time management skills, with the ability to prioritize in a high-volume, deadline driven environment
  • High level of accuracy and attention to detail, with a strong aptitude for working with numbers and data
  • Ability to manage multiple tasks and adapt in a fast-paced environment
  • Strong interpersonal and communication skills (both verbal and written)
  • Proficient computer skills, including Microsoft Excel, Word, and Outlook
  • Experience with Great Plains and/or TMW software is considered an asset

Nice to have

  • Post-secondary education related to payroll, accounting, or a related field
  • Previous experience in the transportation/logistics industry
  • Strong understanding of payroll legislation across Canadian and U.S. jurisdictions
  • Experience with Great Plains and/or TMW software

What we offer

  • Supportive team that provides coaching and training to help develop your skills and progress your career
  • Dispersed work environments that promote a healthy work-life balance
  • Meaningful and impactful work and projects with an essential service provider
  • Join our engaging Wellness Program & extracurricular sports teams

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