Payroll Specialist (Canada)

HeyMilo•Toronto, ON

7d•Remote

About The Position

HeyMilo builds AI interviewers that automate and improve hiring through conversational AI. We're a growing team with employees and contractors across the US and Canada, and we need someone who keeps our payroll accurate, compliant, and on time. We're hiring a part-time Payroll Specialist to own payroll operations for our Canadian team. You'll run payroll in OrangeHRM, our HRIS, keep employee records clean, handle remittances and year-end reporting, and set the standard for how payroll should work here as we grow. This is a hands-on role with real ownership. You'll work directly with our operations and finance leads, document our payroll processes as you build them, and be the person who catches the error before it hits a paycheque.

Requirements

3+ years of hands-on Canadian payroll experience, including payroll you personally ran within the last 12-18 months
Working knowledge of a payroll or HRIS system such as ADP Workforce Now, Dayforce, Payworks, Wagepoint, QuickBooks Payroll, or Workday. OrangeHRM experience is a plus, not a requirement.
Solid grasp of Canadian payroll compliance: CRA remittances, EI and CPP, provincial employment standards, ROEs, T4 and T4A reporting
Strong attention to detail and the ability to explain why you take each step
Comfortable working independently in a remote team and walking others through your process on screen shares
Reliable computer and a quiet workspace

Nice To Haves

PCP or PLP designation (National Payroll Institute)
Multi-province experience, especially Quebec: Revenu Québec remittances, QPP, QPIP, and RL-1 reporting
Experience setting up payroll processes at a startup or small company
Payroll implementation, audit, or training experience

Responsibilities

Run payroll in OrangeHRM: regular and off-cycle pay runs, new-hire setup, terminations and final pay, retro adjustments, and corrections
Maintain and audit employee records: compensation changes, vacation and leave balances, benefits deductions, garnishments, and direct-deposit details
Keep us compliant: CRA source deductions (income tax, CPP, EI), provincial employment standards, vacation pay, statutory holiday pay, Records of Employment, and year-end T4 and T4A reporting
Reconcile each pay run and resolve discrepancies before anything goes out
Document our payroll processes: what triggers each task, what gets checked, and how results are verified, so the playbook doesn't live only in your head
Define our internal quality bar: required outcomes, acceptable tolerances, and what counts as a material error versus a cosmetic one
Review payroll work for accuracy and flag exactly what went wrong and why when something slips