---
title: 'Payroll Specialist (Canada) at HeyMilo'
canonical: 'https://feeny.ai/job/payroll-specialist-canada-heymilo-toronto-9ncfbjx81327'
type: 'job'
last_seen: '2026-09-09'
---

# Payroll Specialist (Canada) at HeyMilo

- **Company:** HeyMilo
- **Location:** Toronto, Canada
- **Employment:** full-time
- **Work type:** hybrid
- **Posted:** 2026-08-06
- **Last confirmed live:** 2026-09-09
- **Apply:** https://jobs.ashbyhq.com/heymilo/e4a5f093-5d8b-4cb2-aead-0a184e4f27d4

## Job description

Type: Part-time contract, 5-15 hours/week, flexible schedule

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.

## THE ROLE

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.

## WHAT YOU'LL DO

- 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

## WHAT WE'RE LOOKING FOR

- 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

## BONUS

- 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

## DETAILS

- Part-time contract with a flexible schedule you set around payroll deadlines
- Competitive hourly rate
- Direct exposure to how a fast-moving AI company runs its operations
- NDA required

HeyMilo AI is an equal opportunity employer. We welcome applicants from all backgrounds and do not discriminate on the basis of race, religion, colour, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

## About HeyMilo

## Company Overview
- **One-liner**: HeyMilo provides an AI-powered voice and video agent that automates candidate screening and interviewing for high-volume hiring teams.
- **Entity Type**: Private (Seed stage; raised $6M total)
- **Headquarters**: New York, New York, USA
- **Founded**: 2023
- **Founders**: Sabashan Ragavan (Co-Founder & CEO)

## Core Business
- **Primary industry**: AI recruiting / HR technology
- **Target customers**: B2B – staffing firms, enterprises, franchises, recruitment process outsourcing (RPO) firms, and any organization with high-volume hiring needs
- **Mission or purpose**: To fix high-volume hiring by giving employers a faster, fairer, and more consistent way to screen and evaluate every candidate, regardless of background.

## Products & Services
- **AI Interviewer (Voice & Video)**: A conversational AI agent that conducts live interviews, asks follow-ups, and evaluates candidates using customizable rubrics. Supports 17+ languages. (SaaS)
- **Pre-Screening Control**: Configurable eligibility checks, resume screening, and form-based screening to surface best-fit candidates. (SaaS)
- **Candidate Sourcing**: Integrates with ATS and other data sources to pipe in and rank candidates. (SaaS)
- **Insights & Analytics**: Collects structured interview data, tracks performance trends, and feeds insights back into the ATS. (SaaS)
- **Notetaker**: Captures structured notes from recruiter-led interviews for consistent evaluation data. (SaaS)
- **AI Scenario Assessment**: Evaluates how candidates plan, prompt, and assess AI-generated outputs through live scenarios. (SaaS)
- **Candidate Recommendations**: Identifies and ranks previously screened applicants from the ATS. (SaaS)

## Market Standing
- **Valuation/Market Cap**: Not disclosed
- **Key Metric**: Total funding raised = **$6M** (Seed VC - II, announced June 2026) [cbinsights.com](https://www.cbinsights.com/company/heymilo-ai)
- **Notable Investors/Partners**: Investors include Entrepreneurs Roundtable Accelerator, Alumni Ventures, Canaan Partners, and Category Ventures. Customers include Randstad, WilsonHCG, and Neo Financial. [cbinsights.com](https://www.cbinsights.com/company/heymilo-ai)
- **Growth Signals**: Has screened over 1 million candidates; operates a globally distributed team across New York, Toronto, Colombo, Vancouver, Stockholm, Manila, Brasília, and Phoenix; launched three new AI agent capabilities in 2026 (AI Scenario Assessment, Candidate Recommendations, Notetaker). [heymilo.ai](https://www.heymilo.ai/about) | [cbinsights.com](https://www.cbinsights.com/company/heymilo-ai)

## Competitive Advantages
- **Bias‑free, ethical AI**: Uses third‑party bias audit checks and provides a “trust score” to detect cheating, ensuring fair evaluations.
- **High candidate satisfaction**: Average candidate satisfaction score of 4.6/5 [heymilo.ai](https://www.heymilo.ai/).
- **Customizable & contextual**: Interview questions can be tuned with objective evaluation criteria, mimicking a real recruiter’s judgment.
- **Multilingual support**: 17+ languages and local dialects for global recruitment.
- **Deep integrations**: One‑click connections with existing ATS and recruiting tools.

## Strategic Focus
- **Current priorities**: Expanding its agentic recruiting platform with new AI hiring agents (Scenario Assessment, Recommendations, Notetaker) and scaling to serve more high‑volume hiring teams globally. [cbinsights.com](https://www.cbinsights.com/company/heymilo-ai)
- **Direction**: Continue building an “intelligence layer” that handles the entire screening funnel, freeing recruiters to focus on high‑value human judgment.

## Why Work Here
- **Culture**: AI‑native by default – every workflow and product decision assumes AI is a first‑class participant. Values include “team over self,” autonomy with accountability, and shipping decisions without waiting for permission. [heymilo.ai](https://www.heymilo.ai/about)
- **Work model**: Hybrid (offices in New York, Toronto, Colombo, and other cities) with a globally distributed team operating around the clock. [builtin.com](https://builtin.com/company/heymilo-ai)
- **Notable perks**: Emphasis on learning rapidly in a fast‑changing AI landscape; “we hire people who treat every shift as an opportunity to get better.”
- **Open roles** (as of mid‑2026): Senior Software Engineer – Full Stack, Senior Account Executive, SEO & Organic Growth Lead. [builtin.com](https://builtin.com/company/heymilo-ai)

## Sources
1. [heymilo.ai](https://www.heymilo.ai/) – Company homepage and product details
2. [heymilo.ai/careers](https://www.heymilo.ai/careers) – Careers page
3. [heymilo.ai/about](https://www.heymilo.ai/about) – About page, team, and culture
4. [builtin.com](https://builtin.com/company/heymilo-ai) – Built In profile with jobs, offices, and perks
5. [cbinsights.com](https://www.cbinsights.com/company/heymilo-ai) – CB Insights company profile with funding, investors, and news

## Other roles at HeyMilo

- [Payroll Specialist (USA)](https://feeny.ai/job/payroll-specialist-usa-heymilo-new-york-d18wvtvs37pw) — New York, NY
- [Research Engineer, Applied AI](https://feeny.ai/job/research-engineer-applied-ai-heymilo-colombo-v6e0ak4ka5gd) — Colombo, Sri Lanka
- [Research Engineer, Applied AI](https://feeny.ai/job/research-engineer-applied-ai-heymilo-san-francisco-8dx9vkxbw34d) — San Francisco, CA
- [Analyst, Applied AI](https://feeny.ai/job/analyst-applied-ai-heymilo-colombo-4wdspnjsm4fn) — Colombo, Sri Lanka