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Trolley

Global payment processing for businesses

Human Resources and Payroll Operations Specialist

Full-TimeUpdated on 10/23/2026
No salary listed
Mid, Senior
Montreal, QC, Canada
HybridHybrid role in Montréal, Québec.
People & HRHR Operations & Coordination, Compensation & Benefits

About the job

Requirements
  • Have 3 to 5 years of experience in People Operations, payroll, human resources operations, or a combination of these areas.
  • Have hands-on experience independently processing Canadian payroll and a strong understanding of Canadian payroll requirements.
  • Have experience processing or supporting U.S. payroll and be comfortable coordinating work with international payroll service providers.
  • Have experience administering employee benefits and working directly with brokers, providers, and employees.
  • Understand payroll accounting, reconciliations, taxable benefits, employee expenses, deductions, and general accounting principles.
  • Have experience with year-end payroll activities and regulatory filings in Canada and the United States.
  • Be highly proficient in Excel and comfortable working with various human resources information systems, payroll, benefits, expense-management, and finance systems.
  • Have exceptional attention to detail and understand the importance of accuracy, confidentiality, and strong controls when handling employee information and financial data.
  • Have an operations-focused approach and enjoy owning processes end to end.
  • Have strong analytical and problem-solving skills and be comfortable investigating discrepancies and finding practical solutions.
  • Communicate clearly and value providing an excellent experience to employees and managers.
  • Be comfortable switching between detailed responsibilities with tight deadlines, such as payroll, and broader People Operations projects.
  • Be proactive and resourceful, and seek ways to improve processes rather than simply maintaining current practices.
  • Be able to manage multiple priorities and deadlines while maintaining attention to detail.
  • Be comfortable working across jurisdictions with colleagues in a multicultural and international environment.
Responsibilities
  • Independently process Trolley's biweekly payroll for employees in Canada and the United States, ensuring accurate and timely payment in accordance with applicable requirements.
  • Coordinate international payroll processing with local providers in Trolley's various markets.
  • Process payroll changes related to new hires, compensation changes, promotions, leaves, departures, bonuses, commissions, taxable benefits, deductions, and other employee changes.
  • Calculate and process commissions and other variable compensation in collaboration with Finance and team leads, validating data and ensuring accurate payments.
  • Prepare and process departure and final-pay requirements, including applicable documents such as T4s, W-2s, 1099s, and Records of Employment.
  • Manage year-end payroll activities and applicable regulatory filings in Canada and the United States.
  • Serve as the primary contact for employee payroll questions and resolve payroll discrepancies as they arise.
  • Ensure compensation changes resulting from salary reviews, promotions, and other compensation decisions are accurately reflected in payroll.
  • Maintain strong payroll controls, documentation, and processes to support accuracy, confidentiality, compliance, and business continuity.
  • Support day-to-day People Operations across the employee lifecycle, ensuring processes are accurate, efficient, and employee-focused.
  • Administer onboarding, promotions, compensation changes, leaves, departures, and other employment changes.
  • Maintain accurate employee information in the human resources information system, payroll and benefits systems, and other People systems.
  • Support employee onboarding and offboarding and continually improve the employee experience at each stage of the company journey.
  • Administer employee programs, including vacation and leave, wellness allowances, recognition and service anniversary gifts, spot awards, and other People & Culture initiatives.
  • Serve as a contact for employees on payroll, benefits, expenses, policies, and other People Operations questions.
  • Support the rollout, communication, and ongoing administration of People programs and policies.
  • Collaborate with the Head of People & Culture on annual and mid-year programs, including salary and merit reviews.
  • Support People reporting, documentation, audits, and other operational needs.
  • Participate in broader People & Culture projects, office administration, employee events, and employee-experience initiatives as business needs evolve.
  • Support administration of Trolley's employee benefits programs across markets, working closely with providers, brokers, and local partners.
  • Manage benefits enrollments and terminations, eligibility changes, employee questions, reporting, invoice reconciliation, and renewals.
  • Coordinate benefits administration across the countries where Trolley operates and help employees understand and access the programs available to them.
  • Participate in annual reviews and benchmarking of benefits programs across markets.
  • Maintain accurate records and processes for benefits, vacation, leaves, and other employee entitlements.
  • Support the implementation and ongoing administration of new benefits and employee programs.
  • Manage the end-to-end employee expense reimbursement process, from submission and review through approval, payment, reconciliation, and appropriate tax treatment.
  • Ensure employee expenses comply with company policies and applicable tax requirements, following up on missing documentation, approvals, or discrepancies.
  • Administer Trolley's travel and expense processes and policies and serve as a contact for employee questions.
  • Identify ways to simplify and improve the employee travel and expense experience.
  • Work with Finance to ensure expenses, reimbursements, payroll items, and company-paid benefits are correctly recorded and reconciled.
  • Prepare required reports on payroll, benefits, expenses, headcount, and other People Operations activities.
  • Reconcile payroll-related accounts and support Finance with month-end and year-end activities.
  • Participate as needed in financial-statement audits and audits related to payroll, benefits, expenses, and compliance.
  • Maintain and improve the systems, processes, documents, and controls that support People Operations.
  • Identify opportunities to automate repetitive tasks, reduce manual work, and improve data quality and accuracy.
  • Find ways to make People processes simpler and more intuitive for employees and managers.
  • Maintain clear documentation and standard operating procedures to support consistency and business continuity.
  • Stay current on payroll, benefits, and employment requirements in the jurisdictions where Trolley operates.
  • Collaborate with People & Culture and Finance teams to resolve operational issues and continually improve ways of working.
Desired Qualifications
  • A PCP or other relevant payroll certification is an asset.

About the company

Trolley provides global payment processing tailored for businesses of all sizes. It offers tools to automate sending and receiving payments, with features for tax compliance, recipient management, and integration with other financial systems. The platform processes transactions securely and streamlines payment workflows, helping businesses save time and reduce complexity. It differentiates itself through a user-friendly interface, strong security measures, and robust customer support, including transparent incident history and status updates. The company’s goal is to enable reliable, efficient cross-border payments to support growth for SMEs, freelancers, and large corporations, and it generates revenue mainly from transaction fees, with optional premium plans for larger or more complex needs.

Company Size

51-200

Company Stage

Series B

Total Funding

$30.7M

Headquarters

Westmount, Canada

Founded

2015

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Simplify's Take

What believers are saying

  • May 2026 Spring release added debit card and wallet payouts, widening use cases.
  • April 22, 2026 Syndicast and July 14, 2026 Tomorrow Music Group expand music-industry traction.
  • Updated 2026 press room signals active shipping, with Amuse and Catapult partnerships.

What critics are saying

  • Tipalti and Dots attack Trolley on speed, rails breadth, and transparent pricing in 2026.
  • June 2026 Thunes dependence hands critical payout reach to an external network partner.
  • Creator and royalty concentration leaves Trolley exposed if SoundCloud, Canva, or Epic Games churn.

What makes Trolley unique

  • June 1, 2026 Thunes integration gives Trolley instant payouts across 140 countries.
  • Trolley bundles onboarding, tax collection, and fraud controls for creator payments.
  • July 14, 2026 music-royalty wins show sticky niche depth across specialized payout workflows.

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Benefits

  • Health Insurance
  • Dental Insurance
  • Vision Insurance
  • Company Equity
  • Paid Vacation
  • Remote Work Options
  • Gym Membership

Growth & Insights and Company News

6 month growth

0%

1 year growth

1%

2 year growth

2%
Fintech News
Jun 3rd, 2026
Thunes partners with Trolley to expand creator economy payouts.

Thunes partners with Trolley to expand creator economy payouts. The integration allows Trolley clients to send instant payments to mobile wallets and bank accounts across 140 countries Get the hottest Fintech Switzerland News once a month in your Inbox Thunes has partnered with Canadian payout provider Trolley to expand international payment options for businesses in the creator economy. Through the integration, Trolley will use the Thunes network to offer its enterprise clients a wider range of local payment methods and instant transfer capabilities. Trolley provides payout infrastructure for platforms including SoundCloud, Canva, and Epic Games. The collaboration is designed to bypass complex regional banking setups, giving Trolley customers direct access to mobile wallets and real-time payment systems. This is particularly relevant for businesses making cross-border payouts to Asia, Africa, and Latin America, where recipients often prefer mobile wallets and real-time payment systems over traditional bank transfers. Retaining talent in the freelance and creator markets increasingly depends on payment speed. According to Trolley, the majority of gig workers prioritise quick access to their funds when choosing a payout system. "Businesses today need to provide specialised, local payment options to attract and keep global talent," said Kyle Rosen, Head of North America at Thunes. "By welcoming Trolley into our network, we are helping platforms deliver the payout flexibility and speed that modern recipients demand." Trolley Founder and CEO Tim Nixon said the partnership allows the company to offer access to local wallets and payment rails that were previously difficult to reach. "Trolley customers can access Thunes' trusted and expansive network while delivering on-demand pay to gig workers and creators exactly when and where they need it," Nixon added. Thunes reports that its direct global network currently reaches 12 billion mobile wallets and bank accounts across 140 countries, supporting transactions in 90 currencies and more than 220 local payment methods through a single integration. Featured image credit: Edited by Fintech News Switzerland, based on image by freepik via Magnific

PR Newswire
Jun 1st, 2026
Trolley partners with Thunes to enable instant global payouts across 140 countries

Trolley, a Canadian global payout platform for the creator economy, has integrated Thunes' Direct Global Network to enable instant international payments to freelancers and creators. The partnership allows Trolley's business customers, including SoundCloud, Canva and Epic Games, to make instant payments across more destinations using preferred local methods. Thunes' network reaches 12 billion mobile wallets and bank accounts across 140 countries in 90 currencies, offering access to over 220 local payment methods through one integration. The collaboration particularly expands access to mobile wallets and real-time payment schemes in Asia, Africa and Latin America. The integration addresses the critical last-mile payment challenge, with 90% of gig workers prioritising quick fund access when choosing payout systems. Trolley customers can now deliver on-demand payments to workers exactly when and where needed.

Spare Music
Jul 14th, 2025
Faster Payouts, Lower Fees: Spare Music Partners with Trolley

SpareMusic LTD has partnered with Trolley to bring you faster payouts, lower fees, and a much smoother experience - so you can spend less time waiting and more time creating.

Nationwide Report
Jun 17th, 2025
OpenPlay and Trolley Sign Partnership to Streamline Royalty Payments for the Global Music Industry

Music catalog management platform and business engine OpenPlay has announced a new collaboration with Trolley, the end-to-end payouts platform for the internet economy.

Business Wire
Nov 15th, 2024
Trolley Secures $23 Million USD Series B to Accelerate Global Payout Platform Expansion

Trolley, a leading global payouts platform, today announced it has raised $23 million USD in a Series B growth equity funding round led by Wavecrest G