People Operations & Payroll Specialist

People Operations & Payroll Specialist

Location: Montreal, QC (hybrid)
Reports to: Head of People & Culture

Trolley is looking for a People Operations & Payroll Specialist to join our People & Culture team. This is a broad, hands-on role focused on delivering the day-to-day People Operations programs and processes that support our employees across our global workforce.

You’ll play an important role across the employee lifecycle, with responsibility for People Operations, benefits and employee programs, payroll, travel and expenses, and HR administration. Payroll will represent approximately 30–50% of the role , so we're looking for someone who brings strong hands on payroll experience but is equally excited to take on a broader People Ops mandate.

Working closely with the Head of People & Culture, Finance, managers, employees, and external partners, you'll take ownership of key operational processes, solve problems, improve how we work, and help deliver a great employee experience.

In your role, you will:

Payroll & Compensation Operations

• Independently process Trolley's bi-weekly payroll for employees in Canada and the US, ensuring employees are paid accurately, compliantly, and on time.
• Coordinate international payroll processing with our local payroll providers across our global locations.
• Process payroll changes related to new hires, compensation changes, promotions, leaves, terminations, bonuses, commissions, taxable benefits, deductions, and other employee changes.
• Calculate and process employee commissions and other variable compensation, partnering with Finance and business leaders to validate inputs and ensure accurate payment.
• Prepare and process termination and final pay requirements, including applicable documentation such as T4s, W-2s, 1099s, and Records of Employment (ROEs).
• Manage payroll year-end activities and applicable statutory reporting across Canada and the US.
• Serve as the primary point of contact for employee payroll questions and resolve payroll discrepancies as they arise.
• Ensure compensation changes resulting from merit 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.

People Operations & Employee Experience

• Support the day-to-day delivery of People Operations throughout the employee lifecycle, ensuring our processes are accurate, efficient, and employee-focused.
• Manage employee administration related to onboarding, promotions, compensation changes, leaves of absence, departures, and other employment changes.
• Maintain accurate employee information across our HRIS, payroll, benefits, and other People systems.
• Support employee onboarding and offboarding and continuously look for opportunities to improve the experience at key moments throughout the employee lifecycle.
• Administer employee programs including vacation and time off, wellness allowances, anniversary recognition and gifts, ad-hoc rewards, and other P&C initiatives.
• Act as a go-to resource for employees across payroll, benefits, expenses, policies, and other People Operations questions.
• Support the rollout, communication, and ongoing administration of People programs and policies.
• Partner with the Head of People & Culture on annual and mid-year programs, including compensation and merit reviews.
• Support People reporting, documentation, audits, and other operational requirements.
• Contribute to broader P&C projects, office administration, employee events, and employee experience initiatives as business needs evolve.

Benefits & Employee Programs

• Support the administration of Trolley's employee benefits programs across our global locations, working closely with benefits providers, brokers, and local partners.
• Manage employee enrolments and terminations, eligibility changes, employee inquiries, reporting, invoice reconciliation, and renewals.
• Coordinate benefits administration across the countries in which Trolley operates and help employees understand and access the programs available to them.
• Support the annual review and benchmarking of our benefits programs across our different markets.
• Maintain accurate records and processes related to benefits, vacation, leaves, and other employee entitlements.
• Support the implementation and ongoing administration of new benefits and employee programs.

Travel, Expenses & Financial Operations

• Manage the employee expense reimbursement process end-to-end, 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 (T&E) processes and policies and act as a point of contact for employee questions.
• Look for opportunities to simplify and improve the travel and expense experience for employees.
• Partner with Finance to ensure expenses, reimbursements, payroll, and company-paid benefits are appropriately recorded and reconciled.
• Produce payroll, benefits, expense, headcount, and other People Operations reporting as required.
• Complete payroll-related account reconciliations and support Finance with month-end and year-end activities.
• Support financial statements, payroll, benefits, expense, and compliance audits as required.

Systems & Continuous Improvement

• Maintain and improve the systems, processes, documentation, and controls that support our People Operations function.
• Identify opportunities to automate repetitive work, reduce manual processes, and improve data quality and accuracy.
• Look for 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-related requirements across the jurisdictions in which Trolley operates.
• Collaborate across P&C and Finance to troubleshoot operational issues and continuously improve how we work.

About you:

• You have 3–5 years of experience in People Operations, payroll, HR operations, or a combination of these areas.
• You have hands-on experience independently processing Canadian payroll and a strong understanding of Canadian payroll requirements.
• You have experience processing or supporting US payroll and are comfortable coordinating with international payroll providers.
• You have experience administering employee benefits and working directly with brokers, providers, and employees.
• You understand payroll accounting, reconciliations, taxable benefits, employee expenses, deductions, and general accounting principles.
• You have experience with payroll year-end requirements and statutory reporting in Canada and the US.
• A PCP designation or other relevant payroll certification is considered an asset.
• You are highly proficient in Excel and comfortable working across HRIS, payroll, benefits, expense management, and finance systems.
• You have exceptional attention to detail and understand the importance of accuracy, confidentiality, and strong controls when working with employee and financial information.
• You are operationally minded and enjoy taking ownership of processes from beginning to end.
• You have strong analytical and problem-solving skills and are comfortable investigating discrepancies and finding practical solutions.
• You communicate clearly and care about providing employees and managers with a great experience.
• You are comfortable moving between detailed, deadline driven responsibilities like payroll and broader People Operations projects.
• You are proactive and resourceful, and naturally look for opportunities to improve processes rather than simply maintaining the status quo.
• You can manage competing priorities and deadlines without losing attention to detail.
• You have a collaborative, team first approach.
• You are comfortable working across different jurisdictions and with colleagues in a multicultural, international environment.

What we offer:

• Competitive salary and meaningful equity (ESOP).
• Join an amazing team of diverse people working together on a common mission.
• Extended healthcare benefits including dental, vision, LTD, and more from day one.
• 4 weeks paid vacation per year + public holidays (+ 1 extra vacation day per year of service).
• 30 days remote work from anywhere.
• Sport & wellness allowance.
• Half-day Fridays during the summer.
• Company provided Apple MacBook Pro and Mac gear.

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