People Operations & Payroll Specialist at Trolley in Montréal, Québec

Job description

• 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.

Responsibilities

• In your role, you will:
• 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.
• 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.
• 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.
• 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.
• 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.

Requirements

• 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.

Skills

Required

• Highly proficient in Excel
• Exceptional attention to detail
• Clear communication
• Proactive and resourceful
• Collaborative, team first approach

Benefits

• 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.