Manager of Payroll and Benefits (Global)

Accountabilities: Manage the complete payroll process for employees in Canada, the United States, the United Kingdom, and India, ensuring accurate and timely payments in accordance with local legislation. Oversee payroll calendars, employee data changes, off-cycle payments, terminations, and final pay across all four jurisdictions. Manage statutory deductions, tax remittances, regulatory filings, and year-end reporting, including applicable country-specific requirements. Handle government notices, registrations, audits, and payroll compliance obligations, ensuring all deadlines are met. Resolve payroll discrepancies and employee compensation concerns promptly, handling sensitive matters with discretion and empathy. Calculate, administer, and process monthly and quarterly commissions and variable compensation payments. Oversee benefits administration, including employee enrolments, carrier invoices, reconciliations, and renewals in collaboration with external brokers. Serve as a key point of contact for employees and People Operations colleagues on payroll and benefits questions. Prepare and post monthly payroll, bonus, commission, compensation, and benefits accruals and journal entries. Reconcile payroll and benefits activity with the general ledger across multiple currencies and legal entities. Collaborate with Sales and Revenue Operations on monthly commission calculations, variable compensation plans, and related accruals. Prepare monthly, quarterly, and annual payroll and benefits reports for People, Finance, and go-to-market leadership, as well as ad hoc reporting requests. Establish and maintain payroll controls, policies, guidelines, and procedures that support compliance with employment and payroll legislation. Support quarterly reporting requirements and annual external audit requests. Monitor changes in payroll legislation and tax regulations across relevant jurisdictions and proactively implement necessary updates. Identify opportunities to simplify, standardize, and automate payroll and reporting processes, including through the use of AI. Develop and maintain an updated Payroll and Benefits playbook and contribute to dashboards supporting People Operations, Finance, and other teams. Support additional accounting projects and requests as required, while ensuring employee and new-hire information remains accurate across internal systems. Requirements: At least 7 years of experience managing payroll and benefits, including global exposure, with strong Canadian payroll expertise and ideally experience supporting India, the United Kingdom, and the United States. Experience in the technology industry, preferably within a SaaS or sales-led business environment. Canadian Payroll Association designation, such as Payroll Compliance Professional (PCP) or Certified Payroll Manager (CPM). Up-to-date knowledge of Canadian payroll legislation, tax requirements, compensation, and benefits regulations. Strong working knowledge of international payroll processes and statutory compliance, particularly across Canada, the United States, the United Kingdom, and India. Hands-on experience managing commissions and variable compensation calculations and payments. Practical experience with month-end close activities, journal entries, accruals, general ledger reconciliations, and external audit support. Advanced proficiency in Google Sheets or Microsoft Excel. Experience managing payroll and benefits across multiple entities and currencies. Strong written and verbal communication skills, with the ability to manage sensitive or challenging conversations with empathy, honesty, and confidentiality. Excellent organizational skills and the ability to manage competing priorities and strict deadlines without compromising accuracy. A proactive, detail-oriented approach to compliance, problem-solving, and continuous improvement. Interest in leveraging automation and AI tools to improve payroll operations, reporting accuracy, and efficiency. Nice to have: Experience with Dayforce, BambooHR, and Deel. Nice to have: Working knowledge of payroll and benefits requirements in the United Kingdom, United States, and India, or experience managing these processes through Employer of Record (EOR) providers and external payroll partners. Candidates must be based in the Greater Toronto Area or surrounding areas, with the ability to access a downtown Toronto coworking space for occasional team gatherings. Benefits: Base salary range of CAD $110,000–$140,000 annually. Equity opportunities. Remote-first working environment. Flexible coworking options, including access to a downtown Toronto workspace. Comprehensive health and wellness benefits from the first day of employment. Dedicated professional development and learning allowance. MacBook laptop and technology equipment for remote work. Monthly phone and internet subsidy. Work-from-home budget to support a productive home office. Access to Claude to explore AI tools, automate routine tasks, and develop productivity solutions. Supportive remote-first culture with opportunities for virtual connection and collaboration. Regular team town halls, Ask-Me-Anything sessions, and company-wide celebrations. Four Employee Resource Groups offering opportunities for connection and learning. Ongoing manager feedback and regular one-on-one development conversations.