Senior Payroll and Accounting Specialist

About Messagepoint

Messagepoint is a privately owned software company providing an AI-powered SaaS solution that enables enterprises to manage and personalize customer communications with greater speed, accuracy, and control. Our award-winning platform empowers business users to create and optimize compliant, personalized communications across digital and print channels using advanced content intelligence and large language models.

Messagepoint is headquartered in Toronto, with employees located throughout Canada, the United States, France, and the United Kingdom.

About the Role

Messagepoint is seeking a detail-oriented and highly organized Senior Payroll and Accounting Specialist to support payroll and finance operations across Canada and the United States.

This role is responsible for Canadian and U.S. payroll processing, accounts payable, accruals, cash management, reconciliations, payroll-tax and employer registrations in multiple jurisdictions, audit schedules, month-end and year-end reporting, and monitoring the accuracy of employee benefit billings. The ideal candidate combines advanced Canadian and U.S. payroll knowledge with hands-on accounting operations experience and thrives in a results-oriented, collaborative environment. This position requires a high degree of accuracy, confidentiality, accountability, and the ability to organize and prioritize multiple responsibilities according to strict payroll, payment, reporting, and compliance deadlines.

What You’ll Do

Payroll and Employee Administration

• Support semi-monthly Canadian and U.S. payroll processing, including payroll submissions, remittances, reconciliations, adjustments, and journal entries.
• Maintain payroll documentation related to new hires, terminations, compensation changes, payroll deductions, and employee records.
• Manage complex payroll-tax, withholding, unemployment insurance, and employer account registrations when employees are hired in new Canadian provinces or U.S. states.
• Monitor payroll compliance requirements and assist with resolving payroll-tax notices, discrepancies, and account-related matters.
• Monitor and verify the accuracy of employee benefit billings, including reviewing invoices against employee enrolment and coverage information and following up on discrepancies.
• Responsible for year-end payroll and compliance requirements, including T4’s, and W-2’s using Dayforce, 1099s, EHT filings, workers’ compensation reporting, and 401(k) compliance support.

Accounts Payable and Cash Management

• Monitor cash balances and online banking activity to ensure adequate funding for payroll, vendor payments, and other business obligations.
• Support short-term cash-management activities and provide accurate cash information to the Finance team.
• Manage vendor invoices through Stampli, including coding, routing for approval, resolving discrepancies, and preparing invoices for payment.
• Prepare and process vendor payments through approved online banking platforms.
• Review contractor invoices against approved timesheets before processing and payment.
• Review employee expense reimbursements for accuracy, supporting documentation, compliance with Company policies, and proper account allocation.
• Reconcile corporate credit card transactions and obtain supporting documentation for expense allocation and month-end posting.
• Review accounts payable aging reports for accuracy and follow up on outstanding or unusual items, including HST-related postings.

Accounting and Month-End Support

• Process customer receipts and post transactions accurately in Sage Intacct.
• Perform monthly bank reconciliations and investigate and resolve discrepancies.
• Prepare recurring, adjusting, payroll, and other journal entries.
• Accrue unbilled expenses, contractor costs, and other liabilities as part of the month-end close process.
• Support account reconciliations and maintain accurate financial records and supporting documentation.
• Assist with month-end and year-end close activities as required.

Audit and Compliance Support

• Prepare and maintain payroll, accounts payable, cash, and other accounting schedules required for internal and external audits.
• Compile supporting documentation and respond to audit requests accurately and within established timelines.
• Support payroll reporting, financial reporting, and statutory compliance requirements across Canada and the United States.
• Maintain organized and complete records to support financial audits, payroll audits, tax filings, and regulatory reviews.
• Assist with other finance, payroll, accounting, and compliance projects as required.

What You Bring

• Postsecondary education in Accounting, Finance, Payroll Administration, Business Administration, or a related field.
• A minimum of five years of progressive payroll and accounting experience.
• Demonstrated experience managing Canadian and U.S. payrolls, including multi-state U.S. payroll.
• Knowledge of Canadian and U.S. payroll legislation and registrations, including taxation, withholding requirements, source deductions, remittances, and statutory reporting.
• Hands-on experience registering and maintaining payroll-tax, unemployment insurance, withholding, and employer accounts across multiple U.S. states and Canadian jurisdictions.
• Experience managing payroll-tax notices, jurisdictional changes, employee tax setups, and payroll-related account discrepancies.
• Experience with accounts payable, cash management, bank and account reconciliations, journal entries, audit schedules, and month-end close processes.
• Hands-on experience with payroll, expense-management, and financial systems such as Sage Intacct, Dayforce, Stampli, Expensify, and online banking platforms.
• Strong proficiency in Microsoft Excel and other Microsoft Office applications.
• Excellent organizational skills and a high level of attention to detail and accuracy.
• Demonstrated ability to organize and prioritize multiple responsibilities according to strict payroll, payment, reporting, and compliance deadlines.
• Ability to manage confidential and sensitive information with discretion and professionalism.
• Strong communication, problem-solving, and collaboration skills.

Nice to Have

• Experience working in a multi-entity, multi-jurisdictional, or cross-border environment.
• Experience supporting a SaaS or technology company.
• Experience working with employees and payroll accounts across several Canadian provinces and U.S. states.

How We Work

Workplace:Hybrid work model, with one day per week in the office and four days of remote-work flexibility.

Messagepoint is an Equal Opportunity Employer and is committed to fostering diversity, equity, and inclusion in the workplace.

We thank all applicants for their interest; however, only those selected for an interview will be contacted.