Strategic Pay Operations Director - Remote (US/Canada)

Ian Martin Group; United States; Remote; USD 120,000 - 165,000; Full time

Job summary

Raise is seeking a Director of Pay Operations to lead the Canadian and US payroll and accounts payable functions, ensuring compliance, tax accuracy, and scalable processes. As part of Revenue Operations, you will build a high-performing team, drive automation, and partner with Finance to maintain audit-ready standards across North America.

This leadership role focuses on strategic alignment, governance, and capability development for 3,500 workers weekly plus Raise’s internal staff, ensuring

Qualifications

• 10+ years of Canadian and US payroll experience across multiple jurisdictions.
• 3–5 years leading a payroll team at senior/director level.
• Deep expertise in payroll taxation and compliance across employee and contingent workers.
• Monitor payroll legislation changes and assess organizational impact.
• Proven ability to build structure, process, and accountability.
• Demonstrated experience developing people and team capability.
• Systems and process orientation with design for flexibility.
• Calm authority in high-stakes compliance situations.
• Cross-functional influence without requiring formal authority.
• Change leadership in organizational transitions.

Responsibilities

• Lead Canadian and US payroll compliance and tax filings across multiple jurisdictions.
• Ensure AP and payroll delivery aligns with contractual commitments and partner needs.
• Serve as final escalation point on payroll/AP compliance decisions.
• Monitor regulatory changes and translate into actionable process changes.
• Drive automation and process maturity to scale operations.
• Oversee quality and audit readiness of payroll and AP functions.
• Develop and coach Pay Operations teams across levels.
• Partner with Finance, Operations, and Contractor Success to align objectives.

Skills

Payroll leadership

Regulatory compliance

Cross-border payroll

Strategic planning

People development

Automation awareness

Cross-functional influence

Tools

Dayforce

Salesforce

Job description

Raise is seeking a Director of Pay Operations to lead the Canadian and US payroll and accounts payable functions, ensuring compliance, tax accuracy, and scalable processes. As part of Revenue Operations, you will build a high-performing team, drive automation, and partner with Finance to maintain audit-ready standards across North America.

This leadership role focuses on strategic alignment, governance, and capability development for 3,500 workers weekly plus Raise’s internal staff, ensuring