Payroll Compliance Analyst - Advanced

Doubtless North America is seeking a highly skilled Payroll Compliance Analyst to serve as a subject matter expert for payroll compliance, governance, risk management, and payroll tax operations across multiple U.S. and Canadian legal entities. This role is responsible for ensuring payroll practices remain compliant with federal, state, provincial, and local regulations while supporting audits, strengthening internal controls, mitigating risk, and driving continuous process improvement. This is a hybrid role with an expectation of 2 days per week in office, based in the New York City office.

Responsibilities

Monitor payroll operations to ensure compliance with applicable federal, state, provincial, and local payroll regulations across the United States and Canada; Research, interpret, and communicate legislative and regulatory changes that impact payroll processes, policies, and controls; Conduct payroll compliance reviews, audits, and control testing to identify compliance risks and process gaps; Support internal and external audits, regulatory examinations, and remediation efforts while maintaining audit-ready documentation; Review employee tax configurations, payroll tax filings, remittances, and reporting requirements for accuracy and compliance; Coordinate responses to agency notices, tax inquiries, and filing discrepancies in partnership with payroll tax vendors and internal stakeholders; Analyze payroll transactions to verify compliance with company policies, regulatory requirements, and pay practices; Investigate and resolve complex payroll compliance issues related to earnings, deductions, benefits, taxes, garnishments, PTO, and final pay calculations; Assist with payroll compliance activities related to acquisitions, new entities, organizational changes, and payroll transitions; Coordinate agency registrations and evaluate payroll compliance implications associated with business integrations; Maintain payroll governance documentation, standard operating procedures, and compliance controls; Recommend and support process improvements, automation opportunities, and technology enhancements that reduce risk and improve efficiency; Analyze payroll data to identify compliance trends, emerging risks, and improvement opportunities; Prepare dashboards, metrics, and executive-level reporting related to compliance, audit readiness, tax operations, and payroll controls

Requirements

8+ years of progressive payroll experience; 3+ years of experience in payroll compliance, payroll tax, audit, risk management, governance, or related functions; Experience supporting complex multi-state payroll environments; Experience supporting Canadian payroll operations; Experience working within multi-entity, high-growth, or multinational organizations; Demonstrated experience managing complex payroll regulatory and compliance matters; Strong knowledge of U.S. federal, state, and local payroll regulations; Strong understanding of Canadian payroll legislation and reporting requirements; Experience with payroll audits, internal controls, compliance monitoring, and risk mitigation; Knowledge of payroll tax regulations, filings, remittances, and year-end reporting; Advanced proficiency with payroll systems, reporting tools, and Microsoft Excel; Exceptional analytical and problem-solving skills; Strong attention to detail and commitment to accuracy; Ability to interpret complex regulations and translate them into actionable business practices; Excellent communication and stakeholder management skills; Strong organizational skills with the ability to manage multiple priorities and deadlines; Continuous improvement mindset with a focus on process optimization and operational excellence

Benefits

Comprehensive full medical, dental and vision insurance; Basic Life Insurance at no cost to the employee; Company paid short-term and long-term disability; 12 weeks of 100% paid Parental Leave; Health Savings Account (HSA); Flexible Spending Accounts (FSA); Retirement savings plan; Personal Paid Time Off; Paid holidays and company-wide Wellness Day off; Paid time off to volunteer at nonprofit organizations; Pet friendly office environment; Commuter Benefits; Group Pet Insurance; On the job training and skills development; Employee Assistance Program (EAP)