Payroll Compliance Analyst - Advanced

Established in 2021, Independence Pet Holdings is a corporate holding company that manages a diverse and broad portfolio of modern pet health brands and services, including insurance, pet education, lost recovery services, and more throughout North America.

We believe pet insurance is more than a financial product and build solutions to simplify the pet parenting journey and help improve the well-being of pets. As a leading authority in the pet category, we operate with a full stack of resources, capital, and services to support pet parents. Our multi-brand and omni-channel approach include our own insurance carrier, insurance brands and partner brands. 

Doubtless North America is hiring a Payroll Compliance Analyst based in our New York City office

This is a hybrid role with an expectation of 2 days per week in office. The successful candidate will reside in the NYC area or will be relocating to the area.

Position Summary

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.

The ideal candidate combines deep payroll compliance expertise with strong analytical capabilities, a proactive approach to problem-solving, and the ability to collaborate effectively across Payroll, Human Resources, Finance, Legal, Benefits, and external service providers.

Key Responsibilities

Drive Payroll Compliance & Regulatory Excellence

• 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.

Strengthen Audit Readiness & Risk Management

• 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.

Lead Payroll Tax Compliance Activities

• 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.

Ensure Accurate Employee Pay Practices

• 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.

Support Organizational Growth & Change

• 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.

Enhance Controls & Operational Effectiveness

• 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.

Deliver Meaningful Reporting & Insights

• 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.

Qualifications

Required Experience

• 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.

Knowledge & Technical Expertise

• 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.

Core Competencies

• 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.

Why Join Doubtless North America?

At Doubtless North America, you'll play a critical role in ensuring payroll compliance and operational integrity across a growing organization. You'll partner with leaders across multiple functions, influence payroll governance and risk management strategies, and contribute to initiatives that improve employee experience, strengthen controls, and support business growth.

Compensation

Base pay range: $91,325 – $114,158 per year. This is the range we reasonably expect to pay at hire. Placement within the range depends on job-related factors such as experience, skills, and certifications. This position is eligible for commission. Base pay is one part of a total rewards package that includes the benefits listed below.

All of our jobs come with great benefits including healthcare, parental leave and opportunities for career advancements. Some offerings are dependent upon the location of where you work and can include the following:

• 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)

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