Payroll Tax Analyst

Odyssey Reinsurance Company (Odyssey Re) is the global reinsurance arm of Odyssey Group, one of the world’s leading providers of reinsurance and specialty insurance. Odyssey Re offers a broad range of property, casualty, and specialty reinsurance products, providing capital and risk management solutions for clients to efficiently manage economic risk through a network of branch and representative offices across North America, Latin America, EMEA (Europe, Middle East & Africa), Asia Pacific and London.

Odyssey Re is an equal opportunity employer with excellent benefits and a strong commitment to providing training and opportunities for our staff. We provide employees an innovative, enriching environment and take great pride in their career growth.

Odyssey Re is rated A+ (Superior) by AM Best and AA- (Very Strong) by Standard and Poor’s. Odyssey Group is a subsidiary of Fairfax Financial Holdings Limited, which is traded on the Toronto Stock Exchange under the symbol FFH.

Position Summary

The Payroll Tax Analyst is responsible for the oversight and execution of payroll tax compliance and reporting activities across multiple jurisdictions. This role ensures accurate filings, supports audits, monitors regulatory changes, and partners cross-functionally with Payroll, Accounting, and external vendors to maintain compliance and operational integrity. This position works closely under the direction and supervision of the Payroll Director in order to carry out all necessary financial management and fiscal control policies and activities for payroll administration.

Essential Duties

• Ensure compliance with federal, state, and local payroll tax regulations across multi-state operations
• Manage and review quarterly and annual tax filings, including Forms 941, 940, W-2s, and applicable state/local returns
• Serve as the subject matter expert for payroll tax matters and provide guidance on regulatory changes and payroll impacts
• Utilize ADP Smart Compliance to manage payroll tax operations and filings
• Prepare and review payroll tax reconciliations, including quarterly and annual filings
• Partner with Accounting to support payroll tax accruals and general ledger reconciliation
• Maintain accurate payroll records and documentation to support audits and compliance
• Manage payroll tax audits, agency notices, and correspondence with federal, state, and local tax authorities
• Lead resolution of tax discrepancies and inquiries from agencies
• Support internal controls, documentation, and compliance testing requirements (including SOX-style controls)
• Monitor changes in payroll tax laws and assess impact to payroll operations

Qualifications & Experience

• Experience in ADP Enterprise, ADP Smart Compliance and Reporting Required
• Demonstrate high attention to detail with the ability to multi-task
• Must be a self-starter and able to accomplish expected tasks under minimal supervision
• Experience managing multi-state payroll operations
• Strong knowledge of federal, state, and local payroll tax laws and regulations.

Experience & Education Requirements

• Bachelor’s degree in accounting, Finance, Business Administration
• Minimum 10 years of payroll experience, including payroll tax management and compliance
• High Proficiency in Microsoft Office applications and payroll systems.
• Experience with multi-state payroll required (25+ states)
• Strong analytical, problem-solving, and organizational skills.
• Excellent communication and stakeholder management abilities.
• Strong sense of urgency in meeting customer needs
• Very strong personal communication skills

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