Job Description

Payroll & Benefits Specialist | Brookfield, WI (Onsite to Hybrid)

About the Company

At Old Republic Risk Management, we don’t just support businesses—we help power some of the largest organizations in North America. For decades, we’ve partnered with Fortune 500 companies and industry leaders, pioneering innovative approaches to risk management and insurance solutions. Our culture is grounded in expertise, collaboration, and long-term relationships, creating an environment where every Payroll Specialist plays a meaningful role in our continued success. As a Payroll Specialist, you’ll join a team that values precision, trust, and professional growth while working in a dynamic and supportive workplace.

Duties

The Payroll & Benefits Specialist will administer and oversee bi-weekly payroll operations for multiple entities while ensuring accuracy, compliance, and timely processing. This Payroll & Benefits Specialist role includes analyzing and reconciling payroll, timekeeping, PTO, tax, and benefits data while independently resolving discrepancies and employee issues.  The Payroll & Benefits Specialist will serve as a subject matter expert for payroll, timekeeping, and benefits systems, troubleshoot system issues, coordinate with vendors, and recommend process improvements. Responsibilities also include administering employee benefit programs, supporting retirement and pension activities, reconciling benefit billing, processing qualifying life events, and maintaining employee records and documentation.  In addition, the Payroll & Benefits Specialist will generate payroll and workforce reports, support audits and compliance initiatives, assist with onboarding and employee status changes, and collaborate closely with Human Resources, Finance, leadership, auditors, and external partners

Experience

To succeed as a Payroll Specialist, you should bring an Associate’s or Bachelor’s degree in Human Resources, Accounting, Business, or a related field, along with at least two years of payroll experience. Multi-state payroll experience is highly valued for this Payroll Specialist opportunity. The ideal Payroll Specialist will have hands-on experience with payroll systems and timekeeping platforms, strong analytical skills, and a commitment to accuracy. We’re looking for a Payroll Specialist who can balance technical expertise with strong communication skills, ensuring employees feel supported while maintaining compliance and operational excellence.

Benefits

• Competitive salary
• 401(k) Savings & Profit-Sharing Plan with company match
• Roth investment options & 529 Education Savings Plan
• Employee Referral Bonus Program
• Medical, dental, and vision insurance
• Life, disability, accident, and critical illness coverage
• Pet insurance
• Flexible Spending & Health Savings Accounts
• Calm app subscription
• 37.5-hour standard workweek
• Generous PTO and paid holidays
• Casual business attire
• On-site fitness center (Brookfield)
• Company events, volunteer opportunities, and team outings

Interested?  Click ‘apply’ and follow some very simple steps to get your resume in front of the Talent Acquisition Team. For this position, online skills assessment is required to be taken for Excel 365. As part of the consideration process, a satisfactory score must be achieved on the assessment to continue to be considered. 

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Old Republic Risk Management is an Equal Opportunity Employer and is committed to maintaining a diverse workplace.