Payroll and Compliance Specialist (Remote)

Overview

A rapidly growing human resources, employee benefits, and business insurance solution provider is seeking an experienced Payroll and Compliance Specialist. This full-time, remote position based in Chicago, IL, involves managing payroll administration and regulatory compliance for a portfolio of clients. The role requires ensuring accurate and timely payroll processing, advising clients on payroll and wage regulations, supporting system implementations, and identifying opportunities to improve operational efficiency.

Responsibilities

• Manage payroll processing for assigned clients, ensuring accuracy, timeliness, and compliance with federal, state, and local regulations.
• Review and reconcile payroll data; investigate discrepancies; complete month-end, quarter-end, and year-end payroll activities.
• Generate payroll reports and provide records, reconciliations, and supporting documentation for client audits and business needs.
• Serve as a trusted advisor on payroll tax compliance, wage and hour laws, internal controls, and payroll administration best practices.
• Respond to payroll-related inquiries from clients, employees, and stakeholders with timely and accurate resolutions.
• Lead or support payroll and HRIS implementations, system upgrades, vendor coordination, and process improvement initiatives.
• Act as the primary liaison between clients and payroll technology vendors, providing end-user support and resolving system-related issues.
• Identify opportunities to streamline payroll processes, improve accuracy, increase efficiency, and enhance the client experience.
• Build and maintain strong client relationships by understanding business objectives and delivering proactive, value-added support.
• Collaborate with HR Consulting and other internal teams to improve workflows, support client retention, and ensure consistent service delivery.
• Maintain current knowledge of payroll regulations, technology developments, and industry best practices.
• Protect confidential payroll, employee, and client information with discretion and professional judgment.

Requirements

• Minimum of 3 years of experience in payroll administration, payroll tax compliance, or related payroll consulting roles.
• Bachelor’s degree in Accounting, Finance, Human Resources, Business Administration, or related field preferred.
• Comprehensive knowledge of payroll processing, reconciliations, reporting, internal controls, payroll taxes, and wage and hour regulations.
• Experience interpreting and applying federal, state, and local payroll laws and compliance requirements.
• Experience managing payroll for multiple clients, business entities, or employee populations preferred.
• Hands-on experience with payroll and HRIS platforms required; experience with Rippling and Paylocity preferred.
• Experience supporting payroll system implementations, upgrades, or operational improvement initiatives preferred.
• Strong analytical, project management, and problem-solving skills with the ability to resolve complex payroll issues.
• Excellent organizational skills and attention to detail; ability to manage competing priorities and deadlines in a fast-paced environment.
• Excellent written, verbal, and interpersonal communication skills; ability to explain payroll and compliance topics clearly.
• Strong client service mindset; ability to work independently and collaborate effectively with internal teams and external partners.
• Proficiency with Microsoft Office Suite and ability to quickly learn and adapt to new technology platforms.
• Fundamental Payroll Certification (FPC) or Certified Payroll Professional (CPP) designation preferred, or willingness to obtain certification.
• Commitment to maintaining confidentiality and handling sensitive payroll and employee information with discretion.

Compensation & Benefits

• Competitive salary
• Medical, Dental, and Vision benefits
• Flexible Spending Account (FSA), Health Savings Account (HSA), and Commuter Transit Programs
• Company-paid Short-Term Disability, Long-Term Disability, and Group Term Life insurance
• Company-paid Employee Assistance Program
• Paid Parental Leave
• Paid holidays
• Personalized Paid Time Off (PTO)
• 401(k) retirement plan

Employees are eligible for benefits coverage the first of the month following 30 days of employment.

Location

This is a full-time remote position for candidates located in Chicago, Illinois.