Remote Weekend Payroll Jobs in Chicago, IL (NOW HIRING)

About Launchways, A Division of Patriot Growth Insurance Services: Launchways is a rapidly growing human resources, employee benefits and business insurance solution provider located in Chicago. The team is driven by a strong growth-mindset and has been recognized by both Inc and Entrepreneur magazines in their fastest growing company lists. We pride ourselves on being an inclusive community which enables our people to thrive while providing business leaders the resources and guidance they need to fuel their company’s growth. Launchways is backed by Patriot Growth Insurance Services, a top 50 privately held insurance agency with 51 offices and more than 1000 professionals located throughout the country. Learn more at www.launchways.com.

Position Overview: We are seeking an experienced and detail-oriented Payroll and Compliance Specialist to manage payroll administration and regulatory compliance for a portfolio of clients. This role is responsible for ensuring accurate and timely payroll processing, advising clients on payroll and wage regulations, supporting system implementations, and identifying opportunities to improve operational efficiency. The ideal candidate is a trusted advisor with strong payroll expertise, excellent problem-solving skills, and a commitment to delivering responsive, high-quality client service. This position works closely with the HR Consulting team to strengthen client relationships and provide solutions aligned with each organization’s business objectives.

Work Arrangement: This is a full-time, fully remote position.

Professional Responsibilities:

• Manage payroll processing for assigned clients, ensuring transactions are completed accurately, timely, and in accordance with federal, state, and local requirements.
• Review and reconcile payroll data, investigate discrepancies, and 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 while providing timely and accurate resolutions.
• Lead or support payroll and HRIS implementations, system upgrades, vendor coordination, and process improvement initiatives.
• Serve 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 overall 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 while exercising appropriate discretion and professional judgment.

Qualifications and Requirements:

• Minimum of 3 years of experience in payroll administration, payroll tax compliance, or a related payroll consulting role.
• Bachelor’s degree in Accounting, Finance, Human Resources, Business Administration, or a 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, with the ability to manage competing priorities and deadlines in a fast-paced environment.
• Excellent written, verbal, and interpersonal communication skills with the ability to explain payroll and compliance topics clearly.
• Strong client service mindset with the ability to work independently and collaborate effectively with internal teams and external partners.
• Proficiency with Microsoft Office Suite and the 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.

About Patriot Growth Insurance Services: Founded in 2019, Patriot is a growth-focused national insurance services firm that partners with employee benefits and property and casualty agencies across the United States. Patriot is currently ranked as the 25th largest broker in the U.S. by Business Insurance and has been named to the 2025 Inc. 5000 list of fastest-growing companies. With over 2,100 employees operating in 150+ locations across 48 states, Patriot’s collaborative model delivers resources and strategic support to its agencies. Patriot creates true alignment with its partner agencies, and its operating philosophy fosters enhanced career opportunities for its dedicated and professional team. We are committed to working with like-minded individuals who share our vision of creating an insurance agency focused on operational excellence and a relentless pursuit of growth.

Patriot offers the opportunity to be a part of a fast-growing company since its inception. We strive to create a flexible and collaborative environment for our employees, and our goal is to provide enhanced career opportunities for our dedicated and professional team.

In addition to a competitive salary, we provide a comprehensive health and welfare program to employees, family members and domestic partners. Employees are eligible for benefits coverage the first of the month following 30 days of employment. We offer:

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

Pay Range: $75,000 - $85,000 per year depending on experience.

A wide salary range is posted for this position and any job offer is based upon a salary analysis to comply with the required state pay transparency law. The salary analysis considers relevant experience, education, certifications, and seniority as compared to others doing substantially similar work. There is no guarantee an offer will be at the top of the posted range based on the salary analysis.

Patriot Growth Insurance Services is an equal opportunity employer that is committed to diversity and inclusion in the workplace. We prohibit discrimination and harassment of any kind based on race, color, sex, religion, sexual orientation, national origin, citizenship or immigration status, disability, genetic information, pregnancy, or any other protected characteristic as outlined by federal, state, or local laws.

This policy applies to all employment practices within our organization, including hiring, recruiting, promotion, termination, layoff, leave of absence, compensation, benefits, and training. Patriot makes hiring decisions based solely on qualifications, merit, and business needs at the time. For more information, read through our EEO and DE&I Policy located on our website at www.patriotgis.com.