Payroll Specialist

At Work Friendly, we help businesses of all sizes and stages build and retain their most valuable asset: their people. We’re a Chicago-based, female-founded and female-run HR and Talent Acquisition consulting firm. We act as a fractional extension of our clients’ People functions—whether as a Head of People, HR Business Partner, HR Generalist, Talent Lead, or Recruiter.

Our work is hands‑on, high‑impact, and relationship‑driven. We specialize in supporting early‑stage startups through strategic growth, but our clients span industries and sizes. No matter the client, our focus remains the same: providing thoughtful, practical, and people‑first HR solutions.

We’re looking for a detail‑oriented and proactive Payroll Specialist who lives and breathes payroll. This role is dedicated exclusively to supporting our Work Friendly clients with payroll and is perfect for someone who finds genuine satisfaction in precision, compliance and keeping every cycle running flawlessly. As a detail‑obsessed, proactive payroll expert, you’ll bring deep expertise in payroll management, compliance, and HR systems.

Reporting to a member of our senior leadership team, you’ll serve as a trusted advisor to multiple clients, guiding them through both strategic payroll initiatives and hands‑on execution. You’ll play a key role in optimizing payroll processes, ensuring accuracy and compliance, and leveraging HRIS software to drive efficiency and data integrity across all people operations. If payroll is your happy place, and you thrive in a role where it’s the main event, not a side task - you’ll fit right in!

While this is a remote position, we are currently only considering candidates who are located in Illinois, Wisconsin, or Michigan.

• Client‑Focused Payroll Consulting
• Serve as a fractional resource for multiple clients, offering support on payroll strategy, system configuration, and best practices across various HRIS and payroll platforms.
• Manage or support payroll processing, including setup of schedules, tax codes, deductions, and adjustments.
• Build payroll processes, SOPs and governance for clients who need structure in their payroll process.
• Configure and run payroll reports in order to audit processes and provide key data to leadership.
• Validate payroll accuracy and compliance with country, federal, state, and local regulations.
• Partner with client leadership to assess current payroll processes, identify gaps, and implement effective solutions that align with business goals.
• Provide guidance and hands‑on support in navigating complex payroll challenges.
• Deliver high‑touch client service and serve as a point of contact for ongoing payroll support.
• Support broader HR initiatives such as performance, benefits, employee relations, talent strategy, and compliance.

• 8+ years of experience in payroll administration in a multi‑state environment
• Ideal candidates have or are pursuing one of the following certifications:
  American Payroll Association's (APA) Certified Payroll Professional (CPP) and Fundamental Payroll Certification (FPC)
• Payroll and timekeeping knowledge—state laws and compliance
• Experience supporting multiple clients or business units at a time
• Strong proficiency in HRIS and payroll systems (e.g., Rippling, ADP, Paylocity, Gusto, Workday, or similar).
• Intermediate to advanced Excel skills, including the ability to build complex formulas and functions, create dynamic reports and work with large data sets from multiple sources.
• Solid understanding of multi‑state payroll processing, wage and hour laws, and payroll tax compliance.
• Strong understanding of how HR compliance interacts with payroll, including FLSA, FMLA, and ADA.
• Excellent project management and organizational skills.
• Confident communicator with the ability to engage executive stakeholders.
• Collaborative team player who can also work independently.
• Proactive problem‑solver who loves building from scratch.
• Deeply client‑focused and service‑minded.
• Bonus:
  Multi‑country payroll experience.

Fully remote role (with optional access to our Chicago West Loop office)
Quarterly in‑person offsites to build connection and collaboration
Health and dental insurance
Paid parental leave
401(k) with competitive employer match
Quarterly performance‑based bonus
Annual learning and development stipend of $500
Flexible and unlimited PTO
Company laptop provided

If you’re passionate about all things HR and love combining strategic advising with hands‑on problem‑solving—especially when it comes to payroll—we’d love to meet you.

Location:

Remote (Candidates must reside in IL, WI, or MI)

Compensation: $65,000–$85,000

Employment Type:

Full‑time

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