Payroll Specialist

About WorkWhile
WorkWhile is on a mission to help workers earn a better living and live better lives. 83 million Americans work hourly jobs, often with unpredictable schedules that pay close to minimum wage and offer limited benefits, leading to financial instability.
WorkWhile identifies the best hourly workers and matches them with shifts that fit their skills, location, and life. Businesses get access to a quality workforce, while workers get stable income and unmatched benefits, including next day pay, free tele-health services, and financial services.
We have the audacious goal to align incentives and solve inefficiencies in the labor market, disrupting the $650 billion staffing and recruiting market. Backed by Khosla Ventures and recognized by the Inc. 5000 for 10x growth, WorkWhile is reshaping the future of work.

About the role

Join our growing People team at a time of strategic transformation. You'll deliver accurate, compliant payroll across nearly all 50 U.S. states for over 30,000 flex workers - ensuring every person is paid correctly and on time, because we know a paycheck is more than a transaction. You'll bring both precision and care to your work, acting as a specialist and advocate for the flex worker experience while helping drive process improvements and system automation that make a real difference in people's lives.

What you get to do every day

• Process full-cycle payroll for ~30,000 U.S. flex and occasional workers across nearly all 50 states, including new hires, terminations, bonuses, retroactive adjustments, off-cycle runs, and corrections.

• Support multi-state tax and regulatory compliance, including income tax, unemployment, local tax setup, state registrations, filings, remittances, and responding to notices.

• Administer garnishments, statutory deductions, and year-end filings (W-2s, etc.).

• Perform monthly and quarterly payroll reconciliations, helping to ensure payroll ties to GL and other financial systems; support internal audits and control documentation.

• Partner with HR, Finance/Accounting, and Worker Support to resolve payroll questions and deliver a seamless, positive experience for flex workers.

• Assist with benefits vendor coordination and help resolve discrepancies or escalations in a timely manner.

• Support compliance-related benefits tasks including required notices, reporting, and documentation.

• Participate in payroll system testing, process improvement initiatives, and go-live support as needed

What you bring to the role

• 2–4 years of U.S. payroll experience, preferably including multi-state operations or a high-volume hourly workforce.

• Working knowledge of U.S. payroll tax and compliance fundamentals (state/local income tax, unemployment, garnishments).

• Experience with a payroll platform (e.g., ADP, Workday, Paylocity, or similar).

• Foundational understanding of employee benefits administration and how it intersects with payroll (deductions, enrollment changes, terminations).

• Strong attention to detail and a commitment to accuracy - you understand that every paycheck matters.

• Proficiency in Excel (vlookups, pivot tables, basic reconciliations).

• Clear communicator who can work cross-functionally and support workers with empathy and professionalism.

• Comfortable working remotely and managing your own workload.

Preferred Qualifications:

• Payroll certification (FPC, CPP, or in progress).

• Exposure to multi-state payroll or large-scale hourly workforce payroll.

• Familiarity with payroll reporting or basic data tools is a plus.

• Experience with Individual Coverage HRA (ICHRA) administration - including plan setup, employee eligibility, reimbursement processing, and compliance requirements - is a strong plus.

• Familiarity with benefits platforms or ICHRA-specific vendors (e.g., Take Command, PeopleKeep, Benefitbay, or similar).

Why You'll Love It

• Be part of shaping a best-in-class payroll function - less about “keeping the lights on” and more about building the future.

• Work in a tech-forward environment where your ideas for automation, simplification and transformation will be heard and acted on.

• Opportunity to broaden scope soon into Canada - good growth potential.

• Remote flexibility plus a hub in San Francisco for connection, collaboration and culture.

Benefits & Perks

• Hybrid work culture with office hubs in SF, NY, Seattle & Toronto.

• In-person company off-sites

• Medical, dental, & vision coverage

• Flexible time off

• 401(k) with employer match

• WFH stipend to support your home office needs

Compensation & Benefits

Base salary range: $85,000-$95,000, depending on experience, location, and key skills

WorkWhile is an Equal Opportunity Employer. Women, minorities, individuals with disabilities and protected veterans are encouraged to apply. WorkWhile has a diverse, mission-driven, and supportive culture—we look for people who want to take ownership, are energized by ambiguity, and strive to make a lasting impact. If this resonates with you, we’d love to chat!