Senior Payroll Analyst

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 telehealth 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

WorkWhile is looking for an experienced Senior Payroll Analyst. 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, and be a core contributor as we build out and improve our product for our W2 platform users. As we build out our in-house stack and modernize payroll operations end-to-end, you’ll act as both a specialist and a change-agent — ensuring day-to-day excellence and helping drive process improvements, system automation, and controls maturity.

What you get to do every day

• Execute 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.

• Participate in system design, requirement gathering, vendor assessments, testing and go-live support.

• Support maintenance of tax/regulatory compliance: multi-state tax set-ups (income tax, unemployment), local tax nexus, state registrations, filings, remittances, and notices.

• Administer garnishments, statutory deductions, and year-end filings

• Perform monthly and quarterly reconciliations tying payroll to GL and other financial systems; support internal audits and documentation of controls.

• Serve as the subject-matter expert for our in-house payroll system and any related transformation (data migration, automation of reports, vendor transitions).

Partner cross-functionally with HR, Finance/Accounting, Worker Support and external providers to deliver seamless payroll experience and continuous improvement.

What you bring to the role

• 5+ years of U.S. payroll experience, ideally covering multi-state operations and servicing a large hourly front-line employee base.

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

• Experience with payroll systems and comfort working in a transformation setting (system upgrades, migrations, process redesign)

• Excellent analytical skills—Excel proficiency (lookups, pivots, reconciliations), good data-QA instincts. Familiar with AI products and eager to use AI to increase leverage and speed.

• Experience utilizing API integrations to manage large-scale data imports and exports for payroll migration/automation

• Comfort working remotely/hybrid, self-managing, collaborating across functions and time zones.

• Strong communication skills: able to liaise with internal stakeholders and external providers.

Preferred Qualifications:

• Payroll certification (CPP or equivalent) or in progress.

• Experience with reporting tools or system build (SQL, custom payroll modules) is a plus.

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

• Remote work culture with opportunities for coworking in SF, NY & Toronto

• In-person company offsites

• Medical, dental, & vision coverage

• Flexible time off

• 401(k) with employer match

• WFH stipend to support your home office needs

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!