Job Description

About Bookkeeper360
Bookkeeper360 is a fintech company helping small businesses manage their finances through cloud-based accounting, payroll, tax, and advisory services, powered by AI-driven insights. Since 2012, we've been a trusted partner to thousands of business owners and have earned recognition from NerdWallet, Forbes, and Entrepreneur as a top bookkeeping solution.

We're proud to be named one of Accounting Today's 2024 Best Firms to Work For and a Fastest Growing Company by Inc. 5000 . With a 4.8-star Google rating from 1,000+ clients, we're growing fast and expanding our team to meet demand.

Want to learn how it all started? Check out ( story of our founder and CEO (

About the Role

As a Senior Payroll Specialist, you'll work with a diverse portfolio of client accounts, supporting 40–60 small businesses across multiple industries and states. You'll serve as a trusted payroll expert, handling everything from processing and registrations to troubleshooting and platform migrations, ensuring every client's payroll is accurate, compliant, and on time.

You'll collaborate closely with our Payroll & HRIS Manager to deliver exceptional client experiences while identifying process improvements that scale.

What You'll Do: 

Payroll Processing & Compliance

• Process and review multi-state payrolls (weekly, biweekly, semimonthly, and monthly) for a portfolio of 40-60 clients using Gusto, ADP, Paychex, and Justworks, ensuring accuracy, timeliness, and compliance with all deadlines.
• Lead or assist with migrating clients between payroll systems, ensuring accurate data transfers, beginning balances, and compliance alignment.
• Set up and maintain earnings, deductions, reimbursements, and benefits (401(k), HSAs, FSAs, stipends, garnishments).
• Ensure compliance with minimum wage, overtime, and final pay laws across all 50 states.
• Reconcile payroll journals, tax liabilities, and GL postings with accounting teams, ensuring accuracy and timely completion each cycle.
• Identify and correct discrepancies quickly to prevent payroll delays, escalating complex situations when appropriate.

Tax Registrations, Filings & Issue Resolution

• Coordinate state withholding and unemployment insurance registrations for new employers and handle updates or closures as needed.
• Troubleshoot federal and state payroll tax filings (941, 940, CA DE-9/DE-9C, NY-45, etc.) when filings fail or require intervention.
• Research and assist with amended or prior-period filings (941-X, state amendments, zero filings) under the guidance of the Payroll & HRIS Manager.
• Respond to payroll tax notices or discrepancies, collaborating with agencies or software providers to resolve issues efficiently.
• Maintain an organized database of state registration details, agency credentials, and filing requirements to support departmental consistency.

Client Communication & Collaboration

• Serve as a primary payroll contact for a large client base, providing clear, timely, and professional communication.
• Work closely with multiple clients simultaneously, ensuring accurate and on-schedule payroll delivery across all accounts.
• Coordinate payroll system transitions by supporting clients through onboarding, data collection, and platform setup.
• Provide expert, approachable guidance on payroll tax, benefits, compliance, and best practices to small business owners and internal teams.
• Collaborate cross-functionally with bookkeeping, tax, and HRIS teams to ensure seamless service delivery.
• Contribute to departmental SOPs, templates, and process improvements to enhance efficiency and scalability.

How to Be Successful in This Role:

• You thrive in complexity and find satisfaction in accuracy.
• You're the go-to person for troubleshooting tricky payroll tax or state registration issues.
• You're tech-savvy, resourceful, and proactive in communicating with clients.
• You have a “no drama, just solutions” approach to challenges.

What Gets You to the Top of the List:

• 5+ years of payroll experience, including multi-state processing and client-facing interaction.
• Hands-on experience registering and maintaining state withholding and unemployment accounts.
• Solid understanding of payroll tax filings (federal and state) and ability to identify and resolve filing discrepancies.
• Working knowledge of labor laws (final pay, overtime, exempt vs. nonexempt, wage theft prevention, etc.).
• Familiarity with 401(k) and benefit deduction structures, including pre-tax and post-tax setups.
• Proven ability to manage complex client relationships with professionalism and confidence.
• Adaptability to work across multiple platforms (Gusto, ADP, Paychex, Justworks, Rippling, or similar).
• Strong attention to detail and commitment to compliance.
• Comfort in a remote, fast-paced, client-facing environment.

Bonus Points For

• Prior experience with quarterly payroll corrections (941-X, state amendments).
• Knowledge of Secretary of State registration or business entity compliance (not required but a plus).
• Experience in public accounting or client advisory environments
• Certified Payroll Professional (CPP) or FPC certification.

What You Can Expect as a Team Member

• Salary range from $70,000-$90,000/year + performance bonus
• Comprehensive benefits package including medical, dental, and vision
• 401K with employer match after the first year
• Paid parental leave for all parents (biological, adoptive, and foster)
• Fully remote work environment
• Unlimited PTO after your first year
• Company-paid holidays
• Team-building events and virtual activities
• Career development and internal promotion opportunities

At Bookkeeper360, we are committed to hiring diverse talent of different backgrounds and as such, it is important to us to provide an inclusive work environment for all. We do not discriminate on the basis of race, gender identity, age, religion, sexual orientation, veteran or disability status, or any other protected class. As an equal opportunity employer, we encourage and welcome people of all backgrounds to apply.

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