Payroll Support Specialist

About Check

Payroll is broken. It's still running on decades-old infrastructure. We're rebuilding it.

We don't run payroll ourselves — we power the businesses that do. As the inventors of embedded payroll, we're redefining how people get paid and making it easier for those businesses to launch, grow, and thrive.

On our team, you'll use creative problem-solving, critical thinking, and grit to simplify the complexity of payroll for thousands of employers of every size, across all industries. We ignore conventional role boundaries in favor of the unique strengths and values each builder brings to our mission: make paying people simple. Check out our origin story!

Check is far more than just API infrastructure. We’re a springboard for building and scaling payroll businesses. See how it works for our partners.

The team and role

The Partner Support Team resolves payroll and payroll tax discrepancies after they occur. When wages are recorded incorrectly, an employee is set up in the wrong jurisdiction, a benefit or deduction is applied in error, or data from a prior provider is incomplete, the impact can extend across multiple pay periods, quarters, and tax jurisdictions — frequently including filings that have already been submitted and paid.

As a Payroll Specialist on the Support team, you will own these cases end to end: investigating the underlying issue, correcting historical payroll records, determining the downstream filing and financial impact, and communicating the outcome to our partners. Corrections you complete are what drive amended filings, corrected employee forms, and adjustments to funds owed or refunded, so the role carries significant responsibility for accuracy. Because most corrections involve prior quarters, the work is analytical and consequential, requiring judgment on what changed, what must be amended, and how to explain both clearly.

This role calls for payroll tax depth, strong investigative instincts, and precise written communication. You will work closely with Tax Operations, Payroll Operations, Engineering, Product, Risk, and Revenue, and will build deep expertise in multi-jurisdiction payroll tax and in the systems that support it at scale.

In this role, you will:

• Investigate payroll and payroll tax discrepancies to identify root cause and determine the full scope of impact across employees, pay periods, quarters, and jurisdictions.

• Correct historical payroll records, including wages, taxes, benefits, deductions, exemptions, and work locations, and verify the accuracy of the corrected results.

• Determine which previously submitted filings are affected by a correction and identify the amendments required by period, jurisdiction, and form, providing the filing team with complete and accurate documentation.

• Determine when corrected employee and contractor tax forms, such as W-2C and 1099 corrections, are required, and confirm the corrected figures are accurate before they are issued.

• Reconcile tax accounts by balancing calculated, collected, and filed amounts, and identify the resulting tax due, refund, or credit.

• Determine the financial impact of each correction and initiate the appropriate collection or refund, partnering with internal teams to see it through to completion.

• Assess materiality and filing obligations to determine the appropriate scope of each correction, and document the supporting rationale.

• Communicate correction outcomes, resulting filing changes, tax impact, and expected timelines to partners through clear, accurate, and timely written updates.

• Partner with Tax Operations, Payroll Operations, Engineering, Product, and Risk to resolve complex cases and escalate suspected product defects with complete context.

• Manage a high volume of concurrent cases against filing deadlines and service level commitments, prioritizing by risk and impact.

• Identify recurring root causes and recommend process, documentation, automation, and product improvements that reduce correction volume.

Many backgrounds could fit this role, but ideal candidates will have some or all of the following:

• 3–4 years of experience in payroll operations, payroll tax, tax compliance, or a client-facing role supporting a payroll, HR technology, or fintech product.

• Hands-on experience with payroll corrections, account reconciliation, and the amendment process, or comparable experience correcting regulated submissions, including fluency with corrected and amended tax forms.

• Working knowledge of multi-jurisdiction payroll tax, including federal employment taxes, state income tax and unemployment insurance, paid leave and disability programs, annual reconciliations, and local taxes.

• Demonstrated success analyzing data to investigate issues and identify root causes along with resolutions, including advanced spreadsheet proficiency; SQL experience a plus.

• A demonstrated ability to identify process improvements and implement operational solutions at scale, including the use of AI tooling to automate workflows while validating for accuracy.

• Experience with ticketing and/or case management systems, especially Zendesk.

• Availability to support Check's operating elevated workload during quarter-end and year-end filing periods, and to attend our annual 3-day company offsite each spring.

Travel & Office Policy

The Check team is distributed across the US. Roles can be remote, hybrid, or based in one of our offices in New York City or San Francisco. We offer ample opportunities and encourage employees to attend team offsites, events, and hackathons throughout year. All Checketeers gather in the spring for our annual 3-day company retreat.

For our in-office and hybrid employees, our offices are open all week. We provide meals on Tuesdays and Thursdays and there are regular happy hours, game nights, and other in-person events.

Remote work at Check requires the ability to perform all responsibilities without distraction or disruption, while maintaining quality, effective communication, and productivity.

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Check is proud to be an Equal Opportunity employer. We do not discriminate based on race, religion, color, national origin, sex (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender, gender identity, gender expression, transgender status, sexual stereotypes, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics. We also consider qualified applicants with criminal histories, provided they are consistent with applicable federal, state, and local laws. Check is committed to providing reasonable accommodations for candidates with disabilities in our recruiting process.

Check participates in E-Verify and will provide the federal government with Form I-9 information from all new employees to confirm that they are authorized to work in the U.S. Check does not use E-Verify to pre-screen applicants.