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 Wage Corrections 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:

• Consult with partners on how to submit payroll corrections through our product to achieve a desired end result.

• 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.

• 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

There are two backgrounds that tend to translate especially well to this work. You do not need to come from both.

You May Come From A Payroll Or Tax Operations Background

You've worked directly in payroll, payroll tax, tax compliance, or a related operational role and understand how payroll data flows into filings, payments, and employee tax forms.

We'd be excited about experience with:

• Payroll corrections, account reconciliation, and amended or corrected filings.

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

• Investigating discrepancies across wages, taxes, deductions, benefits, work locations, or historical payroll records.

• Managing complex or high-volume payroll cases against quarter-end, year-end, or filing deadlines.

Or, You May Come From A Technical Support Or Product Operations Background

You've supported a complex fintech, payroll, HR technology, or other regulated product and are comfortable investigating issues that require you to understand both the customer problem and the underlying system behavior.

We'd be excited about experience with:

• Investigating ambiguous or technically complex cases, using data and system behavior to identify root cause and determine a resolution.

• Supporting workflows where mistakes can have financial, regulatory, or customer impact.

• Working across Product, Engineering, Operations, Risk, or other technical teams to resolve issues and escalate suspected defects with strong documentation.

• Identifying recurring failure modes and improving the systems around them through better workflows, documentation, tooling, automation, or AI.

• Owning customer or partner-facing cases end to end and clearly communicating complex outcomes in writing.

Across Either Background, We're Looking For Someone Who:

• Has roughly 2–3 years of relevant experience, though we care more about the depth and relevance of your experience than an exact number of years.

• Is highly analytical and enjoys working backward from a messy problem to understand what happened.

• Is comfortable learning complex systems and developing deep domain expertise.

• Can balance accuracy, judgment, urgency, and customer impact when managing multiple cases at once.

• Is a strong written communicator who can make complicated issues understandable.

• Looks for ways to improve the process, not just resolve the individual case.

• Is comfortable using tools, including AI, to make operational work more efficient while validating outputs for accuracy.

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.