Tax Quality Lead

The Work

Payroll tax requires precision across hundreds of jurisdictions, each with its own portal, forms, deadlines, and rules, and those requirements change continually. At Check, ensuring that every filing is accurate for our partners and their employers is central to what we do. The Tax Quality & Research team is responsible for that standard. On our team, surface area and accountability for outcomes is shared. Our sense of ownership is deep but not territorial, and we approach challenges collaboratively.

As a Tax Quality Lead, you will be responsible for compliance, accuracy, timeliness, and reliability across the full filing lifecycle. You will research what each agency requires, translate those requirements into system configurations, and test them before they go live. Once filings are in motion, you will validate results, investigate any discrepancies to their root causes, and feed what you learn back into how we research and build moving forward.

In this role you’ll not only ensure best-in-class service delivery for our partners, but also help shape how the work gets done. You’ll partner with Engineering and Product to accelerate our processes with AI and improved tooling, and you will be an important voice in evolving the infrastructure at the core of our product. Over time you’ll take on larger initiatives that expand our tax engine capabilities and improve our validation tooling.

In This Role, You Will

• Contribute to initiatives and workstreams that that improve Check’s on-time filing rate, tax form accuracy, and notice rate.
• Strengthen how research is organized, documented, and shared across teams.
• Research agency requirements and translate them into clear, documented internal and external guidance.
• Identify and act on opportunities to automate recurring work, eliminate manual processes, and improve the tools the team relies on.
• Build new tax configurations and test them for accuracy before they go live.
• Validate results on an ongoing basis to identify issues early.
• Investigate discrepancies to root cause and implement lasting solutions.
• Communicate requirements to Engineering and Product in a clear and actionable format.

The Ideal Candidate Will Have

• Hands-on payroll tax experience. 6+ years working on filings, notices, amendments, agency interactions, or tax configuration.
• A track record of improving how work gets done. You can describe a process you inherited, what you changed, and how you measured the result.
• Experience partnering with Engineering and Product teams. You’ve written a request or specification that resulted in something new and impactful being built.
• The ability to learn new systems independently. You have mastered a new technical system or tool on your own.
• Practical experience using AI in your work. You can share a concrete example, or you have a clear interest and a plan to begin.
• Comfort working with data. You use it to identify patterns and confirm that improvements are effective.

Nice to Have

• Experience with native tax calculation and filing systems, or form-building tools.
• Experience in B2B fintech, payments, or another regulated or technically complex domain.

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.