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Check is rebuilding payroll infrastructure by powering embedded payroll for thousands of businesses. The Tax Filing & Payments Team is responsible for maintaining over 1,000 integrations with tax agencies across every state and local jurisdiction, automating manual processes piece by piece.
As a Tax Filing & Payments Specialist, you will own end-to-end filing and payments for multiple agencies across thousands of employers. Your responsibilities include account preparation ahead of filing, original filings, monitoring failed and late payments, filing late originals and amendments when issues arise, and reconciling tax account discrepancies. You'll exercise the system yourself by filing, paying, amending, and refiling to identify friction points and translate them into product requirements for the R&D team.
You'll balance tax accounts, dig into root causes of complex escalations, and partner across Payroll Operations, R&D, and Revenue to resolve issues. A key part of the role is documenting friction points and writing clear requirements that engineers can act on. You'll leverage AI tools to accelerate your own work and experiment with automation opportunities. The role requires self-directed work management: communicating proactively about deadlines, setting an ambitious pace, and maintaining improving SLAs.
Ideal candidates have 3–5 years in operations or regulated environments, a track record of ramping into new domains quickly, comfort managing their own work pipeline across multiple jurisdictions and deadlines, and a history of identifying and fixing broken processes. Strong written communication is essential, as you'll translate operational friction into technical requirements. Genuine curiosity about AI and internal tooling is valued. You should be comfortable operating in a product still being built, where polished tools may not yet exist—that's part of what you're here to change.
