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CheckCheckNew York, NY

Tax & Compliance Operations Lead

Lead tax filing payment operations and resolve complex compliance notices for a payroll platform. Requires 4-6+ years of payroll tax operations experience in a startup environment.

94k – 122k
Remote4+ YOEFinance & Accounting

About the role

Responsibilities

  • Own filing payment operations end-to-end within assigned jurisdictions: payment setup, verification, troubleshooting, and remediation
  • Diagnose and resolve complex tax notices, determining root cause across filings, payments, agency systems, and internal workflows
  • Drive complex corrections and reconciliations (e.g., payment misapplies, reversals/reissues, under/overpayments)
  • Partner with R&D / Product and cross-functional ops teams to inform system behavior and prevent repeat issues
  • Identify patterns across payments + notices and propose improvements that reduce risk, shorten resolution times, and improve partner experience

Requirements

  • 4-6+ years in payroll/tax operations
  • Demonstrated expertise in payroll tax operations/compliance (filings/remittances, notice resolution, corrections/amendments, reconciliations)
  • Startup or high-growth company background
  • Strong judgment and escalation instincts
  • Track record of process improvement
  • Startup instincts: writes the runbook before one exists, creates lightweight controls/visibility, turns recurring issues into scalable fixes
  • AI-forward mindset: uses AI tools to move faster while validating for correctness in regulated work
  • Strong communication skills

Nice to Haves

  • Fintech or payroll platform experience (embedded payroll, payments, or compliance tooling)

Skills

Payroll Tax OperationsTax ComplianceFiling And Remittance ManagementNotice ResolutionPayment ReconciliationProcess ImprovementCross-Functional CollaborationRegulatory Compliance

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