[Remote] Tax & Payroll Operations Lead

Note: The job is a remote job and is open to candidates in USA. Check is a company focused on revolutionizing payroll processes. As a Tax & Payroll Operations Lead, you will manage filing payments and resolve complex tax scenarios, ensuring accuracy and compliance while driving operational improvements.

Responsibilities

• Own filing payment operations end-to-end within your scope (e.g., assigned jurisdictions): payment setup, verification, troubleshooting, and remediation when something goes wrong
• 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), escalating thoughtfully when tradeoffs or risk are involved
• Partner with R&D / Product and cross-functional ops teams to inform system behavior and prevent repeat issues (better tooling, validations, automation, and documentation)
• Identify patterns across payments + notices and propose improvements that reduce risk, shorten resolution times, and improve partner experience

Skills

• 4-6+ years in payroll/tax operations
• Demonstrated expertise in payroll tax operations/compliance (e.g., filings/remittances, notice resolution, corrections/amendments, reconciliations), and comfort owning tax decisions/tradeoffs
• Startup or high-growth company background
• Strong judgment and escalation instincts: knows when to self-serve vs. when to pull in the Tax & Compliance Manager / cross-functional partners
• Track record of process improvement: can spot patterns and help drive changes that reduce recurrence (tooling, documentation, controls)
• Startup instincts in practice: writes the runbook before one exists, creates lightweight controls/visibility, and turns recurring issues into a scalable fix (not just a workaround)
• AI-forward mindset: uses AI tools to move faster (analysis, drafting, pattern recognition) while validating for correctness in regulated work
• Strong communication skills. You can translate between team-level detail and leadership-level framing, and you know which audience needs which version
• A genuine learner. You'll be getting fluent in a niche domain on the job, and you find that interesting rather than uncomfortable
• Fintech or payroll platform experience is a plus (e.g., embedded payroll, payments, or compliance tooling)

Benefits

• Company-sponsored medical, dental, vision, short-term/long-term disability, and basic life insurance coverage, effective on their first day of work
• Stock options
• Flexible PTO and sick leave
• Up to 16 weeks of fully paid parental leave for new parents
• Flexible return-to-work arrangements
• 9 annual holidays
• A 401(k) retirement plan
• $100 monthly stipend for home internet and mobile phone expenses
• Ample opportunities and encourage employees to attend team offsites, events, and hackathons a couple of times a year
• All Checketeers gather in the spring for a required 3-day company offsite
• Meals on Tuesdays and Thursdays
• Regular happy hours, game nights, and other in-person events

Company Overview