[Remote] Tax & Compliance 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, encouraging innovative problem-solving among its team. The Tax & Compliance Operations Lead will be responsible for overseeing tax payment operations, diagnosing complex tax notices, and driving improvements in workflows to ensure accuracy and efficiency in tax-related processes.
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
- Required 3-day company offsite
- Offices are open all week
- Meals on Tuesdays and Thursdays
- Regular happy hours, game nights, and other in-person events
Company Overview