[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.ResponsibilitiesOwn filing payment operations end-to-end within your scope (e.g., assigned jurisdictions): payment setup, verification, troubleshooting, and remediation when something goes wrongDiagnose and resolve complex tax notices, determining root cause across filings, payments, agency systems, and internal workflowsDrive complex corrections and reconciliations (e.g., payment misapplies, reversals/reissues, under/overpayments), escalating thoughtfully when tradeoffs or risk are involvedPartner 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 experienceSkills4-6+ years in payroll/tax operationsDemonstrated expertise in payroll tax operations/compliance (e.g., filings/remittances, notice resolution, corrections/amendments, reconciliations), and comfort owning tax decisions/tradeoffsStartup or high-growth company backgroundStrong judgment and escalation instincts: knows when to self-serve vs. when to pull in the Tax & Compliance Manager / cross-functional partnersTrack 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 workStrong communication skills. You can translate between team-level detail and leadership-level framing, and you know which audience needs which versionA genuine learner. You'll be getting fluent in a niche domain on the job, and you find that interesting rather than uncomfortableFintech or payroll platform experience is a plus (e.g., embedded payroll, payments, or compliance tooling)BenefitsCompany-sponsored medical, dental, vision, short-term/long-term disability, and basic life insurance coverage, effective on their first day of workStock optionsFlexible PTO and sick leaveUp to 16 weeks of fully paid parental leave for new parentsFlexible return-to-work arrangements9 annual holidaysA 401(k) retirement plan$100 monthly stipend for home internet and mobile phone expensesAmple opportunities and encourage employees to attend team offsites, events, and hackathons a couple of times a yearRequired 3-day company offsiteOffices are open all weekMeals on Tuesdays and ThursdaysRegular happy hours, game nights, and other in-person eventsCompany OverviewCheck is a leading payroll infrastructure provider that allows platforms to build successful payroll businesses. It was founded in 2019, and is headquartered in New York, New York, USA, with a workforce of 51-200 employees. Its website is https://www.checkhq.com.