Tax & Compliance Operations Lead

Check Technologies

11d • $94,000 - $122,000 • Hybrid

About The Position

As a Tax & Compliance Operations Lead focused on filing payments and notice diagnosis, you will be a key operator in the tax lifecycle—ensuring payments are accurate and timely, resolving complex agency notices, and applying strong judgment to ambiguous tax scenarios. You’ll bring a big-picture understanding of how filings, remittances, and downstream corrections connect, and you’ll help drive improvements that make our workflows more reliable and scalable.

Requirements

• 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.

Nice To Haves

• Fintech or payroll platform experience is a plus (e.g., embedded payroll, payments, or compliance tooling).

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.

Benefits

• company-sponsored medical, dental, vision, short-term/long-term disability, and basic life insurance coverage
• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed