Tax & Payroll Operations Lead

About Check

Payroll is broken. Come fix it alongside a team that’s as passionate as you are! At Check, you'll use creative problem-solving, critical thinking, and grit to impact every business we build. We ignore conventional role boundaries in favor of the unique strengths and values each builder brings to our team, and our mission. We simplify the complex, make a real impact, and create a better future for businesses of every size.

About the role

As a Tax & Payroll 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.

In this role, you will:

• 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.

Tools for the Job

The ideal candidate will have:

• 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 have’s:

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

Travel & Office Policy

The Check team is distributed across the US. Roles can be remote, hybrid, or based in one of our offices in New York City or San Francisco. We offer ample opportunities and encourage employees to attend team offsites, events, and hackathons throughout year. All Checketeers gather in the spring for our annual 3-day company retreat.

For our in-office and hybrid employees, our offices are open all week. We provide meals on Tuesdays and Thursdays and there are regular happy hours, game nights, and other in-person events.

Remote work at Check requires the ability to perform all responsibilities without distraction or disruption, while maintaining quality, effective communication, and productivity.

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Check is proud to be an Equal Opportunity employer. We do not discriminate based on race, religion, color, national origin, sex (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender, gender identity, gender expression, transgender status, sexual stereotypes, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics. We also consider qualified applicants with criminal histories, provided they are consistent with applicable federal, state, and local laws. Check is committed to providing reasonable accommodations for candidates with disabilities in our recruiting process.

Check participates in E-Verify and will provide the federal government with Form I-9 information from all new employees to confirm that they are authorized to work in the U.S. Check does not use E-Verify to pre-screen applicants.