The Work

Payroll runs through the Tax Filing & Payments Team, and we're changing the way it gets done. In a conventional approach, adding more payees means also adding ever-more operators, to do more of the same manual work. We're building the opposite: a team that constantly pushes filing and payments out of people's hands and into software, piece by piece, to process payroll and file taxes at scale, reliably.

That means maintaining over a thousand unique integrations with tax agencies across every state and local jurisdiction. It also means that every person on the team is part of the pattern-finding and research motion, pinpointing the next piece of the old process to be modernized and automated. What you discover in Filing directly translates into our product roadmap, built in tight collaboration with R&D, and with AI in the loop to make the process faster along the way.

As a Tax Filing & Payments Specialist, you'll own filing and payments for multiple agencies across thousands of employers, end to end: account prep ahead of filing, original filings, monitoring failed and late payments, and filing late originals and amendments when something breaks. Along the way you'll sharpen real project-management skills and build a track record of turning "this step is annoying" into "here's what we should build instead."

No two filing periods should look the same. Each one should get easier through your own execution, the friction you notice and write up, and your ability to translate that into requirements our team can actually build against.

This isn't traditional filing and payments. You'll be managing agency integrations as R&D.

In this role, you will:

• Own jurisdictions end to end - account prep ahead of filing, original filings, monitoring failed and late payments, and late originals and amendments when things break. You'll get full visibility into the system and where the patterns that drive account maintenance live.
• File, pay, amend, and refile to exercise the system yourself, and proactively update filing specs and systems as regulations change.
• Balance tax accounts and reconcile discrepancies, and dig into root cause when an escalation gets complex - partnering across Payroll Operations, R&D, and Revenue to resolve it.
• Log friction points and translate them into requirements our team can build against. Expect to do some writing.
• Leverage AI to make your own work faster, and experiment with where it can replace a manual step entirely.
• Manage your own work: communicate proactively about deadlines, set an ambitious pace, and hold yourself to our ever-improving SLAs.

Many backgrounds could fit this role, but ideal candidates will have most or all of the following:

• 3-5 years of experience in operations or a regulated environment
• A track record of ramping into a new function or domain fast - you've picked up a new system, process, or subject area from scratch in a past role and gotten productive quickly, not just adapted to small changes within a job you already knew inside and out.
• Comfort managing your own pipeline of work: prioritizing across multiple jurisdictions and deadlines without someone assigning your day for you.
• A track record of noticing when something's broken and doing something about it. Fixing it yourself when you can, writing it up clearly when you can't.
• Genuine curiosity about AI and internal tooling. You've used AI to speed up your own work before, or you're itching to.
• Strong written communication: you'll be turning friction into requirements, so you need to write clearly enough that someone in R&D who's never filed a tax return can act on it.
• Comfort operating in a product that's still being built. You won't always have a polished tool for the job and that's part of what you're here to change.

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.