Tax Filing & Payments Associate

About the Role

Check is rebuilding payroll from the ground up, moving it off decades-old infrastructure. As the inventors of embedded payroll, we power the businesses that run payroll, not payroll itself. We're looking for someone who brings creative problem-solving, critical thinking, and grit to simplify the complexity of payroll for thousands of employers across all industries.

The Work

Payroll runs through the Tax Filing & Payments Team, and we're changing the way it gets done. Rather than adding more operators to handle more payees, we're building a team that constantly pushes filing and payments out of people's hands and into software — processing payroll and filing taxes at scale, reliably. This means maintaining over a thousand unique integrations with tax agencies across every state and local jurisdiction, and every person on the team is part of the pattern-finding and research motion, spotting the next piece of the old process that's ready to be modernized and automated. What you notice while filing feeds into the friction logs and product roadmap the team builds against, with AI in the loop to make the process faster.

As a Tax Filing & Payments Associate, you'll learn to own filing and payments for a defined set of agencies and employers, working closely with senior teammates as you build toward more independent scope. No two filing periods should look the same — each one should get a little easier as your domain knowledge builds through your own execution, the friction you notice, and your growing ability to flag it clearly for others. This isn't traditional filing and payments — you'll be learning to manage agency integrations as R&D from the ground up.

In This Role, You Will

• Take ownership of a defined set of jurisdictions with support from senior teammates — account prep ahead of filing, original filings, and monitoring failed and late payments — building toward independently handling late originals and amendments as you grow into the role.
• File and pay under established workflows to learn the system firsthand, and learn how filing specs and systems change as regulations shift.
• Help balance tax accounts and reconcile discrepancies, and learn to dig into root cause on escalations alongside more senior teammates — partnering across Payroll Operations, R&D, and Revenue.
• Log friction points as you hit them, and start building the muscle of turning what you notice into something the team can act on. Expect to do some writing.
• Leverage AI to make your own work faster and more accurate, and build the habit of reaching for it as a normal part of how you operate.
• Manage your own work within a defined scope: communicate proactively about deadlines and blockers, and build toward holding yourself to our ever-improving SLAs with less oversight over time.

Tools for the Job

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

• 1 to 2+ years of experience in operations, compliance, payroll, or a related regulated or customer-facing function — no specific degree or field of study required.
• A track record of picking up new systems, tools, or subject matter quickly, even without directly relevant past experience.
• Comfort taking ownership of a defined piece of work and asking for help early when you hit the edge of it.
• A track record of noticing when something's off and speaking up about it, even without formal authority to fix it.
• Genuine curiosity about AI and internal tooling — you've experimented with AI to speed up your own work, or you're eager to.
• Solid written communication skills; you'll be logging friction clearly enough for others to build on.
• Comfort operating in a product that's still being built, and with some ambiguity while you ramp up.

What We Offer

• Company-sponsored medical, dental, vision, short-term/long-term disability, and basic life insurance coverage, effective on first day of work.
• Stock options.
• Flexible PTO and sick leave.
• 16 weeks of fully paid parental leave for all new parents, with flexible return-to-work.
• 9 annual holidays.
• 401k retirement plan.
• $100 monthly stipend for home internet and mobile phone expenses.

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 the 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.