The posting
ABOUT CHECK
Payroll is broken. It's still running on decades-old infrastructure. We're rebuilding it.
We don't run payroll ourselves — we power the businesses that do. As the inventors of embedded payroll, we're redefining how people get paid and making it easier for those businesses to launch, grow, and thrive.
On our team, you'll use creative problem-solving, critical thinking, and grit to simplify the complexity of payroll for thousands of employers of every size, across all industries. We ignore conventional role boundaries in favor of the unique strengths and values each builder brings to our mission: make paying people simple. Check out our origin story! https://app.notion.com/p/checkhq/The-Generalist-Check-Solving-the-150-Billion-Payroll-Problem-3b24274a2e75804e9141cfac60476d25?source=copy_link
Check is far more than just API infrastructure. We’re a springboard for building and scaling payroll businesses. See how it works for our partners. https://www.checkhq.com/partners
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, 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 along the way.
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: account prep ahead of filing, original filings, and monitoring failed and late payments, with growing exposure to late originals and amendments as things break. Along the way you'll build real execution skills and start turning "this step is annoying" into a clear writeup someone else can act on.
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
For full-time employees, Check offers company-sponsored medical, dental, vision, short-term/long-term disability, and basic life insurance coverage, effective on their first day of work. We also provide stock options, flexible PTO and sick leave, 16 weeks of fully paid parental leave for all new parents, flexible return-to-work, 9 annual holidays, a 401k retirement plan, and a $100 monthly stipend for home internet and mobile phone expenses.
The actual annual salary for this role depends on each candidate's experience, qualifications, and work location. Most new hires are placed near the midpoint of this range to ensure fairness with our existing team's compensation.
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.
