Operations Associate

About this role

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.

The team and role:

Check is hiring a founding cohort for a new role at Check: Operations Associate. We’re excited to bring on a new set of team members we believe have the instincts and drive to grow into different functions across the company.

You'll start on the Tax Resolution team. Tax Resolution is the detective unit of Check: when agencies send notices about payroll filings or payments, we're the ones who dig in, figure out what happened, and fix it fast. It's one of the highest-signal environments we have: you'll see how payroll and tax infrastructure actually works, what breaks, and why, and you'll be accountable for real outcomes from day one. There's no better place to develop a ground-floor understanding of the domain that Check is rebuilding.

Where you’ll go from there:

We want associates that ramp well to grow into other areas of the business. As you learn more about Check, its partners, and its operations, we think you'll be well primed to fit into different functions at Check. Imagine yourself:

- Owning an operations function - changing how our internal processes work given your knowledge of where the friction actually lives

- Becoming an expert in a domain - researching and advising on an area Check facilitates for its partners

- Jumping into R&D - writing product requirements that get shipped to help our operators

We believe that hiring a group of generalists who learn the business of Check inside and out will give us a bench of future leaders who understand both the intricacies of payroll and the needs of the partners we serve. If you’re looking for a high ownership environment, are excited for growth opportunity, and are a fast learner, we want to talk to you!

What you'll do now:

- Triage and resolve incoming tax notices, keeping partners updated with clear, timely status on each case.

- Engage directly with federal, state, and local agencies to drive resolution and pursue penalty abatement where possible.

- Investigate the root cause of every notice by researching agency rules, payroll history, and filing records — and document what you find.

- Maintain SOPs and update runbooks as you learn — your documentation will help the next person, and will show us how you think.

What we're looking for:

Any major. Any degree. Any ambition. We don't have a field or background requirement. We care about how you think, not what you studied.

The best people for this program share a few things in common:

- You want to understand things deeply. You don't just complete a task — you want to actually understand why something works the way it does. You ask the follow-up question. You read the footnotes.

- You know how to find an answer. When you hit a wall, you figure out how to get around it. You don't wait to be handed information.

- You write clearly. You can take a confusing situation and explain it in plain language to someone who doesn't have the full context.

- You catch details. The work here is consequential — small errors matter, and you're the kind of person who notices them.

- You learn fast. You can make progress in ambiguity, and pick up new concepts quickly.

A strong application looks like:

- Writing that's direct and specific. Your cover letter should sound like you actually wrote it, and should be specific to Check and this role. If you can explain clearly why you want this, that alone puts you ahead.

- Evidence you've gone deep on something. A thesis, a class project you went way beyond the assignment on, something you taught yourself because you were curious about it. Show us you know how to build real understanding, not just skim the surface.

- A problem you solved. Tell us about something you figured out, built, fixed, or improved. We want to see how you approach a hard problem.

What we offer:

Check offers company-sponsored medical, dental, vision, short-term/long-term disability, and basic life insurance, effective day one. We also offer stock options, flexible PTO and sick leave, up to 16 weeks of fully paid parental leave, flexible return-to-work, 9 annual holidays, a 401k, and a $100/month stipend for home internet and mobile.

This role is NYC-based. The expected salary range is $77,000–$87,000. Most new hires are placed near the midpoint to ensure fairness with our existing team.

We accept applications on an ongoing basis with no specified deadline.

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 a couple of times a year. All Checketeers gather in the spring for a required 3-day company offsite.

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…