Payroll & Tax Support Associate

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 The Tax Support team 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. In this role you'll be embedded on the Tax Support team from day one - real notices, real agency interactions, real consequences for our partners. You'll be matched with a senior team member who'll work alongside you and push you to ramp fast. You'll develop a working understanding of how some of the most foundational infrastructure in business operates: payroll systems, tax regulation, and the compliance machinery that connects employers to government agencies. You'll be doing it at a company that's rebuilding how that infrastructure works, which means you're not just learning a domain, you're learning how fintech companies create leverage at the intersection of software and financial systems. In the process, you'll get firsthand experience navigating some of the most fundamental systems that keep businesses running: how companies pay their people, how tax obligations flow between employers and government agencies, and what happens when something breaks in that process. That's deeply transferable knowledge, whether you stay in payroll, move into compliance/policy/operations, or go somewhere else entirely. Understanding how money moves and how government regulates it is useful almost everywhere. This is a role is for NYC-based candidates only, as the in-person time in the office will help accelerate the ramp and your understanding about payroll and taxes. What you'll do 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. What we're looking for This role is built with a specific belief: the best person for this role doesn't necessarily have a tax background already — and that's fine. What matters is that you're genuinely curious about how things work, motivated to build real expertise in an industry, and want to do work that makes an impact. Any major. Any degree. Any ambition. We don't have a field requirement or a GPA cutoff. We care about how you think, not what you studied. We'll teach you how the payroll tax system works, how we work with federal and state tax agencies, and how to read and resolve a notice. What we can't teach is the instinct to dig into a hard problem. You'll fit in here if: 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're okay not knowing things yet, but 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. Show us something you've genuinely dug into. A thesis, a class project you went way beyond the assignment on, something you taught yourself because you were curious about it. We want to see that you know how to build real understanding of something, not just skim the surface. A problem you solved. Tell us about something you figured out, built, fixed, or improved, be it a class project, a job, community problem, a research paper, anything. We want to see the instinct to identify and solve a problem in action, and learn how you approached it. 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, up to 16 weeks of fully paid parental leave for 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. This opportunity is open to New York-based candidates only at this time. In New York, the expected salary for the role is between $77,000 - $87,000 per year. 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. 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. -- 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.