Payroll & Tax Support Associate
About The Position
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.
Requirements
- Genuinely curious about how things work.
- Motivated to build real expertise in an industry.
- Want to do work that makes an impact.
- Ability to understand things deeply and ask follow-up questions.
- Ability to find an answer when hitting a wall.
- Ability to write clearly and explain confusing situations in plain language.
- Attention to detail; noticing small errors.
- Ability to be okay not knowing things yet, but learn fast.
- Ability to make progress in ambiguity and pick up new concepts quickly.
Nice To Haves
- Writing that's direct and specific.
- Cover letter that sounds like you actually wrote it and is specific to Check and this role.
- Evidence you've gone deep on something (thesis, class project, self-taught skill).
- A problem you solved (class project, job, community problem, research paper).
Responsibilities
- 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.
Benefits
- Company-sponsored medical, dental, vision, short-term/long-term disability, and basic life insurance coverage, effective on their first day of work.
- 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
- 401k retirement plan
- $100 monthly stipend for home internet and mobile phone expenses.
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What This Job Offers
Job Type
Full-time
Career Level
Entry Level
Education Level
No Education Listed
