Tax & Compliance Operations Specialist

Building at Check

At Check, we make paying people simple. In doing that, we’re not just building our own business— we’re building payroll businesses together with every one of our partners. As the inventors of embedded payroll, we’re redefining how people get paid and making it easier for payroll businesses to launch, grow, and thrive. Check out the full story | Tune in.

Check is far more than just API infrastructure. We’re a springboard for building and scaling payroll businesses.

Our Team

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 view problems to solve and jobs to be done as opportunities to contribute to the solution; we ignore conventional role boundaries in favor of the unique strengths and value each builder brings to our team and to our mission.

Join us if you’re ready to roll up your sleeves and redefine payroll. Let’s simplify the complex, make a real impact, and create a better future for businesses of every size.

The Work

At Check, we make paying and filing taxes seamless, enabling our partners to build best-in-class payroll businesses. The Tax Operations team sits at the core of this mission, turning complex tax workflows into reliable, repeatable processes that power partner success.

As a Tax & Compliance Operations Specialist, you will contribute to operational excellence by executing and optimizing critical tax functions. You’ll focus on balancing tax accounts, managing corrections and amendments, supporting tax compliance, and streamlining internal workflows to ensure accuracy, efficiency, and scalability.

This role is for someone who thrives on operational precision, solves problems with a hands-on approach, and is energized by making complex systems work better.

In this role, you will:

• Ensure tax compliance by executing accurate filings and remittances and proactively updating filing specifications and systems in response to regulatory changes.
• Manage corrections and amend tax returns as needed, working within established workflows and partnering across teams to resolve discrepancies.
• Balance tax accounts and reconcile discrepancies to support accurate and timely tax reporting.
• Assist in resolving complex tax escalations through root cause analysis and cross-functional collaboration.
• Identify opportunities to simplify and optimize tax operations, proposing process improvements and leveraging data for continuous refinement.
• Partner closely with Payroll Operations, R&D, and Revenue teams to streamline tax workflows and contribute to initiatives that enhance compliance and partner satisfaction.

Tools for the Job

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

• 3–5 years of experience in tax operations, compliance, payroll, or related functions, with strong knowledge of tax filing and remittance processes.
• Experience handling corrections, amendments, and account reconciliations in a payroll or tax context.
• Familiarity with compliance requirements and best practices in a regulated operational environment.
• Demonstrated ability to identify process improvements and implement operational solutions at scale.
• Strong problem-solving, organizational, and communication skills.
• Comfort working cross-functionally to support product and partner outcomes.
• A partner-first mindset with a strong focus on quality, efficiency, and service.

Travel and Office Policy: We build best when we come together on level ground.

The Check team is distributed across the US, and we have offices in New York City and San Francisco. While we embrace remote work, time together in person is where we do our best work. We offer ample opportunities and encourage employees to attend team offsites, events, and hackathons a couple of times a year! We expect all employees to attend our annual 3-day company retreat in the spring. 

For our in-office and hybrid employees, our offices are open all week. We provide meals on Tuesdays and Thursdays and the team hosts regular happy hours, game nights, etc.

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.

• The expected range in San Francisco, New York, Los Angeles, and Seattle is between $90,000 and $99,000.
• The expected range for all other locations is between $76,500 and $84,150.

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

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, consistent with applicable federal, state and local law. 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.