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

This is a rare opportunity to build and lead a tax operations function at scale—shaping the systems, team, and standards that will define how an entire industry gets payroll right.

Tax Operations at Check is the backbone of compliance and accuracy for the tens of thousands of businesses we serve. Our team ensures that every payroll dollar flows to the right jurisdiction—on time, every time—across hundreds of tax types nationwide. It's complex, high-stakes work that sits at the intersection of regulatory expertise and operational scale.

We're looking for an experienced Tax Manager to operate as a true player-coach—someone who can lead the team while staying close to the work. This role owns end-to-end tax operations across a blended team of FTEs and contingent workers, with a strong emphasis on people management, execution quality, and operational ownership. The right candidate will be equally comfortable setting direction, coaching team members, and rolling up their sleeves to handle complex tax work when needed.

In this role, you will:

• Build and lead a high-performing team of tax professionals (FTEs and contractors)—owning team outcomes, setting clear accountability standards, and developing talent through coaching, performance management, and strategic capacity planning
• Set and enforce a high quality bar across all tax operations—accuracy, timeliness, and thoroughness are non-negotiable, and you hold the team to that standard
• Own the partner experience for tax operations: filings, notices, and escalations handled with urgency and transparency, with every interaction reflecting the standard Check's partners expect
• Drive process improvements to increase accuracy, efficiency, and scalability across tax operations—actively leveraging AI tools across all aspects of the work, from research and analysis to drafting, decision-making, and beyond
• Partner cross-functionally with Engineering, Product, and Revenue teams to surface and resolve systemic issues
• Own accountability for end-to-end tax operations across jurisdictions—including batch filings, refiles, amendments, tax preparation, and notice management and resolution
• Act as the primary escalation point for complex or high-risk tax issues, applying deep expertise to resolve edge cases and minimize risk exposure
• Balance strategic leadership with hands-on execution—stepping in directly where needed while ensuring the team operates effectively at scale

Tools for the job

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

• 7+ years leading operations or compliance teams in technology, fintech, or a rapidly scaling startup—payroll or tax experience is a strong plus. You've built systems and teams, not just managed steady-state operations
• Familiarity with multi-jurisdiction payroll tax filing—federal, state, and local, including refiles, amendments, and notice resolution—is a strong plus; deep expertise is welcome but not required
• Demonstrated ability to lead both FTEs and contractors in a fast-moving, high-volume operational environment
• A track record of driving process improvement and building scalable operations—you're energized by ambiguity, comfortable operating without a playbook, and at your best when building in a fast-moving, rapidly changing environment rather than maintaining the status quo
• Strong judgment in escalation handling: you know when to roll up your sleeves and when to delegate
• Experience with payroll platforms or tax software; comfort with technical tooling and data is a plus
• Curiosity about and comfort using AI tools to improve workflows, identify patterns, and drive operational efficiency

We build best when we come together on level ground.

Travel and Office Policy

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

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 stock options, flexible PTO and sick leave, up to16 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. We also provide high-quality medical, dental, vision, short-term/long-term disability, and basic life insurance coverage, effective on your first day of work.

At Check, transparency and fairness in compensation are our top priorities: our compensation bands are visible to all employees across all roles. The actual annual salary for this role is dependent on each candidate's experience, qualifications, and work location:

• The expected range in San Francisco, NYC, LA, and Seattle is between $165,000 and $181,500.
• The expected range for all other locations is between $140,500 and $154,550.

#li-remote

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

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.