Building at Check

At Check we make paying people simple. In doing that were not just building our own business were building payroll businesses together with every one of our partners. As the inventors of embedded payroll were 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. Were a springboard for building and scaling payroll businesses.

Our Team

Payroll is broken. Come fix it alongside a team thats as passionate as you are!At Check youll 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 youre ready to roll up your sleeves and redefine payroll. Lets 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 scaleshaping 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 jurisdictionon time every timeacross hundreds of tax types nationwide. Its complex high-stakes work that sits at the intersection of regulatory expertise and operational scale.

Were looking for an experienced Payroll Tax Operations Manager to operate as a true player-coachsomeone 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 operationsaccuracy 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 Checks partners expect
• Drive process improvements to increase accuracy efficiency and scalability across tax operationsactively 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 jurisdictionsincluding 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 executionstepping 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 startuppayroll or tax experience is a strong plus. Youve built systems and teams not just managed steady-state operations
• Familiarity with multi-jurisdiction payroll tax filingfederal state and local including refiles amendments and notice resolutionis 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 operationsyoure 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 candidates experience qualifications and work location:

• The expected range in San Francisco NYC LA and Seattle is between $165000 and $181500.
• The expected range for all other locations is between $140500 and $154550.

#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.

Checkparticipates inE-Verifyand 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.Checkdoes not useE-Verifyto pre-screen applicants.