Tax Support Specialist

About Check

Payroll is broken. It's still running on decades-old infrastructure. We're rebuilding it. We don't run payroll ourselves we power the businesses that do. As the inventors of embedded payroll, we're redefining how people get paid and making it easier for those businesses to launch, grow, and thrive.

On our team, you'll use creative problem-solving, critical thinking, and grit to simplify the complexity of payroll for thousands of employers of every size, across all industries. We ignore conventional role boundaries in favor of the unique strengths and values each builder brings to our mission: make paying people simple. Check out our origin story!

Check is far more than just API infrastructure. We're a springboard for building and scaling payroll businesses. See how it works for our partners.

The Work

At Check, we make paying and filing taxes seamless, enabling our partners to build best-in-class payroll businesses. As a Tax Support Specialist, you own a portfolio of tax agencies from end to end meaning you're the person who knows them, handles what comes in from them, communicates on their behalf to partners, and gets resolution across the finish line.

This role will own end-to-end tax workflows. When a tax notice is received, a filing needs completed, or a partner has a tax question they can't untangle, it ends with you. You build fluency with your agencies, their quirks, their timelines, their preferred escalation paths and use that knowledge to drive fast, accurate outcomes for the partners who depend on us.

In This Role, You Will:

• Own a defined set of federal, state, and local tax agencies end-to-end, including notice resolution, correspondence, corrections, and ongoing compliance across your portfolio
• Be the direct point of contact with agencies: picking up the phone, navigating agency processes, and following through until issues are fully resolved
• Communicate directly with partners about what's happening with their notices or tax accounts translating complex agency interactions into clear, honest updates
• Balance and reconcile tax accounts within your agency portfolio, surfacing discrepancies and driving resolution
• Manage a queue of tax issues across your agencies, balancing urgency and complexity without losing track of what's open
• Recognize when patterns in your portfolio point to a larger systemic issue and bring that signal to the right people

Tools For The Job

The ideal candidate will have:

• 35 years of experience in payroll tax, tax operations, compliance, or notice resolution with meaningful exposure to both agency communication and operational/filing work
• Genuine comfort on the phone with tax agencies and in writing to partners you're clear, professional, and don't over-promise
• Experience with federal (IRS/SSA), state, and local agencies; ability to research and navigate unfamiliar ones when they come up
• Organized and methodical you can carry a portfolio of open issues across multiple agencies without things slipping
• You solve first, escalate thoughtfully, and own outcomes through to completion
• A curiosity for the edge cases; unfamiliar notice types feel like puzzles, not blockers

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 throughout year. All Checketeers gather in the spring for our annual 3-day company retreat.

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.