Tax Support Specialist

Tax Support Specialist

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 ignore conventional role boundaries in favor of the unique strengths and values each builder brings to our team, and our mission. We simplify the complex, make a real impact, and create a better future for businesses of every size.

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.

• 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

The ideal candidate will have:

• 3–5 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

The Check team is distributed across the US, with 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 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 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, game nights, etc.

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 offer stock options, flexible PTO and sick leave, 16 weeks of fully paid parental leave for all new parents, flexible return-to-work arrangements, 9 annual holidays, a 401(k) 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 location of work. Most new hires are placed near the midpoint of this range to ensure fairness with our existing team's compensation.

• The expected range in…