Tax Support Specialist

Job Application for Tax Support Specialist 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.

The Work

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.

Responsibilities:

• 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

Requirements:

• 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

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
• 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
• A $100 monthly stipend for home internet and mobile phone expenses