Tax Resolution Specialist

Check • New York, NY

98d • $78,500 - $102,500

About The Position

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 is far more than just API infrastructure. We’re a springboard for building and scaling payroll businesses. 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.

Requirements

• 3–5 years of experience in payroll tax compliance, tax notice resolution, or payroll operations.
• Solid understanding of payroll tax regulations across federal, state, and local agencies.
• Clear, confident communication skills with the ability to translate complex tax issues into plain language for partners.
• Proven track record of handling sensitive employer information with care and discretion.
• Familiarity with payroll systems, tax filing platforms, or case management tools.
• Highly organized, detail-oriented, and comfortable managing multiple priorities in a fast-paced environment.

Responsibilities

• Triage and resolve tax notice queues by priority, keeping partners informed with clear, timely updates.
• Engage directly with federal, state, and local agencies to investigate root causes, drive resolution, and pursue penalty abatements.
• Surface complex or systemic issues to product, engineering, and compliance for deeper investigation and long-term fixes.
• Spot trends across notices and recommend improvements that reduce risk and speed up resolution.
• Maintain and refine SOPs to capture best practices for agency outreach and notice handling.
• Collaborate with Payroll Ops, R&D, and Revenue to streamline tax workflows and strengthen partner trust in Check.

Benefits

• 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.
• 10 annual holidays.
• 401k retirement plan.
• $100 monthly stipend for home internet and mobile phone expenses.

What This Job Offers

• Job Type: Full-time
• Number of Employees: 101-250 employees