[Remote] Tax Resolution Specialist at Check

New York, New York, United States

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Not SpecifiedCompensation

Junior (1 to 2 years)Experience Level

Full TimeJob Type

UnknownVisa

Payroll, FinTechIndustries

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

Skills

Key technologies and capabilities for this role

Tax ResolutionPayroll Tax ComplianceIssue InvestigationAgency CommunicationTriageQueue ManagementPartner UpdatesRegulatory Notices

Questions & Answers

Common questions about this position

What experience is required for the Tax Resolution Specialist role?

Ideal candidates have 3–5 years of experience in payroll tax compliance, tax notice resolution, or payroll operations, along with a solid understanding of payroll tax regulations across federal, state, and local agencies.

What communication skills are needed for this position?

The role requires clear, confident communication skills with the ability to translate complex tax issues into plain language for partners.

What is the company culture like at Check?

Check fosters a passionate team environment focused on creative problem-solving, critical thinking, and grit, where team members ignore conventional role boundaries to leverage unique strengths and contribute to redefining payroll.

What is the salary or compensation for this role?

This information is not specified in the job description.

What makes a strong candidate for the Tax Resolution Specialist position?

Strong candidates have 3–5 years in payroll tax compliance or related fields, deep knowledge of tax regulations, and excellent communication skills, with many backgrounds potentially fitting the role.

Check

Provides embedded payroll services for software platforms

About Check

CheckHQ offers embedded payroll services tailored for software platforms in the fintech sector. Their primary product is a payroll system that can be integrated into existing software, allowing businesses to create and manage their own payroll services. This integration helps platforms like Homebase and Housecall Pro enhance their offerings, leading to increased revenue and improved customer retention. Unlike traditional payroll providers, CheckHQ focuses on partnerships, supplying the necessary back-end technology while the partner platforms handle the customer-facing aspects. This approach enables quicker market entry and scalability, making it easier for platforms to add payroll services without significant upfront investment. The goal of CheckHQ is to empower software platforms to diversify their services and boost customer engagement through effective payroll solutions.

New York City, New YorkHeadquarters

2019Year Founded

$116.7MTotal Funding

SERIES_CCompany Stage

Enterprise Software, FintechIndustries

51-200Employees

Benefits

Home office stipend: $1k stipend for your home office setup, and $100 per month for internet and cell.

PTO & sick leave: Recharge and stay healthy with flexible PTO and sick leave.

Learning budget: Buy books, take classes, and attend conferences with a $2k per year learning budget.

Weekly pay: Every Friday is payday! Just one perk of being your own payroll provider.

Paid family leave: 16 weeks of paid leave for new parents and flexible return-to-work options.

Health benefits: High quality health, dental, and vision insurance coverage.

Risks

Increased competition from new entrants may lead to pricing pressures and reduced market share.

Managing payroll across 11,000 jurisdictions risks compliance errors and potential legal penalties.

Reliance on partner platforms means disruptions could directly impact Check's revenue streams.

Differentiation

Check pioneered embedded payroll, allowing platforms to create custom payroll services.

Check's API simplifies payroll across 11,000 U.S. jurisdictions, reducing administrative burdens.

Check partners with leading platforms like Homebase and Bambee, enhancing their payroll offerings.

Upsides

Partnership with Wave expands Check's reach to 300,000 small businesses across the U.S.

Fraud protection tools enhance Check's value proposition for small and medium-sized businesses.

Novo's integration of Check's API highlights the trend of embedded finance, boosting customer retention.

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