Payroll Support Specialist

About the role

The Partner Support Team resolves payroll and payroll tax discrepancies after they occur. As a Payroll Specialist on the Support team, you will own these cases end to end.

Responsibilities

• Investigate the underlying issue, correct historical payroll records, determine the downstream filing and financial impact, and communicate the outcome to our partners.
• Determine which previously submitted filings are affected by a correction and identify the amendments required by period, jurisdiction, and form, providing the filing team with complete and accurate documentation.
• Determine when corrected employee and contractor tax forms, such as W-2C and 1099 corrections, are required, and confirm the corrected figures are accurate before they are issued.
• Reconcile tax accounts by balancing calculated, collected, and filed amounts, and identify the resulting tax due, refund, or credit.
• Determine the financial impact of each correction and initiate the appropriate collection or refund, partnering with internal teams to see it through to completion.
• Assess materiality and filing obligations to determine the appropriate scope of each correction, and document the supporting rationale.
• Communicate correction outcomes, resulting filing changes, tax impact, and expected timelines to partners through clear, accurate, and timely written updates.
• Partner with Tax Operations, Payroll Operations, Engineering, Product, and Risk to resolve complex cases and escalate suspected product defects with complete context.
• Manage a high volume of concurrent cases against filing deadlines and service level commitments, prioritizing by risk and impact.
• Identify recurring root causes and recommend process, documentation, automation, and product improvements that reduce correction volume.

Requirements

• 3–4 years of experience in payroll operations, payroll tax, tax compliance, or a client-facing role supporting a payroll, HR technology, or fintech product.
• Hands-on experience with payroll corrections, account reconciliation, and the amendment process, or comparable experience correcting regulated submissions, including fluency with corrected and amended tax forms.
• Working knowledge of multi-jurisdiction payroll tax, including federal employment taxes, state income tax and unemployment insurance, paid leave and disability programs, annual reconciliations, and local taxes.
• Demonstrated success analyzing data to investigate issues and identify root causes along with resolutions, including advanced spreadsheet proficiency; SQL experience a plus.
• A demonstrated ability to identify process improvements and implement operational solutions at scale, including the use of AI tooling to automate workflows while validating for accuracy.
• Experience with ticketing and/or case management systems, especially Zendesk.
• Availability to support Check's operating elevated workload during quarter-end and year-end filing periods, and to attend our annual 3-day company offsite each spring.

Qualifications

• Available to work remotely, hybrid, or in one of our offices in New York City or San Francisco.
• Ability to perform all responsibilities without distraction or disruption, while maintaining quality, effective communication, and productivity.

Skills

• Strong analytical and problem-solving skills.
• Excellent written and verbal communication skills.
• Proficiency in Excel and SQL (optional).

Benefits

• Equal opportunity employer.
• Comprehensive health and wellness benefits.
• Flexible work arrangements.
• Professional development opportunities.
• Regular team offsites and events.
• Annual company retreat.

Pay

$83.3K - $108K

Schedule

Full-time position.