Payroll and Benefits Specialist

Two Chairs

Payroll and Benefits Specialist joining Two Chairs to support payroll execution and benefits administration. Ensuring compliance and providing employee support for a seamless experience.

Posted 6/8/2026full-timeRemote • 🇺🇸 United StatesJuniorMid-Level💰 $70,000 - $85,000 per yearWebsite

About the role

Key responsibilities & impact

Process bi-monthly company-wide payroll, ensuring accuracy, timeliness, and compliance
Review, verify, and reconcile timecard data (hours, OT, paid time off, and leave of absence balances)
Serve as the primary point of contact for employee questions regarding paychecks, deductions, and tax withholdings
Calculate and process bonuses, retroactive pay, and final paychecks for terminating employees
Manage state registration and employment taxes through our HRIS and in partnership with local municipalities
Recommend improvements to Two Chairs’ current payroll procedures for increased scalability and accuracy as we expand into new, more complex markets
Ensure all payroll processes align with federal, state, and local labor laws and tax regulations
Support internal and external payroll audits (e.g 401k 5500)
Partner closely with Finance and People Business Partners on payroll-adjacent workflows including leaves, terminations, and some benefit-related needs
Provide first-line support for employee questions regarding health, dental, vision, FSA/HSA, 401(k).
Assist with benefits enrollments, life event updates, and employer offerings by coordinating with external vendors.
Conduct audits of benefits data to ensure accuracy in billing, eligibility, and payroll deductions.
Support compliance activities, including ACA reporting, 401(k) audits, and state/federal requirements.
Partner with brokers, vendors, and internal stakeholders to research and resolve benefits discrepancies.
Respond to employee inquiries through the People Team ticketing system, ensuring accurate and timely resolution.
Provide support across a wide range of People Operations workflows—including onboarding, offboarding, and transfers—by ensuring payroll, benefits, and employee data are accurate and up to date. This role also offers opportunities to contribute to process improvements and cross-functional projects.
Maintain accurate employee records and documentation across HRIS, payroll, and benefits platforms.
Support reporting and data needs by building and maintaining standard People Operations reports, assisting with audits, and ensuring leadership has accurate, timely insights into payroll, benefits, and employee data.

Requirements

What you’ll need

At least 2 years of experience in an HR role at a startup or fast-paced company environment
Experience supporting payroll and affiliated state taxes - Rippling experience strongly preferred
Strong attention to detail with a desire to enhance processes for scalability
Ability to work independently and multitask
Thrive and live by operational excellence - you’re able to prioritize across many stakeholders without dropping the ball
Great team player with a collaborative approach
Strong technical, analytical, written, and verbal communication skills
Highly organized and able to stay on top of tasks in a complex environment
Comfortable operating with ambiguity in a complex environment, and escalating appropriately when needed
Working knowledge of federal and state wage and hour laws, with experience navigating multi-state compliance.

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

payroll processingtimecard reconciliationbonus calculationHRIS managementbenefits enrollmentdata auditingACA reportingmulti-state compliancepayroll auditsemployee record maintenance

Soft Skills

attention to detailoperational excellenceindependent workmultitaskingcollaborationanalytical skillswritten communicationverbal communicationorganizational skillsadaptability