Payroll and Benefits Specialist

About the role

We’re looking for a detail-oriented Payroll & Benefits Specialist to join our People Operations team. In this role, you’ll help keep our payroll and benefits operations running smoothly while supporting employees across a growing number of states. You’ll own day-to-day payroll execution, assist with benefits administration and compliance processes, and serve as a go-to resource for employee questions, helping create a seamless employee experience.

You’ll gain hands-on experience across payroll preparation, benefits administration, compliance audits, and core HR operations while also contributing to People Operations projects that improve and scale our processes. This is an exciting opportunity for someone who cares about accuracy, enjoys building efficient systems, and is eager to grow a long-term career in People Operations.

Core Areas of Responsibility

• Payroll Execution
  • 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
• Compliance and Operations
  • 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
• Benefits & Compliance Support
  • 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.
• People Operations & Employee Support
  • 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, a