Two Chairs
Healthcare
PayrollandBenefitsSpecialist
Neural analysis suggests this role is
optimal for Mid+ candidates.
“Payroll and Benefits Specialist at Two Chairs. Skills: Payroll, Benefits, HR Operations, Compliance. Process bi-monthly payroll. Ensure payroll accuracy”
What You'll Achieve.
Process payroll on time; Process payroll accurately; Reduce paycheck inquiries; Reduce paycheck escalations; Ensure multi-state compliance proactive; Handle new state registrations; Handle tax changes; Handle mandated updates
Industry & Context.
Resolve benefits discrepancies; Ensure accurate and timely resolution
Authorized to work in U.S
What They're Looking For.
Must Have
5+ years payroll experience, Experience with HRIS, Experience with payroll platforms, Experience with benefits administration, Experience with compliance processes, Experience supporting employees, Experience with payroll preparation, Experience with benefits administration, Experience with compliance audits, Experience with core HR operations, Experience with People Operations projects, Experience with process improvement, Experience with scaling processes, Experience with bi-monthly payroll, Experience with timecard data, Experience with employee questions, Experience with bonuses, Experience with retroactive pay, Experience with final paychecks, Experience with state registration, Experience with employment taxes, Experience with HRIS, Experience with local municipalities, Experience with federal labor laws, Experience with state labor laws, Experience with local labor laws, Experience with federal tax regulations, Experience with state tax regulations, Experience with local tax regulations, Experience with payroll audits, Experience with 401k audits, Experience with Finance, Experience with People Business Partners, Experience with leaves, Experience with terminations, Experience with benefits-related needs, Experience with employee questions, Experience with health benefits, Experience with dental benefits, Experience with vision benefits, Experience with FSA/HSA, Experience with 401(k), Experience with benefits enrollments, Experience with life event updates, Experience with employer offerings, Experience with external vendors, Experience with benefits data audits, Experience with billing accuracy, Experience with eligibility, Experience with payroll deductions, Experience with ACA reporting, Experience with 401(k) audits, Experience with state requirements, Experience with federal requirements, Experience with brokers, Experience with vendors, Experience with employee inquiries, Experience with People Team ticketing system, Experience with onboarding, Experience with offboarding, Experience with transfers, Experience with employee data accuracy, Experience with People Operations workflows, Experience with process improvements, Experience with cross-functional projects, Experience with employee records, Experience with documentation, Experience with HRIS platforms, Experience with payroll platforms, Experience with benefits platforms, Experience with reporting, Experience with data needs, Experience with People Operations reports, Experience with audits, Experience with leadership insights, Experience with payroll data, Experience with benefits data, Experience with employee data, Experience with exempt employees, Experience with non-exempt employees, Experience with full-time clinicians, Experience with part-time clinicians, Experience with variable pay, Experience with payroll cycles, Experience with benefits data audit, Experience with payroll data audit, Experience with centralizing payroll, Experience with centralizing benefits
Nice to Have
Rippling experience strongly preferred
What You'll Do.
Process bi-monthly payroll
Ensure payroll accuracy
Ensure payroll timeliness
Ensure payroll compliance
Reconcile timecard data
Calculate retroactive pay
Process retroactive pay
Calculate final paychecks
Process final paychecks
Manage state registration
Manage employment taxes
Recommend payroll procedure improvements
Ensure payroll processes align with laws
Support payroll audits
Support benefits audits
Partner with People Business Partners
Provide employee benefits support
Assist with benefits enrollments
Assist with life event updates
Assist with employer offerings
Coordinate with external vendors
Conduct benefits data audits
Support compliance activities
Support ACA reporting
Support 401(k) audits
Support state requirements
Support federal requirements
Resolve benefits discrepancies
Respond to employee inquiries
Provide People Operations workflow support
Ensure payroll data accuracy
Ensure benefits data accuracy
Ensure employee data accuracy
Maintain employee records
Maintain documentation
Support reporting needs
Build People Operations reports
Maintain People Operations reports
Ensure leadership has insights
How You'll Work.
Team & Collaboration
Partner with Finance; Partner with People Business Partners; Coordinate with vendors; Cross-functional projects
Full Job Description
Two Chairs is building a new kind of mental health system based on the idea that the status quo isn’t good enough. Industry-best clinician experiences, better client outcomes, groundbreaking innovation, and access to the highest quality care are how we’ll raise the bar for the entire industry. With that, we're excited and honored to have been recognized as a 2025 Great Place to Work and 2025 Fortune’s Best Workplaces in Healthcare. One of our company values is "Embrace Differences" and diversity, equity, inclusion, and belonging are the principles guiding how we build our business and teams. We encourage interested candidates from all backgrounds to apply even if they don't think they meet some expectations of the role. 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 paycheck
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