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Two Chairs

Payroll and Benefits Manager

Two Chairs

Lead payroll and benefits management for a rapidly growing mental health startup, ensuring compliance and efficiency. Work collaboratively to support operational excellence across finance and people teams.

Posted 6/8/2026full-timeRemote • 🇺🇸 United StatesMid-LevelSenior💰 $129,800 - $145,000 per yearWebsite

ATS Keywords

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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills
payroll operationsdata analysisemployee data managementbenefits administrationregulatory compliancedata integrityfinancial systemspayroll platformsprocess optimizationproject management
Soft Skills
attention to detailwritten communicationverbal communicationcollaborationproblem-solvingorganizational skillsteamworkadaptabilitystakeholder managementsystems thinking
Tools & Technologies
RipplingTiltHRISpayroll systemsbenefits tracking systemsdata reconciliation toolsregulatory filing systemsvendor management systemscommunication platformsaudit tools
Industry Keywords
multi-state payrollERISACOBRAACAFMLAemployee benefitslabor lawsdata confidentialityoperational excellenceopen enrollment

About the role

Key responsibilities & impact
  • Oversee employee data within the HRIS (Rippling) to ensure data integrity, compliance, and proper documentation.
  • Manage sensitive employee data and payroll-related reporting, including data review and analysis on an ongoing basis.
  • Manage end-to-end payroll operations for hourly, salaried, and complex employee structures, collaborating with Data and Finance teams to administer variable pay, bonuses, and clinical compensation models.
  • Ensure all payroll operations comply with federal, state, and local labor laws and reporting requirements.
  • Maintain and improve payroll policies and internal controls to drive operational excellence.
  • Manage year-end payroll activities, including the production and distribution of W-2s and other regulatory filings.
  • Partner with cross-functional stakeholders in Finance, People, and Operations to build effective, efficient systems for the company’s long-term growth.
  • Manage relationships with external payroll vendors and consultants to optimize service delivery.
  • Optimize operational processes to eliminate bottlenecks and support scalable organizational growth.
  • Manage the monthly benefits billing reconciliation process; audit carrier invoices against payroll deductions and enrollment data to ensure accuracy and resolve discrepancies.
  • Ensure timely and accurate resolution of benefits questions.
  • Oversee payroll and benefits tracking for employees on leave.
  • Partner with carriers, brokers and TPAs to resolve escalated claims issues and enrollment discrepancies.
  • Partner with People Team leadership to execute the annual Open Enrollment process, ensuring system configuration, employee communications and data transfers to carriers are handled seamlessly.

Requirements

What you’ll need
  • Demonstrated professional expertise in managing complex, multi-state payroll operations and hands-on experience in benefits operational administration.
  • Advanced knowledge of financial systems and payroll platforms. Experience with Rippling and Tilt are strongly preferred.
  • Strong working knowledge of payroll and benefits regulations, including ERISA, COBRA, ACA and FMLA. Experience supporting employee payroll and benefits in California required.
  • Exceptional attention to detail and a commitment to maintaining data integrity and confidentiality.
  • Excellent written and verbal communication skills, with the ability to articulate actionable conclusions to various stakeholders.
  • A highly collaborative, team-first mentality with a desire to work in a mission-driven startup environment.
  • Proven ability to manage multiple projects at once and build structured processes from the ground up.
  • Demonstrated systems thinking and solution-oriented approach to simplifying complexity.
  • Proven track record of improving processes by simplifying them and enabling organizational scale.