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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

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.

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools
payroll operationsdata analysisemployee data managementbenefits administrationregulatory compliancedata integrityfinancial systemspayroll platformsprocess optimizationproject management
Soft Skills
attention to detailwritten communicationverbal communicationcollaborationproblem-solvingorganizational skillsteamworkadaptabilitystakeholder managementsystems thinking