Two Chairs

Healthcare

Manager,Payroll&BenefitsOperations

$130–145k Remote FULL TIME Remote Friendly
Market Sentiment
HIGH DEMAND

Neural analysis suggests this role is
optimal for Manager candidates.

The Brief

“Manager, Payroll & Benefits Operations at Two Chairs. Skills: Payroll operations, Benefits administration. Audit carrier invoices against payroll deductions. Audit carrier invoices against enrollment data”

What You'll Achieve.

Identify immediate opportunities for process improvement; Provide actionable insights to leadership; Support a scalable, high-growth environment

Industry & Context.

Healthcare
Problems you'll solve

Resolve discrepancies; Simplify complexity

What They're Looking For.

Must Have

Demonstrated professional expertise in managing complex, multi-state payroll operations, Hands-on experience in benefits operational administration, Advanced knowledge of financial systems, Advanced knowledge of payroll platforms, Experience supporting employee payroll and benefits in California, Exceptional attention to detail, Commitment to maintaining data integrity, Commitment to maintaining confidentiality, Excellent written communication skills, Excellent verbal communication skills, Proven ability to manage multiple projects, Proven ability to build structured processes from the ground up, Demonstrated systems thinking, Solution-oriented approach to simplifying complexity, Proven track record of improving processes, Proven track record of enabling organizational scale

Nice to Have

Experience with Rippling, Experience with Tilt, Working knowledge of payroll regulations, Working knowledge of benefits regulations, Experience with ERISA, Experience with COBRA, Experience with ACA, Experience with FMLA

What You'll Do.

Audit carrier invoices against payroll deductions

Audit carrier invoices against enrollment data

Resolve discrepancies

Ensure timely resolution of benefits questions

Ensure accurate resolution of benefits questions

Oversee payroll for employees on leave

Oversee benefits for employees on leave

Partner with carriers to resolve escalated claims issues

Partner with carriers to resolve enrollment discrepancies

Partner with brokers to resolve escalated claims issues

Partner with brokers to resolve enrollment discrepancies

Partner with TPAs to resolve escalated claims issues

Partner with TPAs to resolve enrollment discrepancies

Partner with People Team leadership to execute Open

Ensure system configuration for Open Enrollment

Ensure employee communications for Open Enrollment

Ensure data transfers to carriers for Open Enrollment

Complete audit of current payroll workflows

Identify opportunities for process improvement

Establish working relationships with Finance

Establish working relationships with People departments

Demonstrate mastery of Two Chairs' payroll systems

Demonstrate mastery of internal policies

Streamline recurring payroll tasks

Automate recurring payroll tasks

Implement advanced payroll reporting

Implement advanced payroll analytics

Model Two Chairs management standards

Effectively manage direct reports

Effectively manage project-based teams

How You'll Work.

Team & Collaboration

Key stakeholders in Finance; Key stakeholders in People departments; People Team leadership

Communication Scope

Articulate actionable conclusions

Process & Methodology

Manage multiple projects, Build structured processes

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 As the Manager, Payroll 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 Impact and Success Indicators Where you’ll make an impact in the first 90 days: Complete a comprehensive audit of current payroll workflows and identify immediate opportunities for process improvement. Establish strong working relationships with key stakeholders in the Finance and People departments. Demonstrate mastery of Two Chairs' payroll systems and internal policies. Where you’ll make an impact in the first year: Streamline and automate recurring payroll tasks to support a scalable, high-growth environment. Implement advanced payroll reporting and analytics to provide actionable insights to leadership. Model Two Chairs management standards by effectively managing direct reports or pro

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