Payroll and Benefits Manager

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 & Benefits Operations at Two Chairs, you will lead the end-to-end execution and optimization of our payroll function while driving the operational execution, compliance and day-to-day management of our benefits programs. Reporting to the Senior Director, People Partners & Programs, you will serve as a critical bridge between the Finance and People teams, ensuring our rapidly growing team is paid accurately and on time while maintaining the highest standards of compliance. You will be the subject matter expert for all payroll-related inquiries and will play a pivotal role in scaling our systems to support long-term growth.

Core Areas of Responsibility

• Payroll Execution and Data Integrity




• 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.




• Compliance and Operational Excellence




• 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.




• System Strategy and Cross-functional Collaboration




• 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.




• Benefits Operations




• 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

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 project-based teams.

We’re looking for someone with:

• 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.

Compensation & Benefits

The offer range is dependent on qualifications and experience. New hires can reasonably expect an offer between $129,800 and $145,000.

Additional perks and benefits:

• Equity in a high-growth start-up


• Paid time off, including nine paid holidays and an additional Winter Office Closure from Christmas Day (Observed) through New Year's Day


• Comprehensive medical, dental, and vision coverage


• 401(k) Retirement savings options


• One-time $200 Work from Home reimbursement


• Annual $1,000 Productivity & Wellness Stipend to support your personal and professional goals


• Annual $500 subsidized company contribution to your healthcare FSA or HSA


• Paid parental leave

Outreach Notice to Applicants

We are thrilled that you’re interested in joining our team! To ensure a consistent and equitable hiring process for all candidates, we kindly ask that you refrain from reaching out to current employees regarding the role, your application, or the interview process. Our talent acquisition team is committed to carefully reviewing all applications and will reach out directly if they decide to move forward.

All applicants must be authorized to work for ANY employer in the U.S. We are unable to sponsor or take over sponsorship of an employment Visa at this time.