Payroll and Benefits Specialist

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Two Chairs

WebsiteLinkedInAll Job Openings

201 - 500 employees

⚕️ Healthcare Insurance

🧘 Wellness

💰 $23M Series B on 2019-08

Healthcare Insurance • Wellness

Two Chairs is a company that offers psychotherapy services with a focus on matching clients with the right therapist to build a strong therapeutic alliance. Currently serving California, Florida, and Washington, Two Chairs provides individual therapy through a combination of virtual and in-person sessions. The company emphasizes the importance of the client-therapist relationship and offers a structured matching process with licensed experts to understand each client's unique needs and preferences. With a diverse team of therapists representing over 90 areas of clinical expertise, Two Chairs is committed to providing personalized mental health care.

📋 Description

• 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 paychecks for terminating employees • Manage state registration and employment taxes through our HRIS and in partnership with local municipalities • Recommend improvements to Two Chairs’ current payroll procedures for increased scalability and accuracy as we expand into new, more complex markets • Ensure all payroll processes align with federal, state, and local labor laws and tax regulations • Support internal and external payroll audits (e.g 401k 5500) • Partner closely with Finance and People Business Partners on payroll-adjacent workflows including leaves, terminations, and some benefit-related needs • Provide first-line support for employee questions regarding health, dental, vision, FSA/HSA, 401(k). • Assist with benefits enrollments, life event updates, and employer offerings by coordinating with external vendors. • Conduct audits of benefits data to ensure accuracy in billing, eligibility, and payroll deductions. • Support compliance activities, including ACA reporting, 401(k) audits, and state/federal requirements. • Partner with brokers, vendors, and internal stakeholders to research and resolve benefits discrepancies. • Respond to employee inquiries through the People Team ticketing system, ensuring accurate and timely resolution. • Provide support across a wide range of People Operations workflows—including onboarding, offboarding, and transfers—by ensuring payroll, benefits, and employee data are accurate and up to date. This role also offers opportunities to contribute to process improvements and cross-functional projects. • Maintain accurate employee records and documentation across HRIS, payroll, and benefits platforms. • Support reporting and data needs by building and maintaining standard People Operations reports, assisting with audits, and ensuring leadership has accurate, timely insights into payroll, benefits, and employee data.

🎯 Requirements

• At least 2 years of experience in an HR role at a startup or fast-paced company environment • Experience supporting payroll and affiliated state taxes - Rippling experience strongly preferred • Strong attention to detail with a desire to enhance processes for scalability • Ability to work independently and multitask • Thrive and live by operational excellence - you’re able to prioritize across many stakeholders without dropping the ball • Great team player with a collaborative approach • Strong technical, analytical, written, and verbal communication skills • Highly organized and able to stay on top of tasks in a complex environment • Comfortable operating with ambiguity in a complex environment, and escalating appropriately when needed • Working knowledge of federal and state wage and hour laws, with experience navigating multi-state compliance.

🏖️ 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