Payroll and Benefits Specialist

This is a fully remote position, open to applicants in United States.

📋 Description

• Execute bi-monthly payroll for the entire company, ensuring precision, timeliness, and adherence to compliance standards.

• Examine, validate, and reconcile timecard information, including hours worked, overtime, paid time off, and leave of absence balances.

• Act as the main contact for employees with inquiries about paychecks, deductions, and tax withholdings.

• Calculate and issue bonuses, retroactive payments, and final paychecks for departing employees.

• Oversee state registration and employment tax responsibilities through our HRIS in collaboration with local authorities.

• Suggest enhancements to Two Chairs’ payroll procedures to boost scalability and accuracy as we venture into more complex markets.

• Ensure all payroll operations comply with federal, state, and local labor laws and tax regulations.

• Assist with internal and external payroll audits (e.g., 401k 5500).

• Collaborate closely with Finance and People Business Partners on payroll-related workflows, including leaves, terminations, and certain benefit-related tasks.

• Offer initial support for employee inquiries concerning health, dental, vision, FSA/HSA, and 401(k) plans.

• Help manage benefits enrollments, life event updates, and employer offerings by coordinating with external vendors.

• Conduct audits of benefits data to verify accuracy in billing, eligibility, and payroll deductions.

• Assist with compliance efforts, including ACA reporting, 401(k) audits, and adherence to state and federal requirements.

• Collaborate with brokers, vendors, and internal stakeholders to investigate and resolve any discrepancies in benefits.

• Address employee questions through the People Team ticketing system, ensuring prompt and accurate resolutions.

• Provide support across various People Operations workflows—including onboarding, offboarding, and transfers—by keeping payroll, benefits, and employee data accurate and current. This role also allows for contributions to process improvements and cross-functional initiatives.

• Maintain precise employee records and documentation across HRIS, payroll, and benefits platforms.

• Assist with reporting and data requirements by creating and maintaining standard People Operations reports, aiding in audits, and ensuring leadership has timely and accurate insights into payroll, benefits, and employee data.

⛳️ Requirements

• Minimum of 2 years of experience in an HR role within a startup or fast-paced company environment.

• Experience in payroll support and associated state taxes; familiarity with Rippling is highly preferred.

• Exceptional attention to detail with a commitment to improving processes for scalability.

• Ability to work autonomously and handle multiple tasks simultaneously.

• Thrive on operational excellence—capable of prioritizing across various stakeholders without oversight.

• Excellent team player with a collaborative mindset.

• Strong technical, analytical, written, and verbal communication abilities.

• Highly organized and adept at managing tasks in a complex setting.

• Comfortable navigating ambiguity in a complex environment and escalating issues as necessary.

• Working knowledge of federal and state wage and hour laws, with experience in 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 reimbursement for Work from Home expenses.

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

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

• Paid parental leave.