Payroll Manager

Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and attainable for everyone. We know that to accomplish this lofty mission, we need driven people who will make things happen.

The passionate people who make up Sidecar Health's team come from all over, with backgrounds as tech leaders, policy makers, healthcare professionals, and beyond. And they all have one thing in common—the desire to fix a broken system and make it more personalized, affordable, and transparent.

If you want to use your talents to transform healthcare in the United States, come join us!

*Must reside in California, Connecticut, Florida, Georgia, New York, Ohio, Texas, Utah, or Washington for consideration*

About the Role

As Payroll Lead, you'll play a critical role in managing our multi-entity payroll operations as we scale. You'll take ownership of processing payroll across diverse employee types and compensation structures, ensuring accuracy and compliance while building efficient systems for our growing team. This is a hands-on role perfect for someone who thrives in a startup environment and wants to make a direct impact on our operations.

What You'll Do

• Process accurate and timely payroll for multiple entities across salary, hourly, and commission-based employees
• Manage end-to-end payroll operations including data entry, calculations, deductions, and comprehensive reporting
• Ensure compliance with federal, state, and local payroll regulations across all entities
• Reconcile payroll accounts, resolve discrepancies, and maintain meticulous financial accuracy
• Prepare and review bi-monthly payroll inputs such as salary adjustments, payroll taxes, deductions, garnishments, and new hires
• Collaborate with HR, Finance, and other departments to ensure seamless payroll operations and cross-functional alignment
• Maintain and optimize payroll systems and processes for efficiency, accuracy, and scalability
• Maintain compensation records, payroll files, and related documentation for all employees
• Manage census reporting and support month-end and year-end payroll activities including tax filings, audits, and compliance reporting
• Record and audit accrued annual leave, sick leave, and other leave balances
• Handle employee payroll inquiries with exceptional internal customer service and problem-solving
• Prepare detailed payroll reports and analytics for management decision-making
• Support month-end and year-end payroll activities including tax filings, compliance reporting, and audit preparedness
• Build scalable payroll infrastructure and documentation to support our high-growth environment

What You'll Bring

• 5+ years of payroll processing experience, preferably in a lead or senior role within a fast-paced environment
• Strong experience managing payroll processes and systems in a startup or high-growth company
• Expertise with salary, hourly, and commission-based payroll calculations and multi-entity structures
• Deep knowledge of payroll compliance requirements, tax regulations, and GAAP standards
• Advanced Excel skills and experience with payroll software systems
• Exceptional attention to detail, accuracy, and strong analytical problem-solving abilities
• Excellent communication skills and ability to work effectively across departments
• Experience with ADP payroll systems preferred
• Multi-state payroll processing experience a plus
• Bachelor's degree in Accounting, Finance, or related field preferred
• Payroll certification (CPP or similar) a plus

What You'll Get

• Competitive salary and comprehensive benefits package
• Comprehensive Medical, Dental, and Vision benefits
• A 401k retirement plan
• Paid vacation and company holidays
• Opportunity to make an impact at a rapidly growing mission-driven company transforming healthcare in the U.S.