[Remote] Payroll Manager at Sidecar Health

Remote

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Not SpecifiedCompensation

Junior (1 to 2 years)Experience Level

Full TimeJob Type

UnknownVisa

Health InsuranceIndustries

Requirements

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

Responsibilities

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

Skills

Key technologies and capabilities for this role

Payroll ProcessingComplianceData EntryReportingFinancial AccuracyPayroll SystemsReconciliation

Questions & Answers

Common questions about this position

What experience level is required for the Payroll Manager role?

The role requires 5+ years of payroll processing experience, preferably in a lead or senior role within a fast-paced environment, along with strong experience managing payroll in a startup or high-growth company.

Where do candidates need to reside for this position?

Candidates must reside in California, Connecticut, Florida, Georgia, New York, Ohio, Texas, Utah, or Washington for consideration.

What key skills are needed for payroll processing in this role?

Expertise with salary, hourly, and commission-based payroll calculations and multi-entity structures, plus deep knowledge of payroll compliance, are essential.

What is the company culture like at Sidecar Health?

Sidecar Health has a passionate team from diverse backgrounds like tech leaders, policy makers, and healthcare professionals, all driven to fix a broken healthcare system in a startup environment.

What makes a strong candidate for this Payroll Manager position?

A strong candidate has 5+ years of payroll experience in a lead role, expertise in multi-entity payroll and compliance, and thrives in a fast-paced startup scaling operations.

Sidecar Health

Affordable health insurance with price transparency

About Sidecar Health

Sidecar Health provides health insurance plans that focus on affordability and transparency, including options compliant with the Affordable Care Act (ACA). The company allows members to see average cash prices for medical services upfront, helping them make informed decisions and avoid unexpected costs. Revenue is generated through member premiums, which cover medical expenses, while also benefiting from the difference between negotiated cash prices and premiums. Sidecar Health's goal is to empower members to take control of their healthcare expenses with straightforward and cost-effective insurance options.

El Segundo, CaliforniaHeadquarters

2018Year Founded

$319.1MTotal Funding

SERIES_DCompany Stage

Financial Services, HealthcareIndustries

201-500Employees

Benefits

Health Insurance

Dental Insurance

Vision Insurance

401(k) Retirement Plan

Paid Vacation

Paid Holidays

Stock Options

Company Equity

Risks

Increased competition from similar insurtech companies may erode market share.

Regulatory scrutiny on cash pay models could pose compliance challenges.

Economic downturns might reduce consumer spending on health insurance premiums.

Differentiation

Sidecar Health offers transparent pricing, empowering members with upfront healthcare cost information.

The company provides customizable plans, aligning with individual coverage needs and budgets.

Partnerships with institutions like Ohio State University enhance their fixed-price care model.

Upsides

Recent $165M Series D funding supports expansion and innovation in health insurance.

Partnership with Mark Cuban Cost Plus Drug Company lowers prescription drug costs for members.

ACA-compliant product line expansion increases market reach and consumer options.

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