# Benefits & Payroll Lead

**Company:** [Upside](https://hotfix.jobs/companies/upside)
**Location:** Washington, DC, New York, NY
**Role:** People Ops
**Salary:** $153k – $183k/yr
**Experience:** 8+ years
**Skills:** Payroll Administration, Benefits Administration, Multi-State Payroll, Payroll Tax Compliance, Erisa Compliance, Aca Compliance, Cobra Compliance, Hipaa Compliance, Bamboohr, HRIS
**Posted:** 2026-04-06

> Lead payroll and benefits operations for a growing company, managing end-to-end semi-monthly payroll across multiple states and overseeing comprehensive benefits programs while ensuring compliance.

## Job Description

## Payroll
- Manage and execute end-to-end semi-monthly payroll for 250+ U.S.-based employees across 30 states, ensuring accuracy in earnings, deductions, and taxes
- Handle regular and off-cycle payroll, including bonuses, equity, terminations, and other complex scenarios
- Own payroll tax compliance across federal, state, and local jurisdictions, including filings, reconciliations, audits, and resolution of tax notices
- Lead 401(k) audits and workers’ compensation filings
- Oversee quarterly and annual filings (e.g., 941s, FUTA, SUTA) and ensure timely reporting
- Partner with Finance on payroll accounting, accruals, journal entries, and close processes
- Maintain strong internal controls and documentation to support compliance and audit readiness
- Continuously improve payroll workflows, systems configuration, and data integrity
- Support and resolve complex payroll questions and issues

## Benefits
- Oversee the administration of health, retirement, leave, and ancillary benefit programs
- Lead Open Enrollment planning and execution, including vendor coordination and employee communications
- Ensure compliance with ERISA, ACA, COBRA, HIPAA, and applicable regulations
- Manage relationships with brokers and third-party administrators to maintain high service quality
- Monitor regulatory changes and implement updates as needed
- Continuously improve benefits workflows, system configuration, and data integrity
- Support and resolve complex benefits-related questions

## What You Bring
- 8+ years of hands-on experience in payroll and benefits administration in a multi-state environment
- Experience in independently running payroll operations end-to-end
- Strong knowledge of U.S. payroll tax regulations and benefits compliance
- Strong analytical and problem-solving skills
- High attention to detail and a commitment to accuracy
- Ability to communicate complex information clearly to a wide range of audiences
- Sound judgment and discretion when handling sensitive employee data
- Experience with HRIS and payroll systems (e.g., BambooHR)
- CPP, CEBS, or similar certifications are a plus

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