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Salary: USD 95,000 - 105,000 / annual
FreeWill is a social-good startup founded in 2017 that partners with 2,400+ nonprofits and has generated $14B in gift commitments. The company has grown from 5 to 200+ employees and has been recognized as a Most Loved Workplace by Newsweek and the Best Practice Institute, as well as one of Forbes' Best Startup Employers in 2026.
The People Operations Manager will own the operational and compliance backbone of the FreeWill employee experience, managing programs and processes that ensure employees are paid accurately, enrolled in benefits, and supported through their employment lifecycle. This is a high-ownership, detail-critical role reporting directly to the People and Culture Lead.
Key responsibilities include:
Benefits Administration: Serve as the primary contact for employee benefits questions; coordinate with Justworks for international benefits; lead annual open enrollment end-to-end; partner with insurance broker on health insurance renewals including plan negotiations and cost analysis; manage FSA/HSA accounts; facilitate qualifying life events enrollment; partner with COBRA administrator for employee exits; own annual ACA filing and 401(k) compliance; maintain employee-facing benefits resources; collect feedback on benefit offerings.
Payroll Administration: Manage employee deductions and payroll modifications within the PEO; run semi-monthly payroll reconciliation; process leave and PTO adjustments; process off-cycle payments, retroactive pay, and bonuses.
HRIS Management & Employee Lifecycle: Maintain Justworks as the accurate source of truth for employee data; manage all employee data changes, new hires, terminations; audit HRIS regularly; manage I-9 and E-Verify completion and background checks; respond to employment verification requests; manage onboarding system (Ashby) and new hire checklists; manage full offboarding process including severance agreements.
Compliance & Regulatory Reporting: Own EEO-1 and regulatory filings; manage wage & hour compliance; manage required annual trainings; track federal, state, and local employment law changes relevant to FreeWill's remote team across 30+ states and 4 countries.
Contractors & International Employees: Manage contractor and international EOR population lifecycle end-to-end; facilitate new contractor hires; manage employee lifecycle for international staff through Deel and Justworks EOR.
Other: Monitor company digital mailbox for state and labor mailings; own documentation and updating of HR processes; take on operational and compliance initiatives as the company grows.
REQUIREMENTS:
- 6+ years of benefits and payroll administration experience, including end-to-end program ownership
- Experience in fast-paced, dynamic environments in organizations with under 500 employees
- Deep working knowledge of benefits compliance: ACA, COBRA, ERISA/401(k), HIPAA, FMLA, and qualifying life events (QLEs)
- Experience leading annual open enrollment from planning through post-enrollment payroll reconciliation
- Strong payroll administration and reconciliation skills, with comfort handling complex, largely manual adjustments and multi-cycle changes
- Working knowledge of multistate wage & hour law and regulatory reporting, including EEO-1; experience in global working environments preferred
- Vendor and broker management experience, including plan negotiations and analysis
- Experience administering involuntary exits and severance with discretion and compliance
- Experience working in an HRIS and/or PEO, ensuring data and systems accuracy
- Strong project management and execution skills, ability to run multiple recurring processes simultaneously
- Laser-focused attention to detail and high bar for data accuracy
- Highly adaptable, empathetic individual who thrives in fast-moving, ever-changing environments
- Alignment with FreeWill values of kindness, focus, joy, and courage
