People Operations Manager (Benefits & Payroll)

FreeWill is looking for a People Operations Manager to own the operational and compliance backbone of the FreeWill employee experience. This role is responsible for the programs and processes that ensure employees are paid accurately, enrolled in benefits, and supported through every change in their employment — from their first day to their last. The role spans benefits administration, payroll, compliance and regulatory reporting, contractor and Employer of Record (EOR) management, and the full onboarding and offboarding lifecycle.

This is a high-ownership, detail-critical role for someone who takes pride in getting the numbers right and compliance airtight. You’ll own relationships with benefits brokers and vendors, partner closely with Finance, and be the trusted go-to for employee questions about pay and benefits.

This role reports directly to the People and Culture Lead.

Responsibilities will include:

• Collaborate with People team, Finance, and other departments on joint projects
• Serve as the first point of contact for employee benefits questions
• Coordinate with Justworks for international benefits questions
• Lead annual open enrollment end-to-end, including planning, administration, and post-enrollment tasks
• Partner with insurance broker on health insurance renewals, plan negotiations, and cost analysis
• Manage FSA/HSA spend-account benefits, including monthly funding and invoicing
• Facilitate qualifying life events (QLEs) enrollment
• Partner with third-party COBRA administrator for all employee exits
• Own annual ACA filing and compliance, 401(k) compliance, and monthly benefits reporting
• Maintain employee-facing benefits resources on the intranet
• Collect employee feedback on benefits and propose improvements
• Manage employee deductions and payroll modifications within the PEO
• Run payroll reconciliation semi-monthly to verify accuracy
• Process leave and PTO-related payment adjustments and off-cycle payments
• Maintain HRIS (Justworks) as the accurate source of truth for employee data, including all changes and terminations
• Audit HRIS regularly to ensure data accuracy
• Manage I-9 and E-Verify completion and background checks for new hires
• Respond to employment verification requests
• Manage onboarding system and new hire checklists; assist with scheduling required training
• Manage the full offboarding process, including documentation and final-pay tasks
• Manage and track severance agreements and payouts with discretion and compliance
• Own EEO-1 and other regulatory filings
• Manage wage & hour compliance and employment verification requests
• Manage required annual trainings such as anti-harassment and anti-discrimination
• Track and stay current on federal, state, and local employment law changes relevant to a remote team across 30+ states and 4 countries
• Manage contractor and international EOR population employment lifecycle end to end
• Facilitate new contractor hires and track contract renewals
• Manage employee lifecycle for international staff, including work through Deel and Justworks EOR
• Monitor company’s digital mailbox for state and labor-related mailings
• Own documentation and updating of HR processes, training coverage, and backup as needed
• Take on operational, compliance, and systems initiatives across the People & Culture function as the team and company grow

You’re a great fit if you:

• Have 6+ years of benefits and payroll administration experience, including end-to-end program ownership
• Have experience in a fast-paced, dynamic environment in an organization with under 500 employees
• Possess deep working knowledge of benefits compliance, including ACA, COBRA, ERISA/401(k), HIPAA, FMLA, and QLEs
• Have experience leading annual open enrollment from planning through post-enrollment payroll reconciliation
• Demonstrate strong payroll administration and reconciliation skills, with comfort handling complex, manual adjustments and multi-cycle changes
• Have working knowledge of multistate wage & hour law and regulatory reporting, including EEO-1; global experience is a plus
• Have vendor and broker management experience, including plan negotiations and analysis
• Have experience administering involuntary exits and severance with discretion and compliance
• Have experience working in an HRIS and/or PEO, ensuring data and systems accuracy
• Possess strong project management and execution skills, able to run multiple recurring processes at once
• Have laser-focused attention to detail and a high bar for data accuracy
• Are highly adaptable, empathetic, and enjoy working in a fast-moving, ever-changing environment
• Align with FreeWill values of kindness, focus, joy, and courage

Total Compensation

The projected annual salary range is $95,000 - $105,000 plus equity.

Additional benefits include:

• Work from home
• Flexible Paid Time Off policy (minimum three weeks recommended)
• Flexible hours
• Competitive salary
• Commuter benefits
• Company stock options
• 401k
• Medical, dental, and vision (some single coverage medical plans are 100% employer paid; subsidized rates for dependents)
• Short-term and long-term disability insurance
• Life and AD&D insurance
• Free One Medical membership
• Paid parental leave for all parents

Perks

• Regular (virtual) team events
• $250 monthly co-working budget (for local co-working spaces and home wifi)
• $300 annual home office or utility budget
• $1,000 referral bonuses
• $800 annual professional development budget
• Claude (AI Assistant) company/team account

Hiring Process

• Hiring Manager Interview (30 minutes)
• Take Home Assignment (1 hour)
• Panel interview (30 minutes)
• Final interview with leadership
• Offer (contingent on positive references)

AI Policy

Candidates are expected to demonstrate their experience and skills through their own words and work, not through AI-generated content. Use of AI-generated content during the hiring process is discouraged and may result in not moving forward. Use of AI tools to enhance work is encouraged once hired.

EEOC & Diversity Statement

FreeWill is an equal opportunity employer and values diversity. Employment decisions are not based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, disability status, or any other characteristic protected by law. FreeWill is a remote-first company and cannot sponsor working visas. All applicants must have work authorization in their respective country. If you don’t meet every qualification, you are still encouraged to apply.