Remote People Operations Lead: Payroll & Benefits

FreeWill; United States; Remote; USD 95,000 - 105,000; Full time

Benefits offered by this job

Work from home

Flexible PTO policy

Flexible hours

Competitive salary

Commuter benefits

Company stock options

401k

Medical/Dental/Vision benefits

Disability insurance

Life and AD&D insurance

Free One Medical membership

Paid parental leave

Job summary

FreeWill is seeking a People Operations Manager to own the benefits, payroll, and HRIS backbone of the employee experience. You’ll ensure accurate pay, benefits enrollment, and compliant processes from day one to offboarding across a fully remote, US-wide team.

You’ll partner with Finance, benefits brokers, and vendors to optimize programs, while driving open enrollment, ACA, 401(k), and global contractor management with a strong focus on data integrity and employee support.

Qualifications

• 6+ years of benefits and payroll administration experience, including ownership of programs end to end.
• Experience in a fast-paced, dynamic environment in an organization with under 500 employees.
• Deep working knowledge of benefits compliance, including 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, plus if you’ve worked in a global working environment
• 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 are accurate and up to date
• Strong project management and execution skills, with the ability to run multiple recurring processes at once
• Laser-focused attention to detail and a high bar for data accuracy
• A highly adaptable, empathetic individual who enjoys working in a fast-moving, ever-changing environment
• Alignment with FreeWill values of kindness, focus, joy, and courage

Responsibilities

• Own benefits administration programs end-to-end and liaise with brokers for international benefits.
• Manage payroll deductions and changes within our PEO and run semi-monthly reconciliations.
• Keep HRIS (Justworks) data accurate and oversee I-9 & E-Verify checks for new hires.
• Oversee onboarding/offboarding and training coordination, plus annual ACA and 401(k) compliance.
• Handle contract and international employee lifecycle via EOR arrangements like Deel.
• Lead annual open enrollment and benefits communications, plus quarterly reporting and audits.
• Collaborate with Finance and other departments on payroll accuracy and process improvements.

Skills

Benefits administration

Payroll administration

HRIS management

Regulatory compliance

Project management

Wage & hour compliance

Vendor management

EOR management

Employee lifecycle

Attention to detail

Empathy

Tools

Justworks

Ashby

Deel

Job description

FreeWill is seeking a People Operations Manager to own the benefits, payroll, and HRIS backbone of the employee experience. You’ll ensure accurate pay, benefits enrollment, and compliant processes from day one to offboarding across a fully remote, US-wide team.

You’ll partner with Finance, benefits brokers, and vendors to optimize programs, while driving open enrollment, ACA, 401(k), and global contractor management with a strong focus on data integrity and employee support.