People Operations Lead: Payroll, Benefits & Compliance

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

Benefits offered by this job

Work from home

Flexible Paid Time Off policy

Flexible hours

Competitive salary

Commuter benefits

Company stock options

401k

Medical, dental, and vision insurance

Disability insurance

Life and AD&D insurance

Free One Medical membership

Paid parental leave for all parents

Regular virtual team events

Co-working/remote budgets

Home office budget

Referral bonuses

Professional development budget

Claude AI account

Job summary

FreeWill seeks a People Operations Manager to own the operational and compliance backbone of the employee experience. You will oversee payroll, benefits administration, onboarding, offboarding, and regulatory reporting across multiple states and countries.

Reporting to the People and Culture Lead, you’ll partner with Finance, benefits brokers, and vendors to ensure accurate pay, compliant processes, and seamless employee support from day one through exit, including EOR and international benefits

Qualifications

• 6+ years of benefits and payroll administration experience, including end-to-end program ownership.

Responsibilities

• Collaborate with People, 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 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.
• 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.

Skills

Payroll administration

Benefits administration

Regulatory reporting

Vendor management

HRIS (Justworks)

Employee lifecycle

Project management

Data accuracy

Education

Bachelor’s degree (HR or related)

Tools

Justworks

EOR management

HRIS systems

Job description

FreeWill seeks a People Operations Manager to own the operational and compliance backbone of the employee experience. You will oversee payroll, benefits administration, onboarding, offboarding, and regulatory reporting across multiple states and countries.

Reporting to the People and Culture Lead, you’ll partner with Finance, benefits brokers, and vendors to ensure accurate pay, compliant processes, and seamless employee support from day one through exit, including EOR and international benefits