People Operations Manager

FreeWill is a mission-driven technology company that helps nonprofits make charitable giving simpler and more accessible.

Since its launch in 2017, the company has partnered with more than 2,400 nonprofit organizations and helped generate billions of dollars in charitable gift commitments.

FreeWill is currently seeking an experienced People Operations Manager to oversee essential HR operations, including payroll, employee benefits, compliance, HR systems, onboarding, offboarding, and support for contractors and international employees.

About the Role

The People Operations Manager will be responsible for maintaining the operational and compliance systems that support employees throughout their time with the company.

This position requires someone who is highly organized, detail-oriented, comfortable managing sensitive employee information, and experienced in benefits and payroll administration.

You will work closely with the People, Recruitment, HR, and Finance teams while serving as a key point of contact for employees who have questions about compensation, benefits, employment changes, and other HR-related matters.

Key Responsibilities

Benefits Administration

Manage employee benefits inquiries and serve as a primary point of contact for benefits-related questions.

Oversee annual open enrollment from initial planning through post-enrollment administration and payroll reconciliation.

Work with insurance brokers and benefits providers on health insurance renewals, plan negotiations, cost analysis, and related administrative processes.

Manage FSA and HSA benefits, qualifying life events, COBRA administration, ACA reporting, 401(k) compliance, and recurring benefits reporting.

Maintain accurate and up-to-date benefits information for employees and gather feedback that can help improve the company’s overall benefits package.

Payroll Administration

Work closely with the Finance team to manage payroll-related activities.

Handle employee deductions and payroll changes through the company’s PEO system.

Conduct semi-monthly payroll reconciliations to ensure payments are accurate.

Process adjustments related to PTO, leave, bonuses, retroactive payments, corrections, and other off-cycle payments.

HR Systems and Employee Lifecycle

Maintain accurate employee information within the company’s HRIS, including new hires, compensation changes, promotions, manager changes, job title updates, and employee departures.

Regularly audit HR systems to ensure employee information remains accurate.

Manage employment verification requests, background checks, I-9 and E-Verify requirements, onboarding systems, and new-hire checklists.

Coordinate both voluntary and involuntary employee exits, including required documentation, final payments, severance agreements, and related administrative responsibilities.

Compliance and Regulatory Reporting

Manage regulatory filings such as EEO-1 reporting and help maintain compliance with applicable employment regulations.

Monitor federal, state, and local employment-law requirements affecting a distributed workforce.

Coordinate required workplace training, including anti-harassment and anti-discrimination programs.

Support wage-and-hour compliance and employment verification processes.

Contractors and International Employees

Oversee the employment lifecycle for contractors and international team members.

Coordinate new contractor onboarding, maintain contractor records, and monitor contract renewal dates.

Support international employment processes through platforms such as Deel and Justworks EOR while helping ensure applicable compliance requirements are followed.

Additional Responsibilities

Maintain HR documentation, procedures, and internal processes.

Monitor employment-related correspondence and route relevant information to appropriate departments.

Support operational, compliance, and HR systems projects as the organization continues to grow.

Assist with recurring People & Culture initiatives, including annual reviews and 360-degree feedback processes.

Required Experience and Skills

Candidates should have 6+ years of experience in payroll and benefits administration, including experience independently managing programs from beginning to end.

Strong knowledge of employee-benefit and workplace compliance requirements is required, including areas such as ACA, COBRA, ERISA/401(k), HIPAA, FMLA, and qualifying life events.

Candidates should also have experience with payroll reconciliation, open enrollment, HRIS or PEO systems, vendor and benefits-broker management, regulatory reporting, employee exits, and severance administration.

Experience working with multi-state employees and employment regulations is highly valuable.

The ideal candidate will have strong project-management abilities, excellent attention to detail, a high standard for data accuracy, and the ability to manage several recurring responsibilities simultaneously.

You should also be adaptable, empathetic, dependable, and comfortable working in a fast-moving organization.

Benefits

Full-time employees may receive a comprehensive package that includes:

Work-from-home flexibility, flexible working hours, flexible paid time off, company stock options, 401(k), medical, dental and vision coverage, short- and long-term disability insurance, life and AD&D insurance, One Medical membership, and paid parental leave.

Employees also receive a $250 monthly coworking/home Wi-Fi budget, a $300 annual home-office or utility allowance, and an $800 annual professional-development budget.

Hiring Process

The expected recruitment process includes a 30-minute hiring manager interview, a one-hour take-home assignment, a panel interview, a final leadership interview, and an offer subject to satisfactory references.

The company notes that the process may change depending on the position, but hiring generally takes approximately four weeks.

Location and Work Authorization

FreeWill operates as a remote-first organization with employees in the United States, Brazil, Canada, and Pakistan.

Within the United States, the company currently hires across 47 states and Washington, D.C., excluding Colorado, Alabama, and Louisiana.

Visa sponsorship is not available, so applicants must already have appropriate work authorization in their respective country.