People Operations Manager (Benefits & Payroll)

About Us

FreeWill is an award-winning, social-good startup that has partnered with 2,400+ nonprofits who support our mission while generating $14B in gift commitments for nonprofits since we were founded in 2017. We’ve been featured in the New York Times, Forbes, Oprah’s magazine, and our co-CEOs have even been named to Town & Country’s “Top 50 Philanthropists” list.

All of this is because we’ve figured out how to make some powerful (but complicated!) ways to donate much easier and more accessible. Our products make things easier for the donors who want to change the world and for nonprofits doing heroic work around the planet. We partner with nonprofits of all sizes to diversify fundraising across individual and institutional giving, from legacy gifts and tax-smart donations to foundation, corporate, and government grants.

In the last 9 years, we’ve grown from 5 people to 200+ (all smart, tenacious, and kind), and continue to grow. We’d love to have you be a part of this adventure. We were named a "Most Loved Workplace" by both Newsweek and Best Practice Institute and the 2025 Most Loved Workplaces® for Diversity by the Best Practice Institute. In 2026, we were named as one of Forbes' Best Startup Employers .

Curious about company culture and management at FreeWill? Check out the 2025 Best Manager Ever podcast featuring Anthony Sottile, FreeWill's VP of Partner Success on either Spotify or Apple .

About the role

We are 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 make sure our people are paid accurately, enrolled in benefits, and supported through every change in their employment — from their first day to their last. It 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 the compliance airtight. You'll own our relationship with our benefits broker and vendors, partner closely with Finance, and be the trusted go-to for employee questions about pay and benefits.

This role reports directly to our People and Culture Lead.

This is a full-time remote position. The offers for this role will be in the range of $95,000-$105,000 per year and includes full benefits and equity.

Responsibilities

Collaborating with other members of the People team (Recruitment, HR), Finance, and other departments on joint projects and where applicable

Benefits Administration:

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, from planning through post-open enrollment benefits administration

Partner with our insurance broker on health insurance renewals, including plan negotiations, plan cost analysis, claim spending analysis through a level-funded insurance plan

Manage FSA/HSA spend-account benefits, including monthly funding and invoicing

Facilitate qualifying life events (QLEs) enrollment

Partner with our third-party COBRA administrator for all employee exits

Own annual ACA filing and compliance, 401(k) compliance, and monthly benefits reporting

Keep employee-facing benefits resources current on FreeWill's employee intranet

Collect employee feedback on benefit offerings and propose improvements to total benefits packages including perk benefits

Payroll Administration:

Partnering with the finance team where applicable

Manage employee deductions and payroll modifications within our PEO

Run payroll reconciliation semi-monthly to verify accuracy

Process leave and PTO-related payment adjustments

Process off cycle payments, including retroactive pay/pay corrections and bonuses

HRIS Management & Employee Lifecycle:

Own responsibility for keeping our HRIS, Justworks, as our accurate source of truth on employee data - — including managing all changes, new hires, manager changes, wage rate and variable compensation changes, title changes, and all other employee data changes, terminations

Audit the HRIS system regularly to ensure data accuracy

Manage I-9 and E-Verify completion and background checks (Checkr) for new hires

Respond to requests for employment verifications

Management of our onboarding system (Ashby) + new hire checklists. Assist with scheduling company required training for employees for the first few weeks.

Manage the full offboarding process for voluntary and involuntary exits, including documentation and final-pay tasks

Manage and track severance agreements and payouts with discretion and compliance

Compliance & Regulatory Reporting:

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 as required by state law

Track and stay current on federal, state, and local employment law changes relevant to our staff — FreeWill's team of nearly 200 is fully remote, working across 30+ states and 4 countries

Contractors & International Employees:

Manage the contractor and international Employer of Record (EOR) population employment life cycle end to end

Facilitate new contractor hires and track contract renewal reminders, maintaining a contractor roster

Manage the employee lifecycle for international staff, including work through Deel and Justworks EOR, ensuring compliance

Other Tasks and Special Projects:

Monitor company’s digital mailbox (which contains mostly state and labor related mailings), forward all other mailings to relevant departments within FreeWill

Owning 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 (e.g., task management for annual 360 and annual review processes)

Required Skills and Experience

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

Benefits

In addition to the immense personal and professional satisfaction you’ll gain from helping to raise $1T for high impact nonprofits in a kind and joyful work environment, full time employees at FreeWill are eligible for the following benefits:

Work from home

Flexible Paid Time Off policy. We trust staff to manage their own schedules and take the time off you need to be your best, as long as your work is on track. We recom