People Operations Manager (Benefits & Payroll)

About this role

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 https://www.newsweek.com/rankings/most-loved-workplaces-2024 and Best Practice Institute https://mostlovedworkplace.com/americas-top-most-loved-workplaces-2/ and the 2025 Most Loved Workplaces® for Diversity https://email.bestpracticeinstitute.org/b?y=49ii4eh26ormacb36ss66o9ickp3cp1g60oj2opjclgj8ch25gh748hq49k78t3gect2ubrddtpn8r3fepim8trfe9ln0r31cdiisorfdknn8rrg5lmmusrk5lm6utj5cgmnerriddo6oob3clpiqpjfe8mm8qbmclp76qbkf4ni4=== by the Best Practice Institute. In 2026, we were named as one of Forbes' Best Startup Employers https://www.forbes.com/lists/americas-best-startup-employers/.

Curious about company culture and management at FreeWill? Check out the 2025 Best Manager Ever podcast https://www.linkedin.com/posts/annie-riley_best-manager-ever-season-2-is-here-and-activity-7310682359555608576-SB_S?utm_source=share&utm_medium=member_desktop&rcm=ACoAABnmpFEBcS1To2bUTjEfnYw_acY6KJgksEw featuring Anthony Sottile, FreeWill's VP of Partner Success on either Spotify https://open.spotify.com/episode/4sF3EVtJTZLWanpdyKUhR7?si=db352cf2708242bd&nd=1&dlsi=5ed355e404ed468aor Apple https://podcasts.apple.com/us/podcast/best-manager-ever-anthony-sottile-embracing-failures/id1772958574?i=1000700880156.

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…